Art by Alan Light

Here’s a list of the top grossing comedies from 1990: Home Alone, Kindergarten Cop, Three Men and a Little Lady, Pretty Woman, Problem Child, Look Who’s Talking Too, and Joe Vs. The Volcano. I’m not pointing this out because they’re bad movies. In my opinion, they’re all good to great. But they are movies produced by a culture with a very different sense of humor than the comedy you’ll see on television or in a theater today.

I’m extremely literal and have a difficult time wrapping my head around abstract concepts like Post-Modernism as it applies to art, but for the readers who have an equally difficult time with the idea, and to give this list context and a rubric, I will offer my elementary definition. Post-Modernism is in a sense acknowledging that the thing you are reading or watching is a construction, a product of intention and imagination. When David Foster Wallace takes a page from Pynchon and names a character Rick Vigorous, when a literal cartoon rendering of Alvy Singer breaks the fourth wall to talk to the camera and you, the audience, about what’s happening on screen, when Spike Jonze steps on a splinter in the middle of planting a bomb outside of Karbala, that’s my idea of Post-Modernism. It’s heightened, random, self aware cartoonishness inserted into a preconceived narrative. The world’s sense of humor has been altered by the ways this concept has manifested itself in our discourse over the last three decades.

As with all reasonable lists, this isn’t definitive but intensely personal. I intentionally didn’t involve any of the site’s other writers in its construction or descriptions because in many ways this list is impossible to compile. I have no idea if Quentin Tarantino got the idea of the “Royale with Cheese” bit from an obscure snippet of Godard, or if Ice Cube and DJ Pooh stole Ezel from an old Bernie Mac bit (or, you know, Richard Pryor’s wino), or if Mike Judge cribbed his vision of the future from William Gibson or Terry Gilliam. And in constructing this list, I didn’t care. The cutoff was 1990, so apologies to the important subversive work done by National Lampoon, Woody Allen, SCTV, Eddie Murphy, Robert Townsend, Harold Ramis, Nora Ephron, Billy Wilder, and Monty Python, among many others.

Off the bat, I would like to acknowledge the glaring lack of women comedians, writers, and directors on this list. I can only apologize for my taste and sense of humor. You may not agree with the rankings and there may be glaring omissions, but ideally, the wide swath here encompasses the major touchtones in comedy over the last 30 years. Large bodies of work and senses of humor are symbolized with a single joke standing in for an entire multi-season television show, a movie career, a comedic viewpoint. These are the formative jokes I couldn’t shake, and watched subsequently shift our idea of what funny is and what funny can be. Enjoy.

Honorable Mentions: Mr. Show and its Russian nesting doll random but connected structure; Brett Favre’s meta cameo in There’s Something About Mary; “Colin the Chicken” from Portlandia; “Grear News!” from Bad Lieutenant 2: Port of Call New Orleans; and “Compliments” from Inside Amy Schumer.

25. Nathan For You (2017) – “Finding Frances”

Potentially the most well constructed long-form joke on this list, it’s either a work of genuinely felt heartbreak, a mean-spirited gag, a cry for help, or some combination of the three. What’s important and special about the finale of Nathan For You’s fourth season is we may never know which is right, to the extent any one of them are. There are two reasons I put it at the end of the list: 1) The danger of recency bias, and 2) Nathan Fielder’s beautiful mind may not prove to be much of an influence. He’s a singular talent, who through his show, has found a medium that may prove hard to find influence in mainstream comedy. Still, what may be the finale of his magnum opus is too brilliant, original, and important to leave out.

I’m not even going to recap it in detail, please read Errol Morris’ New Yorker piece on this then go seek it out for yourself. If you’ve already seen it, watch it again.

24. Super Troopers (2001) – “The Snozberries Taste Like Snozberries”

Something that we’ll see frequently on this list is how conveying group dynamics to film and screen changed comedy. How narrative emphasis shifted from A THING a group of friends need to accomplish to A GROUP OF FRIENDS that happen to have a thing they need to accomplish. Super Troopers is a riff on the sketch film, a grown-up version of the Doug Kenney/National Lampoon films from the ’70s and ’80s built around fully fleshed out comedic set pieces within the framework of a “Rag tag bunch” narrative.

The film is ostensibly about merry prankster highway patrolmen who have the same subversive “fuck it” mentality that the Delta Tau Chi house brought to the button up world of college frats in the early ’60s. Every beat of the ten minute opener is pitch perfect, from the charismatic lead Jay Chandrasekhar and the rookie trooper fucking with dopers driving under the influence, to “Rabbit,” in disguise, violating a multitude of traffic laws in order to lure the troopers to a bar for shots they can’t take. The crescendo comes when Rabbit hijacks the patrol car, stoners in tow and begins doing donuts in the dirt strewn parking lot outside the bar.

Super Troopers doesn’t break new ground so much as it paves it. It took the threads left dangling by Animal House, Caddyshack, Revenge of the Nerds, the films of Cheech and Chong, and Half Baked, and synthesized them into a dorm room classic. The comedy comes from a series of pranks as the Troopers fuck with each other (mostly Farva) and the unsuspecting public, taught to see their uniform and badge as authority, and completely confused and disoriented by their misuse of that institution. It’s the sort of abuse we might indulge in if we were to suddenly find ourselves in patrol cars with a stunning lack of concern for consequence.

But Super Troopers works best in the precinct. Farva is crucial as the straw that stirs the drink, and he’s a universal out of step try hard in any friend group. It works because it’s an absurdly plotted but ultimately believable fuck around and hang out movie with a group of friends.

23. Idiocracy (2006) – “President Camacho”

Mike Judge is one of two artists we’ll encounter on this list twice. In this case, it’s for his profound piece of unfortunate soothsaying. I could be wrong in my belief that this was a novel concept at the time. There are shades of H.G. Wells, Aldous Huxley, Terry Gilliam, Philip K. Dick, and David Foster Wallace in his construction of a very dark and profoundly stupid American Empire in 2505. But most speculative science fiction predicted a future that was evolved, or a cruelly fascist but effective fascist future. Judge’s misanthropic modern bent predicted how celebrity and technology conspire to infantilize us and melt our brains. While much of his predictions have come to fruition, Judge may have over shot his mark. He predicted a dystopia 500 years away, we saw his most radical prediction made flesh in November 2016.

The movie’s most frightening and accurate construction is a very game young Terry Crews as President Camacho, the world’s greatest wrestler and stickman. He’s a megalomaniac monorail salesman. He presides over a statehouse that looks like a cross between a NASCAR rally and Webster Hall. His constituency is a society of malignant brain dead monsters.

Of the 25 movies on this list and the dozens of others name checked, Idiocracy is the worst. It was strung together with spit, duct tape, and voice over narration, suppressed by 20th Century Fox and today you can see why. It’s a mean-spirited, half baked comedy less interested in story, construction, or jokes than it is with its ideas. But man, it is bursting from the seams with ideas and it’s a testament to Judge’s satirical comedic mind. In Idiocracy, human stupidity is paint on a palate and Judge is Picasso. He reaches levels of disdain Larry David and the Coen Brothers would be offended by. He’s famous for lampooning the suburbs, the workplace and the tech industry, but when he took a brief foray into the world of science fiction prognosticating, he displayed the same incisive inventiveness and inhuman human understanding that makes his critiques so devastating.

22. Office Space (1999) – “Michael Bolton”

Packed with great ideas and the kind of instant classic earworm bits you need to make a cult dorm room classic, Office Space is a much better considered and executed film than Idiocracy. It’s still ruthless in its handling of bureaucratic American stupidity but offers us a non-conformist actually likeable everyman to get behind. For me, the lasting legacy of the film as it pertains to iconic jokes is one of its simplest, and it’s all in the naming of a bit player.

Michael Bolton has become a much admired and knocked off device in which a character in a movie happens to share a regrettable government name with an infamous pop culture figure. Before “no talent ass clown” Michael Bolton was dusted off and reclaimed as a humorous piece of nostalgic pop ephemera, the joke was it would suck to share a name with him.

Michael Bolton was a perfectly random reference at the time, about five years out of his adult contemporary stardom as it began to dawn on us how truly strange the ’90s were. We’ve discussed Pynchon and Wallace, how they would name their characters after absurd, self aware, representative traits. Judge stumbled onto something else. Like Pynchon, Bolton’s name is a writer naming his character with intentionality. It’s something created in fiction, the basic artifice of naming your characters, but it’s absurd, embarrassing and random enough to have definitely occurred in real life.

21. 30 Rock (2008) – “MILF Island”

Tina Fey’s hyper-caffeinated immaculate joke machine was a Rube Goldberg device, and the gears may have never been oiled better than they were for season 2’s “Milf Island”. The episode is a stand in for all the ways the show was groundbreaking. Fey made a show about a writer’s room operate like a writer’s room with its myriad of voices it internalized immediately to perfection.

In the episode, the show “MILF Island” that the writer’s are obsessed with is a mini SNL sketch, a Survivor for hot moms delivered in the patois of mid-aughts exploitative misogyny (perfectly delivered by Rob Huebel in the tradition of celebrities being their best comedic selves with their limited 30 Rock cameos).

Consider all the levels “MILF Island” operates on as a device: It’s a perfect send up of modern reality shows, with a completely insane premise that was filmed and presented by 30 Rock with loving detail. It’s a wall for Fey’s Liz Lemon to bang her head against in her role as the cat lady, den mother, pseudo-intellectual showrunner for TGS putting her in opposition with the rest of a writer’s room that is completely obsessed with the show. It becomes a road map for the episode, as an unattributed damaging quote in the New York Post sets up an elimination style contest, forcing the cast to resort to survivalist reality show ruthlessness and alliance building to find the offender and avoid the dreaded pink slip from Jack Donoaghy.

Within the confines of this classic whodunit sitcom premise there are all the familiar joys of a workplace comedy: Jack and Liz play their classic cat vs. mouse, Machiavelli vs. Pauline Kael, commerce vs. art around who is responsible for the quote, the merits of MILF Island, and whether Liz will develop a sitcom for the show’s Omarosa. Frank is an overgrown horny teenager, Lutz is a “fat pervert loser,” Pete is a sad dad yutz with the Homer Simpsonish premise of a hand caught in the vending machine throughout the episode, and Kenneth is the earnest farmboy (“Apple faced goon”). We don’t get peak Tracy or any Jenna but there are epic levels of intricate Seinfeldian plotting, hanging out with our not quite characters delivering some of the most perfect sitcom jokes ever written and delivered at a staccato pace.

The episode brilliantly translates the heightened drama of reality television to the mundanity of an office, commenting on reality show absurdity while acknowledging the base pleasure of human nature laid bare in safe confines for our entertainment. It’s chock full of pop culture reference, fully realized inventions like the unreal reality show, the gross sounding candy “Soy Joy,” and Jack’s fake traumatic backstory as a child stutterer, punctuated with perfectly worded insult humor. Fey has done a lot for Post-Modern comedy. She was arguably SNL’s greatest head writer, perfected the High School comedy of manners with Mean Girls, and even though her Amy Pohler team up movies suck, continues to make slightly less great television with The Unbreakable Kimmy Schmidt and Good News. But it was 30 Rock that will live as her magnum opus. She simultaneously perfected and broke the sitcom by subverting its every convention while adhering to all the things we love about it.

20. Youtube (2010) – “BED INTRUDER SONG!!!”

It’s unfair that the joke/masterwork/concepts that precede this one are career peak, genre-redefining moments of genius and meticulous construction and this decidedly is not. But there are certain jokes on this list that rise due to their import and sometimes incidental yet important place in culture. Huntsville, Alabama native Antoine Dodson was understandably distressed and animated in his response to an attempted rape of his sister and that distress was caught on tape by WAFF-48 in a candid onsite interview. That video was quickly posted to Youtube, a five year old video streaming site that was taking on an increasing market share of our time and attention in 2010.

The producers The Gregory Brothers chopped up Dodson’s interview, set it to music, and using Auto-tune created a song that defined the humor of early internet 2.0. “Bed Intruder Song” is a stand in for many things. It was an early introduction to the concept of virality, perverting Warhol’s “15 minutes of fame” dictum and showing how non famous people could be isolated in 15 second increments and given the context, suddenly become as recognizable as the president. It anticipated the often mean-spirited, random, dumb brilliant humor of the internet and its potential for trolling, a precursor for the even stranger and more digestible Vine and Meme culture, the fragmenting of gag humor from its previous form as junk food into micro bites of concentrated salt, fat, and sugar.

On its own merits, “Bed Intruder Song” works because it is a perfect selection of source material and it’s catchy as hell. Dodson’s urgency and anger make for a great T-Pain styled hook and as we’ll discuss later, The Gregory Brothers seem to both know and love what makes hip hop from that period great (not to mention, a pretty impressive fluency with auto-tune), a knowledge and passion they utilize to great effect here.

Beyond its meaning, as an article of pop ephemera the song inspired what quickly became a tired joke on the internet where other would be viral producers would seek out Youtube for snippets of comedic news to remix (My personal favorite is the all-timer “Dude you have no Quran!”), and in movies in which something unfortunate would befall a character in the film, which would be caught on video, that video would go viral, then that viral video would be remixed with auto tune, and that remix would go viral. In the language of the films, this would be used to signal the character had hit a rock bottom of a very strange type of millennial internet shaming.

19. The Big Lebowski (1998) – “You’re out of your element”

The Coen Brothers deserve their own top 25 of classic jokes. Their brand of rueful dark nihilism, laughing into the void of the randomness of the universe has delivered reliable laughs in the midst of dead serious tragedies and riotous farces for over 30 years.

There’s an embarrassment of riches to choose from, so I’ll quickly run down my personal favorites: The coin flip exchange in No Country, the hoola hoop montage from The Hudsucker Proxy, Bud Grossman’s unimpressed assessment from Inside Llewyn Davis, the wood chipper from Fargo, the sonorous baritone of Fred Malamed in A Serious Man, “Would that it were so simple” from Hail Caesar, the horse trading in True Grit, almost anything Clooney does with them, but particularly his halfwit casanova in their inane Lecarre meditation on infidelity, Burn After Reading, I could go on.

Showrunner Noah Hawley has interpreted the Coen sense of black humor as a series of long, poetic, existential monologues punctuated by acts of extreme graphic violence. And that’s not wrong, but it boils down what they do to rote shtick, when there is so much nuance to their idiosyncratic comedy.

For me, their best and most important joke is a subtle one from their best and most important comedy, The Big Lebowski. The movie is full of symbolic characters embodying a spectrum of energies and philosophies: Walter Sobchak’s bullheaded kinetic aggression, Phillip Seymour Hoffman’s unfucked young Republican, The titular character’s huffy, sanctimonious, personal responsibility espousing blow hard, Smokey the Pacifist, a group of hapless kidnappers who refer to themselves as Nihilists, Julianne Moore’s new wave talky feminist sex pot, and The Dude’s bemused zen stoner Marlowe navigating it all.

And then there’s Donny. It sounds like madness to take a polished character actor like Steve Buscemi (granted, in ’98 he wasn’t quite BUSCEMI yet) and assign him a one note character like Donny, but the borderline stunt casting is very much of a piece with the rest of the Coen’s ouvre. In an All Star Game, why not play an MVP candidate as a specialist?

At first, Donny seems like little more than a good natured scratching post for Walter to claw. An immediate indicator that Sobchak is a bully and an asshole. But as the film goes on, it becomes clear that Walter kind of has a point. Donny is hopelessly and hilariously out the loop. As the stooges burn through red herrings and spin their wheels theorizing what turn is next in the convoluted maze to nowhere the Coen’s have constructed for them, Donny is always a step slow and very much besides the point.

But Theodore Donald Kerabatsos is a subtle and vital note in the film’s rhythm. He’s the third amigo in what could’ve been a quickly tiring dynamic between Walter and The Dude. The patter the three achieve is pure music, a three man weave fans of the classic comedies the film is steeped in will recognize immediately. He’s also heightened and bizarre in a mundane way, not the Coen’s bigger showy weirdness it’s so easy to gravitate towards and point to as evidence of their comedic brilliance, but a guy who plays between the bounces and rewards multiple viewings.

The Coen’s brilliant architecture lays concentric rings of reference on top of each other within genre spheres of competing influence in a random, deeply silly universe. Any character, twist of fate or line of dialogue could mean nothing or everything. It opens up their work to infinitely watchable rewatches and Room 237 levels of study and theorizing. The Coen’s land where they land on this list because of a relatively small footprint.

While there are specific filmmakers who are deeply indebted to them (I’ve always felt the humor in the work of Paul Thomas Anderson and more recently, Ruben Ostlund was particularly Coensian) and there are notes of smart-weird comedy in the mainstream they have wrought, their viewpoint is too specific and hard to replicate to see much of their influence outside their own masterful body of work (I’ve heard it argued that the trend of absurdist escalation extends from their farces. I disagree). But you couldn’t justify this list without them.

18. Inglorious Basterds (2009) – “Killing Hitler”

Tarantino dropped a suite of historical dramas after he had his fill of straightforward genre. This was his first, and most ambitious. Of course, the fingerprints of genre were all over these films and that is apparent from the musical choices to the pulp that is this intensely undignified Holocaust “Drama.” There are fantastic set pieces in this series of vignettes barely held together as a film, but the most radical and indelible moment in the film comes at its conclusion.

The film sets us up for the ultimate failure of Brad Pitt and his band of pissed off Jewish brothers avenging the Holocaust one scalp at a time with a climactic raid on Hitler’s balcony box, Valkyrie style. But something funny happens on the way to yet another sad conclusion of a bunch of well meaning Americans or Europeans trying to stop the ultimate big bad in another WWII flick: They actually pull it off. With the walls closing in on the Basterds they manage to shoot their way into Hitler’s box and proceed to riddle him with a comically excessive hail of bullets. A still shot lingers on Hitler’s corpse dancing with the impact of every shell.

Tarantino shoots the scene as the finale in a meaty piece of midnight pulp. There are close ups on an intense Eli Roth satisfying the rage of every Jew born in the twentieth century as he plays out our cathartic fever dream. Tarantino’s movie addled brain looked at one of the great atrocities in human history and where others saw divine sadness he found a great revenge flick (He would give slavery the same treatment three years later with Django Unchained). The execution’s one of the few jaw dropping hilarious moments you get from movies in a lifetime. I personally remember the sense of wonder I had in the theater as I looked up at Hitler’s bullet riddled corpse for the first time and thought, “You can DO that?”

17. Atlanta (2016-Present) – “‘With Tail Between Legs,”Juneteenth””

Atlanta owes Louie a great debt. It took Louie’s anarchist structure and spirit and inserted into a very thoughtful prolonged conversation about race, class, and privilege. Atlanta loves flouting rules and playing with your expectations, using absurdity and surrealism to make deep, gutting points about how absurd and surreal it is to be black and struggling in America. The show mixes this non-linear chaos with moments of shocking violence and stirring emotion and the result is an audience that never quite knows where up is or what can be trusted. But it’s always engaged and on its toes for that very reason.

“Juneteenth” is its best episode to date. It’s probably the closest the show comes to on the nose, “MESSAGE” satire, but the satire is so expertly executed it’s nearly impossible to find fault with. It’s mostly a bottle episode, with that bottle being a suburban nightmare mansion where you might expect a Kubrick sex party. Instead, there’s a Juneteenth party being held by Atlanta’s black upper crust, with one notable exception. The master of the house is a hilariously woke white optometrist named Craig (a perfect job and a perfect name). He’s married to a bougie black woman named Monique.

Guest director Janicza Bravo is no stranger to discomfort and failure (In her work, the under seen and under appreciated Lemon, and presumably in her life married to the cringe comic Brett Gelman) which she ratchets up excruciatingly here. There’s some tonal dissonance in the scenes where Monique lays her cards on the table as a naked, unapologetic materialist and Craig shows cartoonish levels of unawareness. Atlanta is a show that rarely calls things by their names and hates exposition, so there may be some that resent holding this episode up as the series exemplar because it’s the most obvious, which is fair.

But it so precisely hammers the themes at the show’s roots and is its most hilarious and moving episode. Since this is a list of important jokes my standout would be the imagined, “With Tail Between Legs,” about two gangbangers holding a pregnant teen, a pastor, and a drug dealer hostage in a strip club during Hurricane Katrina. It’s related to Glover’s Earn and his off again, on again baby mother Van by the play’s author, a wide eyed self serious woke woman taken to the woodshed for the same kind of lack of awareness and heightened absurdity Craig displays.

If Atlanta was just surrealist racial satire it could be no better than a live action Boondocks, using its twenty minutes a week as a platform to roast race and culture in the most obvious and absurd terms, but there’s real heart to the episode and the show in its relationship dynamics. “Juneteenth” has no B or C plots, it is an exploration of Earn and Van’s relationship, why it doesn’t work and why they keep doing it anyways. What’s remarkable is that the relationship is touching and even relatable, within the confines of the cartoonish house party. With moments like “Juneteenth,” Atlanta has found comedy in the millennial politics of representation and woke Twitter outrage. Though it’s first through this particular door, it’s incisive with a scalpel rather than an axe.

16. CB4 (1993) – “Sweat From my Balls”

CB4 opens to Slick Rick and Doug E. Fresh’s classic, “The Show” and a tracking shot bouncing around a room full of ephemera lovingly documenting the origins of hip hop. What follows is a crucifixion: Chris Rock and Nelson George take a satirical lens to gangsta rap and criticize the notion of authenticity in the music. The movie itself can be a little preachy and sanctimonious, but the opening is fitting. Even as its creators take rap to task, you can tell they really love it.

“Weird Al” Yankovic is the Van Gogh of the parody song, but he trades on a goofball juvenile humor that takes some of the sting off his parody by often making himself the butt of the joke. He also is simply remixing, taking the beat and cadence and inserting puns and a dumb theme. With CB4, Rock and his collaborators were onto something new: A “parody” that takes liberties with its source material. Rather than just changing “Bad” to “Fat,” they made their own pitched, straight faced versions of the songs and music they had their sites focused on.

With “Straight Outta Locash” and “Sweat From My Balls” CB4 displays an understanding of the exact mechanics of its musical genre in order to roast it. Twenty years later, Lonely Island would show us the same thing everyone nodding their heads while laughing to “Sweat From My Balls” got at the time: You have to truly love something and get why it works before you can effectively make fun of it. Their cover of “Talk Like Sex,” an Uncle Lukeish bedroom romp that was actually made by G. Rap and Polo, is better than G. Rap’s overlong, largely hookless original. “Sweat From my Balls” has great bounce and a sophomoric, sticky hook.

“Locash” is a good sendup of “Compton,” not just with the karaoke nightmare version of the song but with its visuals, as a denim clad MC Gusto and Dead Mike walk the streets of what looks like war torn Sarajevo with a mob of goons toting assault rifles. Part of the devastation of the punch is how good and effective the parody is on its own merits, showing how easy and formulaic it can be to replicate.

15. Wayne’s World (1992) – “The Alternate Endings”

Through his work on SNL and his comedy franchises over the course of the last three decades, Mike Myers casts a long shadow on the mainstream landscape. Myers was almost the first and was definitely the best at translating SNL to the screen by taking a character and building a story around riffy, catch phrase laden vignettes that add up to a whole. Or in other words, he broke the comedy film down to a series of SNL sketches.

Myers tends towards boring and formulaic structure. He practically invented the modern comedy sequel and that isn’t really a compliment. But his freshly conceived comedy was radical. He made his watercooler impression of his boss at 30 Rock into a legitimate Bond villain. The Austin Powers series was a referendum on Sean Connery and Roger Moore’s campy spy shlock. But his most radical joke was one of his first on screen.

Wayne’s World was better than it had any right to be, built out of five minute sketches as goofy-sarcastic but saccharine, aggressively white rockist twenty somethings riff out of a basement in Aurora, Illinois. But within that framework, Myers packed a shit ton of ideas. The out of nowhere Queen sing-a-long is iconic but there’s also the sub-title jokes, ranting about uncompromising authenticity as they make sport out of grotesque product placement; it’s a movie full of wall breaking surreality that brought the audience in on the absurd fun.

The most formally daring moment is the conclusion when the movie cycles through an assortment of possible endings, basically laughing at the idea that anyone could be invested in the stakes of the narrative and laying bare the fact that you just watched an hour and a half of jokes by throwing away the climax. Over the course of final four minutes, the film shows us a darkest timeline ending, a Scooby Doo scenario recreating the set-up of the original ending and Rob Lowe is unmasked as Old Man Withers, and then finally delivering the expected, standard “Mega Happy Ending.”

They pay off the narrative and mash all the pleasure buttons with an equally over the top PSA-like finale in which both Wayne and Garth get their girls, and every major character addresses the camera reporting something they’ve learned. Then Myers and Carvey break and the whole cast begins goofing off as we fade to black, not unlike the end of an SNL episode.

The only reference I could come up with here was 1985’s Clue movie in which alternate endings were sent to different theaters, and later were all played together when the movie would run on Comedy Central ad infinitum in the ’90s. What makes the Wayne’s World finale unique is how the endings are all shaded differently, but the intense, goofy absurdity is static. Both the dark and happy endings are ramped up to extreme levels that lay bare how silly the notion of a satisfying or depressing conclusion can be, and the Scooby Doo ending is sandwiched for good measure by referencing an actual cartoon. This notion of steroidal, heightened climax will be revisited later in the list, and was a major facet of Werner Herzog’s Bad Lieutenant 2: Port of Call New Orleans, an absolutely incredible film whose over the top conclusion just missed my list.

14. Louie (2012) – “Louie’s Black Wife, ‘Miami'”

We may never hear from Louie C.K. again, and maybe that’s okay. Besides being a tortured guy with a difficult relationship with women and sexuality, his comedy came to embody the worst and least interesting form of talky, introspective, and self satisfied male liberalism (He would have voted for Obama a third time if he could’ve); the kind of self evident, self righteous coastal common sense that motivated aggrieved poor white people to put Donald Trump in the White House.

But with his resume, it would be disingenuous to leave him off this list. His iconic visit to the Conan O’Brien show where he unleashed “Everything is Incredible and Nobody’s Happy,” a searing, everyman rant speaking truth to power basically relaunched his stand up career. He was also a writer on The Dana Carvey Show, The Chris Rock Show, and the writer/director of Pootie Tang. In terms of comedic language, the expansion of boundaries, and the reconsideration of what is possible, it’s his show on FX—a subversive nonlinear long form exploration of his neurosis and self loathing—that made the largest impact.

Louie injected Lynchian fever dream logic into the 30 minute comedy format. He wiped his ass with narrative coherence, and while Seinfeld made “No hugging, no learning” famous, Louie took the subversion a step further and boldly proclaimed “No (real) story.” Instead, Louie is a tonal achievement of style, a surrealist melding of free associative ideas within the structure of “Just how real is this?” line blurring autobiography, goofball slapstick, and layers upon layers of contradictory meaning.

My recollection of a first and lasting “Oh Shit” moment was the (re)-introduction of Louie’s wife Janet in Season 3. We had become loosely acquainted with a character playing the mother of Louie’s children. She’s white, as you would expect given Louie’s complexion and his aggressively white daughters featured prominently on the show. But over the course of several episodes in Season 3, she turns out to be black, with no warning or explanation. Seasons later, there would be a half assed explanation that Janet was biracial but it’s entirely besides the point. In a flashback episode the girl playing Janet is white, and story telling decisions like Janet’s unexplained ethnicity are the rule for the show, not the exception.

The obvious and most important disciple of Louie is the aforementioned Atlanta, a show that works in the same non-linear, dreamlike fashion, turning its eye outward on race and class rather than inward on a sad Mexican-Irishman and his self hatred to much greater effect. But there’s no arguing with the formative thrill, the high wire act of early Louie as it traded in shock, surprise, and subversion, skillfully breaking rules right and left and changing our understanding of how a half hour comedy can operate.

13. Don’t be a Menace to South Central While Drinking Your Juice in the Hood (1996) – “MESSAGE!”

Don’t Be A Menace, the very best of the Wayan’s genre critiques, is a feature length instance of searing criticism. The Wayans already had roots in spoofy satire, with Keenan Ivory’s I’m Gonna Git You Sucka taking ’70s Blaxploitation to task and his In Living Color casting a wide net on culture—terrain that lily white sketch shows like SNL had covered but people of color were rarely included in. Pull back the lense a little and their are roots for Keenan’s style in Robert Townsend’s groundbreaking show business critique Hollywood Shuffle, as well as the madcap spoof classic Airplane!

Don’t Be A Menace showed the true adaptability of the format the Airplane! team and the Wayans had cooked up independently and together. It created a cottage industry, a platform for actors of color to establish themselves in the mainstream, and a cultural touchstone for young, smart movie goers of color who were sick of being “catered” to by a cynical Hollywood Industrial Complex who took their dollars for granted and unloaded B shlock on them. But more importantly, it courageously spoke up against the lazier narrative devices ghetto dramas leaned on. It intelligently, incisively, and hilariously insisted black filmmakers covering black issues in film needed to do better.

At the time, a second wave of a kind of Blaxploitation film was en vogue. Boyz n the Hood was groundbreaking. An urgent issue film that was a call to arms for ghettos all over America, giving voice and a perspective to a tragedy largely demonized in the press and film. It birthed an entire genre: The Hood flick. These movies launched careers, served as showcases for great and important talent both behind and in front of the camera that changed the film industry forever, and in spots were good to great. But they also suffered from formula and convention. Lazy plotting and character work, gimmicky camera tricks, predictable music cues, and soapy melodrama. It was ripe for parody, but extremely problematic for the largely white critical hoard to take to task. Keenan Ivory Wayans wasn’t a film critic, but he collaborated with the two youngest brothers in his ten child family to make a work of real lasting criticism that changed spoof flicks.

Don’t be a Menace takes on many of the very dark and serious themes of its source materials: disposability of impoverished black youth, the broken black home, privilege, impressionability of youth through violent culture, the death cycle of black on black revenge tribalism, these conventions were all knee-capped by delivering them in their worst forms with a straight face, nakedly laying out themes with intentionally stilted dialogue and grade school symbolism salted with absurdist slapstick.

It’s a film that slaughters all sacred cows. It would be easy to interpret as racist with its cartoon glove treatment of gangstas and welfare queens, but it’s smarter and funnier than that. There’s Preach, a genuinely hilarious invention, a positive militant brother who is also ignorant and hood, or Toothpick, the guy who can’t adjust to life outside the penitentiary, a profiling Korean grocer, an overly animated huckster Baptist Priest, and an evil white man who runs around creating mayhem and sewing evil. One cutaway scene is slow mo beauties of what looks like a crack cook up and winds up being a tiered decorative cake, a brilliantly subversive commentary on the “Have their cake and eat it too” demonization and glorification of the drug trade many of these movies exploited. It’s a film that trades in stereotype but with a purpose. To lay bare the lack of nuance or development in these archetypes on film.

There’s also a lot of fourth wall breaking. Keenan himself plays a mailman who pops his head in sporadically to poke fun at the didactic, on the nose moralizing early ’90s hood flicks were guilty of far too often. Keenan’s occasional drop in punctuation is an ultimatum to screenwriters and filmmakers who would come after: Stop holding your audience by the hand, this messaging is reductive and insulting.

Perhaps it was a trend dying out, maybe there were diminishing returns at the box office making it harder to get financing dollars or maybe this movie was just that effective, but in the wake of Don’t be a Menace, the hood flick largely went away. In 2000, Keenan and his youngest brothers would return with Scary Movie, which along with the meta and referential Scream franchise, was a similar call to arms for formulaic horror films, often aimed at communities of color. Twenty years later, genre is king. Horror regularly cleans up at the box office, and just this year a scary movie about race made by a smart nerd of color was nominated for an Oscar. The intelligence and thoughtfulness of these movies are a world away from the horror smart nerds of color were subjected to throughout the ’90s. Maybe the sudden maturity of the genre was a coincidence, or maybe Hollywood finally got the message.

12. Swingers (1996) – “The Voicemails”

Swingers is an antiquated film in many ways. The clothes, the haircuts, the slang, the sexual politics, the nightlife. So it’s fitting that its resonant and impactful joke revolves around an extinct piece of technology. But before we get into that let’s explore the ways in which the film’s perspective was very much ahead of its time.

My hazy recollection of Swingers is as a small ’90s indie comedy about a guy getting back on his feet after being devastated by a relationship. Cheered on by his friend group, Jon Favreau’s Mikey regains his confidence and finds the courage to venture back into the world of dating and relationships. Much of the humor is derived from Mikey’s false starts and mishaps, and the outsized personality of his friend, cheerleader, and asshole comic relief, Trent.

Maybe this has nothing to do with writer Favreau or Director Doug Liman’s intention, but watching Swingers in 2018 is a very different experience. The film can be viewed as a dissection of toxic, fragile masculinity with Vince Vaughn’s sentient throbbing erection Trent as transparent insecurity posing as the id and Mikey as transparent insecurity unable to pose as anything else.

Mikey is positioned as the “nice guy,” licking his wounds but morally upstanding and respectful of women while Trent is the manipulative and callous player trying to woo his friend to the darkside because he has so much “potential.” Over the course of the film, the protagonists are both unmasked as awful, with Mikey unaware that his narrative of the relationship he’s recovering from is dishonest to both parties and in many ways his relationship with women is just as fraught and fucked up as Trent’s.

But the revelatory scene in the film comes after Mikey is coached up by Trent and scores a number off a girl named Nicky in a bar. There’s a pretty hilarious altercation with their friend—a toxic male with a gun—in the parking lot after the bar. The friend tells Mikey that he may have gotten a number but he’s just going to fuck it up because he’s a loser and that’s just what he does.

The expectation might be for Mikey to shut this jerk up and prove him wrong, but Mikey is sent down a self hating shame spiral. He runs away from the altercation like a wounded animal and heads home, where he proceeds to leave a series of hilariously uncomfortable voice mails on the poor and unsuspecting Nicky’s answering machine.

Liman is masterful shooting this, leaving the camera on Mikey in a long, excruciating shot as he digs his hole deeper and deeper. At one point, Mikey runs away from the phone as if it was lethal, which it is, but Liman leaves his camera lingering on the phone in a shot that reminds me of the airplane bottle of Ketel calling to Denzel Washington in Flight. There’s a terror and dread in watching the inanimate object of desire the addict will eventually return to, which of course Mikey does.

We use the word cringe comedy a lot these days. Shows like The Office and Ricky Gervais’ greater body of work trade on it; the unbearable and awful person in question behaving badly and receiving their comeuppance. It’s hard to watch and it’s hard to look away. The first time I remember the sensation of watching something so squirmy and uncomfortable I wanted to shut off the television or jump through it and beg the protagonist to stop for the love of God was here, as Mikey fucked up his first real chance for “redemption” in the film’s eyes. It’s still what I come back to when I think about cringe comedy.

Mikey continues to fumble through a series of awful messages on the answering machine, rehashing his broken romantic history with his ex, coming off needy, insecure, and accusatory, having a whole relationship, ending it, and apologizing for it with an answering machine. Eventually Nicky cuts him off, picking up the phone and asking him to never call her again. She’s right.

11. Friday (1995) – “Ezell”

22 year old Craig Jones wakes up hungry. But as his friend Smoky later observes, his house is incomplete. Kool Aid with no sugar, peanut butter with no jelly, ham with no burger, cereal with no milk. He’s saved, we’re lead to believe, by his mom who is making eggs, bacon, sausage, pancakes and some left over pork chops. Craig is elated, only to discover she’s made breakfast for herself and he’ll have to make do with with cereal and tap water.

It’s through this simple and humble lesson that we’re introduced to the logic of Ice Cube, DJ Pooh, and F. Gary Gray’s classic Friday. It presented a family unit and community unrecognizable to many, in their lives and as we’ve seen them represented on television and in film. Craig is a member of a family that is loving, but it’s a tough love. They support each other through thick and thin, but it’s a demanding and impatient support.

Through breakfast and through many other moments, his family and the film are both urging Craig to grow up. As a black man in an impoverished community, life isn’t going to provide milk for your cereal. Your manager won’t care if it’s your day off, Big Worm is going to want his money and there’s a Deebo waiting around every corner…not to mention the cops. Self sufficiency and resilience is the only way you’re going to survive an oppressive system with a rooting interest in seeing you fail.

Friday was revolutionary, not just in the way it conveyed this family unit that wasn’t necessarily familiar to mainstream white America, but in how it presented the tragedy of everyday poverty rendered comic. There is sadness in how little a poor black kid in Compton can take for granted, but it’s also great when you get a beep from Kim or the Lakers beat the Supersonics. In the same way, it was able to present Ezel, the protagonist in a sad story we’ll never see, as a kind of funny piece of ephemera in Craig’s community. A character providing comic relief on his fucked up Sesame Street.

Before Friday, the drug addict was almost exclusively presented as a cautionary tale, a tragic figure society had turned a blind eye towards, a caricature Nancy Reagan would look for in her closet and under her bed. Mario Van Peebles’ New Jack City is admirable in its desire to humanize the junkie in the form of Chris Rock’s Pookie, but it only does so in the starkest, most condescending and melodramatic terms. Pookie is a lost soul who wants to get better but can’t, he needs a paternal figure in the form of Ice-T, Judd Nelsonm, and The State to get him into rehab and back on his feet. There’s also the sad/unintentionally funny “cheeseburger” scene from Menace where a nameless crackhead gets popped by O-Dog for offering to suck his dick in a desperate moment for a hit.

For me, the absolute nadir of this sort of preachy moralizing comes from Spike Lee’s God awful adaptation of Richard Price’s Clockers in 1995. The great Thomas Jefferson Byrd, a reliable Lee ensemble player, is trapped in the role of Erroll, a heroin addict with AIDS forced to deliver an after school special in miniature scored to an acoustic version of Seal’s “Crazy.”

AJ Johnson offered us another vision of the drug addict as Ezel, the crackhead in whom necessity creates a low stakes genius. Ezel is walking need, constant in his negotiation and scheming but from the perspective of Smokey and Craig he’s a pest at worst and humorous texture at best. He’s simply a part of the fabric in their community, his representation could be looked at as mean spirited or irresponsible but it’s above all things honest from Craig’s POV. Gray, Pooh, and Cube’s decision to relate the neighborhood crackhead as such could be viewed through a certain lens as an act of integrity and courage.

There were antecedents for Smokey. Notably (to the best of my knowledge) Pryor’s wino and Chris Rock’s increasingly desperate negotiator in I’m Gonna Git You Sucka which he’d reprise occasionally for In Living Color and later there’d be characterizations played for straight laughs like Dave Chapelle’s intentionally cartoonish Tyrone Biggums, but Ezel is on this list, among other things, for context.

Friday took what was at the time grist for an alarmist mill and related its heart, the necessary normalcy of everyday life in what was understood in white America as a tragic nightmare. While there are elements of tragedy and nightmare in Friday, it is a deeply empathic and humanistic movie. The “evil” local drug dealer has great taste in music, curlers, and an ice cream truck, but is also deeply principled, the eses are practical jokers, and in his own way the crackhead is charismatic, resourceful, and funny.

10. Friends (1998) – “‘The One With The Embryos,’ The Trivia Contest”

It’s a familiar sitcom premise: Two sub-sections of a larger friend group are competing against each other for bragging rights (the stakes are ratcheted to comic lengths—stewardship of the more desirable West Village apartment). What changes is the resolution. No absurd feats of talent or skill, a simple trivia contest challenging two friend couplets to see which knows the other better. It’s simple but radical.

On previous shows like Cheers, much of the relationship building happens on screen. Even when a prior relationship is explained or alluded to, rarely will the specificity of a personal relationship dynamic be something that’s explained with shorthand. Sometimes there are callbacks to events of older episodes, but rarely will a whole history be suggested off screen.
The trivia contest is a perfect comedic scenario, endearing in what we learn about characters via previously unknown trivia answers (i.e. Chandler is afraid of Riverdance), endearing in that the characters are so deeply familiar with one another, endearing in Ross’ ability to generate the questions and the seriousness in which he assumes his hosting duties, endearing in its resolution.

After all, the impossibly intimate minutiae has been covered. The fate of the contest rests on Monica and Rachel’s ability to say what Chandler—the boring suit you love to hang out with but don’t particularly care what he’s doing in that suit—does for a living. But most importantly, it deepens the intimacy and bonds between characters to levels that are realistically uncomfortable (i.e., knowing what time of the month a friend typically menstruates).

Many of the jokes on this list rest on the lived in bonds of group dynamics and friendships that have to find ways of being conveyed through shorthand, without the benefit of thousands of hours log time individuals get off screen IRL. This is a great and important example of how to accomplish that.

9. Chasing Amy (1997) – “The Wrist”

Kevin Smith did for listless New Jersey 20-somethings what Quentin Tarantino did for hitmen and drug dealers. He had the same indie brand of chatty neuroses that breathed life into his assortment of Garden State misfits. But along the way he changed the way we think, talk, and laugh about sex on film with Chasing Amy.

The movie is a little clunky in its premise. It’s a romantic comedy on its face with the great Joey Lauren Adams as Ben Affleck’s love interest, but as Adams says facetiously, “But get this, she’s gay!” I would imagine the idea of a film discussing sexuality as a rom com stumbling block would be offensive to many members of the LBGT community (However common the practice of sexual fluidity may be), but if you can get past that admittedly large detraction (that to its credit, the film acknowledges), there’s a lot of interesting and important ground mined here.

The joke in question comes as Affleck’s Holden (BARF) goes on a morning after friend date with Adams’ Alyssa. Alyssa struggles to dismantle Holden’s straight male definition of virginity and how it’s lost. As they very graphically get down into what it means to lose one’s virginity they are also disposing of the conventional definitions of sex, love, and sexuality. Alyssa simulates fisting for Holden on a New Jersey swingset, and manages to expand his mind. Suffice to say this was not the sort of conversation commonly overheard in romantic comedies at the time.

The nature of their conversation is something like a National Geographic special where a sociologist explains the rituals of an obscure ancient tribe to an ignorant audience. This will be problematic to a number of viewers but it also ends up being the point of the movie. Holden and Jason Lee’s Banky are two sexually confused and repressed young men. Much like Swingers, the movie sets our expectations with Holden as the progressive nice guy and Banky as the offensive, outrageous beta clinging to outdated sexual orthodoxy. But it turns out they’re both morons as the real stumbling block for Holden and Alyssa’s relationship isn’t her sexuality, but her checkered sexual history and Holden’s inability to come to terms with it in his toxic male lizard brain.

The film is a frank discussion of gender and sexuality way ahead of its time. It subverted the sexual morality and protagonist-overcoming-an-obstacle structure that had become calcified in the romantic comedy. It detonated the romantic comedy love interest in ways obvious through sexuality, and not obvious through challenging our image of the chaste, ideal feminine object on a pedestal. Chasing Amy was the sexual maturity of romantic comedy. It said, this is what sex is really like. The introductory, exploratory, unbearably ’90s sexual politics of the movie haven’t aged well through a woke 2018 lens, but in 1997 it was the discovery of fire in a dark age.

8. Step Brothers (2008) – “Baby Aspirin”

Adam Mckay and Will Ferrell probably take the award for producing the most great jokes on this list. They’ve made six movies together, and they’re pretty much all high volume shooting joke cannons that land at unprecedented percentages. Some of this belongs to Ferrell alone. He was and still occasionally is a once in a generation comedic talent, a guy who is genetically gifted as someone who can make you laugh for no reason at all. Throw in his incredible level of commitment, both physically and emotionally, to character and bit and you have a first ballot hall of famer.

But it’s his union with Mckay that melded great talent with great system. The Mckay/Ferrell oeuvre owes a debt to the Myers comedies of the ’90s. Like Wayne’s World and Austin Powers, they took sketch and consecrated it in film. Like Apatow, their innovation was literally throwing out the script. Taking a bunch of comedians and improv products, inserting a premise and letting the camera roll. In doing this, they took the unplannable, unscriptable surprise of in moment, unedited comedic inspiration and worked it into bits. The product was as weird and bizarre and hilarious as the unbridled, unadulterated human imagination.

They also were radical in their complete and utter disregard for story. There are other films on this list that toed the line of disregard for plotting and stakes, but Mckay and Ferrell gleefully dumped kerosene on the notion and shot it with a blowtorch. Sure, they adhere to the classic beats of sports films, buddy cop flicks, underdog narratives, and redemption tales, but at every juncture they’re flouting and spoofing the ideas of these beats at levels that are downright Wayansian. Want proof? Consider the Catalina Wine Mixer.

Step Brothers is something of an anomaly in the Ferrell-Mckay filmography. Every other entry has a construct it’s playing with, a character it’s riffing on, an idea it’s getting to the heart of. There isn’t much in the way of predecessors for what Step Brothers is, what it’s about, how it works or what it means. With little rhyme or reason, two sixty somethings fall in love and marry, they happen to have two live in forty something sons who have to adjust to new lives. That’s about it. But within that flimsy premise, Mckay and Ferrell made one of the funniest and deranged movies on this list, possibly ever.

The film hums at its own bizarre frequency. If you squint in a certain light it can be seen as part of director Adam Mckay’s scholarly career spanning interrogation of willful idiocy in Bush’s America in the form of two developmentally arrested spoiled fail sons (The film opens with an H.W. quote), but that’s much like the plot in a Coen Brothers farce. The real point is madcap stupidity for its own sake, to watch two wildly talented, perfectly calibrated comedians at their apexes go at one another within the confines of a series of loosely connected improv sketches.

The film kind of works like a Romantic comedy? There’s the unlikely coupling of two people perfect for each other but unable to recognize this simple truth. They finally fall hard, there’s a sudden traumatic event splitting them apart, then just when it seems like it’s over, a Parent Trap-y miraculous resolution. But man, what a resolution.

Adam Mckay and Will Ferrell often engaged in nuclear brinkmanship throughout their fruitful partnership. There are other examples of this idea of ultimate commitment: “The Anchor Fight” and “The Jazz Flute” in Anchorman, “Baby Jesus” from Talladega Nights, even “Sweet Child of Mine” or “Sleepwalking” from this very movie, but if you want to see escalation go from insane to absurd to cartoonish to believable and back through this gamut several times over, the climax of Step Brothers, the Catalina Wine Mixer, takes the cake.

7. Knocked Up (2007) – “Just watch your back, Serpico”

Adam Mckay and Judd Apatow represent the Hell Hath No Fury and Lord Willin of modern bro humor (#TeamLordWillin fuck with me). Judd Apatow gets the nod on this list for the same reason I prefer Friday to Friday After Next: one is a movie that’s great because it’s funny, arguably funnier than its predecessor. The other is a great movie that is also very funny. In his commitment to rule breaking and theory, McKay makes radical and hilarious films that are nearly drained of humanity. With his disdain for story and character, he’s left with movies that are difficult to invest in. This is a somewhat subjective question of what you go to movies for, how you feel about the constraints of structure and the artifice of story, how you feel about hugging and learning. I personally like to learn and hug, and so while respecting the genius and craft of Mckay, Apatow gets the nod.

Knocked Up is a romantic comedy about a guy who accidentally gets his one night stand pregnant. It’s stripped of the affectations that have plagued romantic comedies throughout the years before because it isn’t exactly a romantic comedy. It’s raunchy like a McKay or Farrelly Brothers farce, it doesn’t spend as much time as you might expect focused on its perfectly imperfect protagonists because they are decidedly not meant for each other. It’s talky, character driven, and introspective like Woody Allen or Nora Ephron, it’s shaggy, and about thirty minutes too long. In other words, it’s a Judd Apatow film.

Much like the Ferrell and Mckay comedies, the secret to its personality and humor relies on leaving the cameras on. The off-the-cuff conversational quality of the conversations in the film come from their barely scripted natures. The humor is as unpredictable and original as, say Anchorman, but without the cartoonish, heightened, brilliant/retarded arch shit. It approximates reality, the reality of felt emotion, argument, the bull sessions and shit shooting that bonding and friendship are composed of. It’s practically New Wave. But unlike New Wave these are bros in the early aughts trying to get their shit together, or sisters grappling with their careers and getting old, or kids wrapping their heads around mortality for the first time, or husbands settling into middle age.

The film establishes tone and its radical mundanity with a simple bet. Martin Starr’s Martin (Interestingly, the bro roommates with the exception of Seth Rogen are the only characters in the film who keep their first names) can’t shave for a year. Martin has the literal density of a guy that has smoked himself stupid. He’s surrounded by lightning quick, riffy borscht belt Jews firing off a relentless torrent of one liners and entertaining themselves with his befuddlement.

What’s brilliant about Apatow’s process isn’t just the hits. The digs are direct, funny, raunchy and accurate, but he also leaves in the duds. At one point Jay Baruchel’s Try Hard launches into a regrettable Chewbacca impression. It’s a bad impression and a bad joke, and the inevitable result of a bunch of non-professional dudes making fun of a friend. Sometimes you’ll mine gold and in any high volume endeavor there’s some soot. The entire device of the beard contest does nothing. It doesn’t advance the plot, it doesn’t mean anything, and yet it’s the entire point of the film and Apatow’s contribution to how characters relate to one another on screen.

But it wouldn’t work if there weren’t sharp comedic minds at work. The titular joke here is casually fired off by Jason Segel, your funniest and sharpest friend. The bros practice a specific strain of insult humor cribbed from generations of standups quelling hecklers and it’s put to good use here. We establish likeability, familiarity, and intimacy with our protagonists. Apatow’s comedies, and the many good to great comedies that have grown out of his system and style, have been accurately identified as bromances. Knocked Up gets that it’s not a template rom com about a shlubby guy getting with a type A careerist. It’s a bittersweet story about a group of people who love each other growing apart. That dynamic would either be hard to understand, or hard to care about without an established language of acerbic, smart/funny jokes fleshing out and filling in the cast of characters.

6. Reservoir Dogs (1992) – “Like A Virgin”

“It’s all about a girl who dates a guy with a big dick. It’s all a metaphor for big dicks.” Those words are spoken by Mr. Brown, played by Tarantino himself while eating breakfast at a diner. The conversation and Tarantino’s explicit interpretation is funny, but that’s largely besides the point. The rest of Reservoir Dogs, while inventive in its non-linear telling, unfolds like a cross between The Killing and The Thing, a botched heist leads to whodunit recriminations, paranoia, and wanton violence. But first we spend ten minutes with the table full of hardened killers absorbing Tarantino’s interpretation of an old Madonna song. The guys leave the diner, embarking on the fateful robbery that makes up the rest of the film, but years later it’s the diner scene that stays with me.

Before Reservoir Dogs, bank robbers didn’t talk about pop songs, or air their neuroses about tipping. Hit men didn’t discuss their vacations to Amsterdam. or the merits of imaginary Hawaiian burger chains. Coked up mob wives didn’t discuss their failed pilots, Nazis didn’t rhapsodize on the merits of a strudel. These characters, often to the sides of the frames as our traditional protagonists and moral centers grappled with the themes of a given film, were little more than devices hanging around to step in and service the plot. Tarantino gave them a voice and interior life and it turns out they think about old pop music and marvel at what Big Macs are referred to in foreign countries just like us.

It was a deftly timed observation. Our culture is turning ever more inward, a vast nostalgic beast always eating and always shitting. Tarantino’s conversational flourishes, full of pop culture reference and theory increasingly sound like how we talk. If Fitzgerald is to be believed that personality was once an unbroken series of successful gestures, today we might describe it as a coherent grouping of Facebook page likes.

We don’t necessarily need to know about a teenage boy’s traumatic relationship with his father, but we can learn a lot from what movie posters hang in his room, what band t-shirts he wears, and what book he carries around. This can result in lazy writing, and it did, with hordes of Tarantino knock offs flooding movie theaters in the late ’90s and early 2000s, but it also changed the way characters speak and interact, brought some of the stupid, disposable outside world into art. The fictional world of a movie or television show suddenly became both larger, and smaller.

5. Jon Stewart on Crossfire (2004) – “Stop hurting America.”

We’ve discussed comedy as a form of critique. In the case of John Stewart and his 16 years at the helm of The Daily Show, it was an all out assault on American political discourse. It was one of the most brilliant subversive takes on stupidity in media ever waged. It failed entirely, possibly even contributing in making our partisan, over saturated media industry more sophisticated in packaging its pre conceived viewpoints, but it shaped an entire generation of political thought that is still very much a part of how we digest and discuss news.

Stewart took the helm of an afterthought talk show experiment on an also-ran deep cable network at an apt time. He got in a year of reps before the highly contested 2000 presidential election, then a year after that the towers fell, and with it in many ways, the very idea of American consensus. In January of 2002, just four months after September 11th, Fox News became the most watched cable news channel in America. It has held that distinction ever since. Fox didn’t invent news and agenda, its very founding was on the idea that the supposedly objective fair and balanced news men of the last century in “liberal leaning” basic cable news skewed left. Subject Rupert Murdoch to 23 and Me and you’ll no doubt find some of William Randolph Hearst’s yellow blood in his DNA. But never had the presentation been so naked, the facts so inessential, manipulatable to a larger story a network was telling its viewers, the one it wanted to hear about a country it wanted to believe existed, that it ever had existed.

Stewart left journalism to journalists and instead set out to expose the truth tellers by telling his own truth. That there were too many hours in a day and not enough relevant or entertaining news to fill it. That the necessity to attract advertisers was crippling the greater good of journalism meant to inform and nourish a republic. That the ship was taking on water and about to break in half.

He delivered nightly hellfire sermons from behind his desk, pre-ironic detachment. His weapons were the video montage, the self evident stupidity of his big fat targets, and his sense of decency. His sense of humor was very much in the vein of the Jewish Borscht belt before him, which he’d use to occasionally lighten the mood, but his best weapon and go to move was stunned incredulity, the bewilderment of the last sane man in a mental institution run by the inmates. His best work hits a weird kind of funny bone, not always laugh out loud and never warm. It’s part anger, part outrage, from a gatekeeper who sifts through thousands of hours of soggy newsertainment shit to confirm all your worst suspicions about the direction culture and society are headed. He’s mean, but he’s picking on bullies and hacks and from his perspective that even the hacks are their own type of threat.

His best and most iconic moment wasn’t aimed at his longtime nemesis on the right, or even on his own show. It was as a guest on CNN’s partisan, nightly news debate show, Crossfire. It was an interesting and prophetic choice in target by Stewart. The show was an early harbinger of where televised political discourse was heading. It was founded in the early ’80s on the premise of two distinct and opposite political viewpoints debating. The very format demands conflict and the inability to compromise or change minds. Political identity and perspective is fixed, permanent, and in irreconcilable difference to its opposite. Stewart correctly identified this as political hackery and this false discourse as the idea of meaningful political debate spun into irrelevancy.

Set aside much of the meat of Stewart’s argument, in which he shirks his own responsibility behind the at-the-time novel position of being a serious voice of news on Comedy Central. Stewart’s “Mad as hell” rant, completely derailing what was supposed to be a fun and chatty interview segment on a media debate show he helped cancel shocked many of us awake. By refusing to play by the basic conventions of a cable news interview structure and interrogating two partisan hacks on their own turf as to their importance and role in the slow dismantling of our democracy, Stewart laid bare the cheap disposability of the hours of programming early aughts cable news subjected us all to.

It is the finest example of his everyman, truth to power, laughing to keep from crying in the face of the dark, blood soaked machinery of empire. With his rant, Stewart created a new kind of viral moment. The owning, or public shaming of an unsuspecting target. Twelve years later, “Dunking” on someone with a retort or stream of concentrated rage has become a spectator sport on Twitter.

Much like Bunny Colvin in The Wire, it would be hard to look at where political discourse has gone and say the world is a better place than it was when Stewart began his crusade. Tucker Carlson, the very douche he spent most of his time on the show taking pot shots at, is more powerful and influential than he was when Stewart “took him down” (And the format of his show largely depends on his takedowns of fatted calves employing the same analytical sneering Stewart used against him).

Stewart left his show in 2015 and his shtick has been widely mimicked and saturated with versions of his perspective preaching to their individual choirs in the same manner as O’Reilly and Beck and Cooper and Maddow. This could be viewed as critique but it isn’t. It’s a testament to the power and resonance of Stewart’s perspective that it’s become so widely emulated. It appears no one person, or even group of people are capable of the type of change he was desperate for. The wave reached its high water mark and rolled back long ago. But Stewart changed the way we view spin, the way we challenge conventional wisdom, and political discourse itself.

4. Seinfeld (1994) – “‘The Chinese Restaurant,’ Five, Ten Minutes”

This list wouldn’t be complete without Larry David’s particular gifts. He’s made a career out of bending coincidence and circumstance around his intricately plotted universe of neurotic in-jokes. But ironically, the essence of his contributions can be found in a twenty minute episode of his best show that didn’t require a small, coincidence riddled conspiratorial universe being bent to service another of his jewel box plots. It all takes place inside the waiting area of a small Chinese restaurant in Manhattan.

We get A, B, and C non stories for all three of the players in the restaurant. Elaine is hungry. Jerry sees a woman he can’t place. George needs to use the phone. The stories are connected thematically and as usual, the subject is the existential insignificance of the individual with New York City standing in for a cold and uncaring universe. Each gets equal time and each displays another subtle shade of the neurotic Jewish New Yorker.

Jerry spends much of the wait time trying to place a mystery woman, self flagellating for lying to his uncle to cancel a dinner date, and nervous he will miss the reason for the cancellation, a theater screening of Ed Wood’s B movie classic Plan 9 From Outer Space. George needs to use the phone to try to make up with his on the outs girlfriend Tatiana, stemming from a makeout session he had to wordlessly bail on to run home and shit. But it’s Elaine, the shiksa Jewish by proxy in the way all New Yorkers become at least a quarter Jewish by proxy, whose Sisyphean despair in her quest for an eggroll takes on the operatic heights that lovers of Seinfeld will recognize as its trademark combination of patently absurd and universally relatable.

We’ve all faced the Kafka-like madness of an overlong wait for food, the opaque inhumanity of the first generation gatekeeper (The arrival of the magnanimous ball breaking regular Arthur Cohen, and the subsequent dropping of guard by the host is particularly surreal and jarring. It’s like seeing an animatronic figure come alive after dropping a quarter in the slot), and it’s Elaine’s roll as our proxy, for once not suspending disbelief and acknowledging the insanity of a Seinfeld plot that makes this episode resonate so heavily.

It’s a perfect articulation of the dark Jewish neurotic mindstate railing against age old injustice and cosmic oppression manifested in late 20th century bullshit mundanity. This is about as well as I can explain the modern Jewish predicament and how its at once specific to us and relatable to everyone. Justice and principle don’t just evaporate with accomplishment and privilege, as it pertains to a people and a nation. Just because we no longer have to wonder where our next meal is coming from, doesn’t mean it alleviates the frustration at not being able to get the meal we want at the Chinese restaurant by the theater playing a re-run of our favorite bat shit B movie classic when we want it for no discerneble reason.

It’s also just a nutty, brilliant idea for an episode of television literally no other show ever would’ve even considered attempting before 1994, then well after. Even for a show about nothing, this was an episode about NOTHING. Three of the main players with no other real support are left in a Beckett play to wring their hands and suffer with no relief or meaning to excuse or explain the suffering. And perhaps that’s why I gravitate to this episode of Seinfeld over all the others, including Larry’s PHD, Curb Your Enthusiasm, it’s at once the tamest, most formally daring and most indicative episode of either show, the most perfect formulation of the sensibility created by the mindmeld of David and Seinfeld ever produced.

3. The Chappelle Show (2003) / Bring the Pain (1996) – “Clayton Bigsby / N****s vs. Black People”

Without Dave Chappelle and Chris Rock, it would be impossible for me to even compose this list. It’s equally difficult to separate their contributions, to discuss them separately from one another. They are the Jung and Freud of modern race humor. Dave Chappelle and Chris Rock are without a doubt the two funniest, most intelligent, and most important comedians on this list. They are *only* third on this list because they are such extraordinary, singular talents that their specific contributions in total would be impossible to replicate. The way they thought and spoke about race was not.

We’ll start with Rock, because he came first. A kid from Brooklyn who grew up worshipping Eddie Murphy, Rock seemed destined for a kind of low stakes, also-ran minor black celebrity. He made very little impression in his stint on SNL, his other film and television contributions were notable but somewhat aimless. His standup was confident but clunky. The early swagger is there and you can see his tentative steps towards the full throated, mic dropping monster he’d become, but the material sucks. Seinfeld was a clear early influence, mixing observation with absurdity. A particularly blah bit about masturbating to Aunt Jemima because his mom swiped his porn mags reminds me of the Eddie Murphy bit about his pre-adolescent standup about pee and poop jokes (Actually, Eddie’s pee and poop jokes in perfect Pryor patois were much funnier).

Bring the Pain opens with a montage of formative comedy albums. His taste is impeccable: Dick Gregory, Flip Wilson, Pigmeat Markham, Pryor, and Murphy, but also Steve Martin and Woody Allen. It’s this refusal to limit himself as a strictly “Black” comic that made Rock’s perspective so challenging and palatable to a diverse mainstream audience. Rock steps into a yawning chasm between black America and White America as an objective arbiter, willing to call bullshit on both sides at a time when those lines were heavily drawn and lined with barbed wire.

Chris Rock brought an incisive hell fire brand of “cut the shit” logic to the war on drugs, religious dietary restrictions, the prison industrial complex, and the impossibility of platonic friendships, but it’s when the conversation centered around race that brought out the best in this hour. (The hypocrisy of “enlightened” white liberalism and his screed on “articulate” as damnation by faint praise in relation to Colin Powell is particularly affecting).

Rock’s depiction of OJ’s motive isn’t quite as iconic as the titular joke for this piece but it might be funnier and smarter. If Marcia Clark had tagged in Rock for closing statements, perhaps the verdict would’ve come out differently. The bit also displays his mastery of rhythm and hooks, with jokes operating like music and riffs like verses revolving around a devastating recurring punchline (I’m not saying he should’ve killed her (beat), but I understand.”). His center aisle approach to race is epitomized by his riff on OJ, laughing at how overly invested both white and black people were for their “side” and observing that the OJ trial was in fact an issue of celebrity. (“If OJ drove a bus he wouldn’t even be OJ, he’d be Orenthal the bus driving murderer”.)

But it’s the titular bit, airing the dirty laundry and letting the world in on a conversation that was being held in hushed tones behind closed doors that proved a career changer for Rock and a game changer for how we discuss race. What Rock brought to race comedy at the time was nuance. The humor had been dominated by the sort of broad “White people be like/Black people be like” generalizations that dominated the Def Comedy Jam circuit clubs for decades.

The critique itself is problematic, steeped in conservative bootstrap self accountability rhetoric. There’s no acknowledgement of the systemic ills that potentially created the behavior of both black and white poor people acting in ways society and Rock deem improper. But to simply stand up and express the frustration of a black person with people of his own color was both revolutionary, and crucially, obvious. The bit became infamous. Rock retired it immediately after the special because he felt white people believed it gave them license to use the n word, Barack Obama quoted it once on the campaign trail in 2008, and Rock became the biggest comedian in the world. It led to a groundbreaking show on HBO and a career in film that probably should’ve been better than it was. But Rock expanded and complicated the way we think and discuss race in America forever, and for the better.

Dave Chappelle has aged into a cigarette smoking, riffy truth teller, his bits loaded with historical anecdote and surreal confessional windows into his personal life in the mode of his heroes, like Pryor and of course, Rock. But the best of Chappelle stand up came earlier. His greatest early bits are prolonged, fantastic fictional tales with a novelistic eye for characterization and detail. They are larded with observation that makes the beyond belief stories feel real and resonant. There are messages about race, poverty, and romantic relationships that hit as hard as any heartfelt Maron testimonial, they just happen to be occurring in Dave’s imagination and have the general tone of a Looney Tunes short. His delivery is all rubber kneed flailing and an array of hilarious voices. In other words, it’s vintage Cosby.

From the beginning, the comedy of Dave Chappelle was oriented around the absurd hierarchy of privilege. Places where issues concerning race rub up against gender or sexuality or religion. The idea that some pain is more valid or important than others and the implicit hypocrisy in that measurement has fascinated him since his inception as a comic and there are dozens of jokes illustrating this from his seminal show or his standup.

It’s his penchant for the fantastic, his love of character, and the surreal that made the sketch show his ideal medium. Chappelle could present his heightened scenarios and insane characters five minutes at a time, bookended by some observational humor and a De La Soul performance. It took the format of SNL, In Living Color and other sketch shows and blew them out. An episode could have a single theme it was pursuing, or built around a drawn out 20 minute sketch with commercial breaks, or it could be a series of chaotic, scattershot sketches. This willingness to follow a joke wherever it may go, length of time or pacing be damned, changed the sketch show and set a new precedent for comedians like Carlos Mencia, Amy Schumer or Keegan Michael Key and Jordan Peele.

Chappelle didn’t just hit on a new format for half hour television, he also made one of the most consistently funny, intelligent and relevant comedy shows of all time. It was alternately stupid, satirical, horny, heartbreaking, incisive, inventive and insane but always hilarious. Somehow, even with that towering resume, its best, most important bit, the nine minutes you should watch if you want to understand why The Chappelle Show mattered, closed out the first episode of the show.

I grew up in a small town in Upstate New York. It was a diverse place. There were many people of color, a lot of rednecks, but almost no Jews. As a result, we were easy marks for the rednecks scared to use to the n word. From a pretty early age, a defense mechanism I developed whenever Jew-bashing started at the cafeteria or in the locker room was dropping into a growly redneck patois, something along the lines of a Larry the Cable Guy type of schtick coming up with colorful, detailed, dark, and descriptive anti semitic humor that would regularly outpace and dismantle would be tormentors. It took me years to figure out why this bit was so effective, but eventually I got it. Racism isn’t funny, but racists are. By laying bare the stupidity of people who believe in lazy generalizations about groups of people, you’re not laughing at the stereotypes, but the people dumb enough to buy into the nose shape of all Jews or in Clayton Bigsby’s case, the scent of black people.

“Clayton Bigsby” is presented as a 60 Minutes style profile, a device The Chappelle Show would revisit often. It’s crazy and absurd, but the story of Bigsby could also be viewed as a tragedy. It’s a story about learned hatred, a little black blind boy no one ever had the heart to tell the truth. He takes his learned hatred and ironically becomes an effective cult peddler of that hate as the author of the books Dump Truck, N***** Stain, I Smell N******, and “N***** Book.

I had forgotten those titles and just re-hearing that joke as I watched the segment to prep for this I burst out laughing. As Chappelle has said, it’s a complicated laugh. A gut punch he gets by putting vile hate speech in the mouth of a monotone Mike Wallace like reporter. But I believe it’s rooted in a mockery of Clayton, who is racist in the laziest and most boring way imaginable. He would be a contemptible character if it was even remotely possible to take him seriously, but Chappelle plays him like a Southern fried moron, taking a cheap shot with the blind angle and playing it for laughs but everything from his accent, to his dress, to his articulation of his hatred (“They Stink!”) is meant to display how stupid he and his belief system is.

The sketch goes on to set up several hypothetical situations for Bigsby to react to. Cornered by racists looking for an easy target, they’re shocked when he responds to their taunts with his own full throated hatred for an imagined black target he believes they’re ganging up on. In traffic, he accosts a group of white kids blaring rap music he confuses as black who promptly celebrate being called the n word. Like the show itself, the skit is a problematic joke particle collider showing all the strange and blurry lines where race, expectations, cultural cache, and systemic oppression smash into each other. All Dave and his dark, vivid imagination could do is laugh at the irony and hypocrisy, until one day he couldn’t laugh anymore.

Chappelle made race based ignorance the butt of most of his jokes. Like Rock, that could extend to black people, but once again there was a surreal, heightened quality to his absurd scenarios. One of his best bits imagines a Real World in which a white person, Chad, lives in a house with black stereotypes. Chad ends up losing his girlfriend as two of the housemates run a train on her, he’s knocked out, robbed and raped, his Dad gets shanked, and he’s voted out of the house.

There is a danger to laughing at the stereotype, the type of behavior Chris Rock made his bones calling out, but what we should be laughing at is the absurdity and stupidity of the stereotypes, the lack of humanity it would take to shank Chad’s father for no reason, the white nightmare of blackness animated and played up for all its absurdity. It’s a normalizing of a conversation about race no one was willing to have for far too long, and in their high toned mockery, Chappelle and Rock humanized the conversation, made it okay to say this is frustrating, and sad, and stupid, and funny for all of us.

2. The Simpsons (1995) – “And Maggie Makes Three, ‘Do It For Her'”

“Why aren’t there any pictures of Maggie?” A simple enough question as the Simpsons sit around a photo album on the couch during mandated family time with no TV. The answer gives us a comprehensive history of television’s most important family and for me, the greatest episode of television ever made.

Picking a favorite episode of The Simpsons is like choosing a favorite child, which is ironic because that is the very taboo subject of my favorite episode. Maggie was an unplanned and unwanted pregnancy, and the episode doesn’t look away from the dark side of how having a child can be a frightening and life altering occurrence.

The Simpsons had used the flashback to great effect before. The device is one of the many benefits of animation the show would utilize. It had become something of an annual tradition. We’d already seen the origin of Homer and Marge’s relationship in Season 2, Marge and Homer’s engagement in season 3, Lisa’s first word in Season 4, and randomly, Homer’s stint in a barbershop quartet in season 5. But it’s in season 6, arguably the show’s best season, smack in the middle of its prime, clicking on all cylinders, that we got its best flashback, with the family’s mute infant as its unexpected subject.

As far as the straight humor goes, And Maggie Makes Three isn’t just very funny but also great at playing with our expectations as well as the parameters of its animated medium. The prolonged joke in the middle of the episode’s second act, where Patty and Selma conspire to ruin Marge’s attempt to break news of the pregnancy to Homer gently by telling Springfield’s two biggest gossips (at opposite ends of the phone book), followed by Homer’s impossible density as he goes around town unable to comprehend his impending fatherhood is a masterpiece. As are the many jokes throughout the episode as Homer plays the unreliable narrator in his flashbacks.

We get a mock Die Hard opening, Bart intervening to make Homer’s head explode like a balloon, and a great set piece in which after much research Homer tries to drum up business at the bowling alley by firing a shotgun in front of the place, screaming at foot traffic. Lisa implores her father to tell the story as it really happened, only to discover that was what really happened. These are things that would be impossibly complicated and expensive to convey in live action. The Simpsons used animation to make incredibly complicated jokes shorthand. Watching early episodes like this is watching The Simpsons writer’s room understanding the freedom that comes with animation and exploring it for the first time.

But what makes this episode and The Simpsons truly unique is the gigantic pulsating heart at its core. Norman Lear is the clear antecedent for The Simpsons in his telling stories about humble blue collar families maintaining their dignity and love for each other in the face of imperfect circumstance. The Simpsons simply perfected the model. The show is groundbreaking in its willingness to look at the darkness in its titular family’s dysfunction without flinching.

This particular episode follows Homer as he finally crawls out of debt to live out his dream working in a bowling alley, only to have that dream robbed by life and chance. His reaction to “another mouth to feed” is selfish, brutal, and above all else, real. The episode explores fatherhood, the financial strain and anxiety that comes with an unexpected pregnancy, the fear of unwanted responsibility you may or may not be ready for. That this was all achieved by yellow four fingered cartoons is something we take for granted now but 20 years ago was revolutionary.

The final three minutes of the episode are perfect. “And Maggie Makes Three” spends most of its runtime subverting our expectations of what it means for a television family to get pregnant. But all it takes is a first look into his newborn daughter’s eyes for that selfishness and cynicism to melt away. We laugh at Homer and the almost depressing dream he’s achieved, we laugh at his stupidity, but by the end we see his good natured decency and the show delivers the uplifting, satisfying chocolate center television and narrative structure demands. It turns out there are many pictures of Maggie; Homer has covered the walls of his office with them as a daily reminder to himself and us, of the sacrifices we make for our children.

1. The Larry Sanders Show (1992-1998)

Every other entry on this list is a specific joke or device or idea. For Garry Shandling’s groundbreaking show I tried to isolate a single gag, or character flourish or moment to focus on, and then I gave up.

It’s the very idea that you can make a show about making a show with celebrities playing themselves that was so important. Shandling was at one time in the running for Johnny Carson’s position and he brought his experience to creating the show, often tightroping events that occurred in the midst of the late night shuffle and giving us a look inside the halls of the studios where these shows are produced.

It’s Hank warming up the crowd that many episodes fade in with, the awkward pauses during commercial breaks where the forced amiability we see on camera goes away, writers wringing their hands as Larry butchers a joke because his timing is off on a given night, the detail and care that went into showing process was unprecedented. The show jumped on the idea of simulated reality at the very moment reality was taking its place as a primary form of entertainment. Found footage, the mockumentary, this stuff was floating in the ether but The Larry Sanders Show tied it all together.

The thrust of this list, the idea every joke is getting to in one form or another is the concept of truth in art. How the art we consume is made, discussing its very construction, cutting through the artifice and bullshit, and showing us how a well imagined premise executed with full commitment is more entertaining than familiar, pleasant construction. No show was messier, uglier, funnier, and most importantly, more committed to honesty than The Larry Sanders Show. It was a six season exploration of the minds and egos of the people who make the art we love. It was brutal in its interrogation, fearless in the depths it was willing to plumb, and constantly revolutionary in its inventiveness.

If I had to isolate a single joke from the series to highlight, it would’ve been David Duchovny’s recurring role playing himself. Before The Larry Sanders Show celebrities playing themselves were rare enough, I can’t think of any such meta flourishes but I’m sure they exist. But Duchovny isn’t only playing himself, as so many did on LS, he’s playing a version of himself with a drawn out gag that has him crushing awkwardly on Larry. The show and its guests grant us a look onto the floor in the sausage factory that is at once incredibly revealing but at the same time its own sort of artifice. Brett Favre’s cameo in There’s Something About Mary narrowly missed this list largely because it never could’ve happened without Larry Sanders, same for Neil Patrick Harris’ career resurgence with Harold and Kumar Go To White Castle, Wayne Brady on The Chappelle Show, and what is by now hundreds of meta characters playing themselves and leaning into or away from our expectations. It’s now a given that celebrity and pop culture can interact in a meaningful way in our fictional worlds but it wasn’t always so.

As a comedian, Gary Shandling loved to push boundaries and comfort zones. The recently released HBO documentary about him made by his protege Judd Apatow lovingly details his relentless pursuit of honesty and clarity. In his show about a show, with a show within a show, with its myriad of insecure, agenda-riddled desperate people Shandling exposed his own demons, those of his artist peers and many of our own.

Sanders is a dark, cold, closed off show. The people who make it aren’t likable, warm, or friendly, there is little to no growth or development of the static, shallow characters, it isn’t clear any of them really like each other—they certainly don’t like themselves. They cycle through side gigs, lost ambitions and dreams, marriages and friendships. They gossip and back-bite, root against each others success, social climb and more often fall on their faces. And yet they’re a dysfunctional family, a group of seasoned professionals working in service of a purpose, which happens to be a deeply mediocre late night television show but that’s besides the point.

Even though it closed the first season, the first episode the show ever shot was called “The Hey Now Episode”. In it, Sanders asks a question the show would circle constantly: “What is Hank Kingsley’s purpose?” A bumbling ego-maniac, Tambor’s sidekick Hank Kingsley is the show’s id. The most craven and grotesque avatar of the desperation at the center of show business. Larry and Hank spend the episode squaring off over Hank’s dedication to the show and his contribution. At the conclusion, Larry realizes the show relies on their dynamic and he apologizes. “I just can’t help it, I’ve turned into an asshole the last couple of years.” Hank responds, “That’s okay. I’ve turned into a moron. I mean, let’s have a good time with it.” I couldn’t think of a better mission statement for the show.

In reviewing this list, what I think I can draw from it is that it isn’t so much the content that matters the most in importance and impact on sense of humor, but form. People are still people and jokes are still jokes, the modernization of the delivery system is what makes humor so different than it was 30 years ago. The entire concept of meta, the breaking of the fourth wall, our heightened awareness of the process of humor and entertainment is what’s changed. Simply put, there’s no mind, no sensibility, no movie or television show episode or stand-up bit that did more to affect the way we tell jokes and process humor than Gary Shandling and The Larry Sanders Show.