A Wanderer’s Guide to Chester Watson

A Chester Watson beat is the musical equivalent of leaping through a zero-gravity vacuum. Yousef Srour breaks down his ten essentials songs.
By    March 30, 2022

Photo via Chester Watson/Instagram

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Yousef Srour keeps taking breaks from finishing ‘Dilla Time’ because he keeps looking up used MPCs on eBay.

Chester Watson is a mastermind with his pen. Woozy and always with some distance, he raps with ease – the self-proclaimed, monotone samurai. It’s music to microdose to. Chester gazes into his sword and he sees a bitter reflection, an image doused with the scripture of past, present, and future. On his latest album, 2020’s A Japanese Horror Film, he portrays a solemn wanderer, a man scrolling past the depths of the inner-realm, a land ridden with ancient temples and yokai. He pulls you in just close enough to hear whispers that sound like the faint crackle of a spliff inhale.

It’s a rap Auguste Rodin sculpting a post-modern version of The Thinker. Kneeling over, elbows on his thigh, Chester ponders the existential. What is existence when you’re a self-proclaimed god? It’s the pose of an award-winning producer, hunched over his mixing board, working with an array of drum machines to make a lo-fi beat that sounds like a long-lost memory. Chester is methodical; his effort is made clear with every line. His rhymes are pragmatic. Chester’s a young MF DOOM with a cloud mask, lacing poetry with weed smoke. A skater at heart, his music matches the momentum of his left foot grazing the cement, propelling his board forward into the unknown.

The more I skate, the more I understand Chester’s philosophy. It’s the exhibitionism that comes with cars swerving around you because the sidewalk is too populated; it’s the inadvertent attention that comes with wearing streetwear and independent clothing brands like Chester’s signature “I Love Ugly;” it’s the unhurried stroll of living on your own time. As I practiced tricks at my local skatepark, I sat with his lyrics. While I kept myself busy with ollies and kickflips, I tried to memorize every word of “Trident” and “Phantom.” The beats continued to loop, and at my most desolate, the flatness in his voice was all I could bear to hear.

A Chester Watson beat is the musical equivalent of leaping through a zero-gravity vacuum. “Time Moves Slower Here” in the realm of our antihero – whether that be due to the detachment of time borne from a tab of acid or due to the THC attaching to cannabinoid receptors in the brain. Chester Watson lives in another plane of existence. These ten songs are a glimpse into his celestial form.

“Time Moves Slower Here”

Like a pebble skipping on still water, the beat ripples in your earphones. Chester Watson sounds like he’s studied everything from clocks to quantum physics; on “Deep Sea Tundras” he notes, “Time isn’t a vector, no/Time isn’t a scalar, no/Time is just perspective.”

Chester is patiently waiting for the acid to kick in – it’s an introduction to his form of neo-psychedelia. His world is slowly morphing into Salvador Dalí’s The Persistence of Memory. Everything melts around him. The clocks droop down to the floor; they’re all ticking at different speeds, some clocks even programmed to different times. The bass drum kicks emulate the slow ticks of a grandfather clock. The synthesizers cascade. They swish back and forth to match Chester’s every word, giving himself free rein over the self-produced track.

Chester is a disciple of darkness; the witch doctor’s protege that lurks in the night, snatching Supreme trucks and daffodils as if he’s waiting to be caught. He’s unfazed. He enjoys the tranquility; his voice doesn’t waver and the beat guides his intonation. He holds his breath as the “warped record” changes pitch ever so slightly, and he continues without skipping a beat when the needle comes back down to its rightful place on the disc.


I found Chester Watson through Spotify Radio after listening to JPEGMAFIA’s “Rainbow Six.” I was seeking an “experimental” sound, but what I found instead was a teenage outsider. My first impression of him was drenched in the buzz of the low-frequency wobble, as though I was seeing a reflection of myself in a house party’s bathroom mirror while muffled subwoofers bleed into the acoustic space. Chester’s voice comes off as crisp and articulate. The minimalist beat quivers underneath him. Bass drum hits bellow, hi-hats flutter, and the podgy bassline traces him as an antihero. He’s immoral and his tone is standoffish. He doesn’t want to talk to anyone, hence the low-register grumbles.

There’s an unspoken loneliness in Summer Mirage that doesn’t appear in the rest of Chester Watson’s music. He borders on the braggadocious, but it comes across as a dissociated stranger reveling in his own accomplishments for the first time. Chester is cryptic, speaking in obscure references from his personal life. The sentiment is clear; he doesn’t want you to know more than you need to. Chester’s a closed book, locked away “at home making mad beats.”

“Museums” is the perfect gateway to Chester Watson because it’s a deductive approach to his psyche. Without “Museums” there’s no understanding of who Chester is when he’s alone. It’s the prologue to his withdrawn, enigmatic persona. He seems blasé to any lifestyle that isn’t centered around synthesizers and MPCs. He’s abrasive; his use of “c*nt” is jarring and as he “scrapes resin from a bong,” he seems like the last person you’d want to surround yourself with. Still, he’s much more complex than a couple of grimy bars.

“Soundless / Daydream”

On “Soundless/ Daydream,” the beat crackles with the surface noise of a dusty record being played at one of the countless cafes on Rue Montorgueil. Chester’s voice is groggy, he’s hungover with the sniffles, smoking to ironically bring himself back to earth.

I picture the song being recorded in an empty, sublet apartment. Huge windows let in the flood of light from the break of dawn, an inflatable mattress fills up the living room’s empty space. It’s bare bones, and as producer Ol’ Burger Beats continues to set the ambience, Chester’s memories from the previous night make their way into his still-inebriated consciousness.

Nonlinear but still oddly specific, the song recounts a story of Chester in his most intoxicated state. The keys play like the backdrop of a late-night jazz club (not too far from Chester’s drunken alley). The harp nestles itself in-between the piano chords to give the song its dream-like quality. Chester winces through the tale while maneuvering between memories and reality. Ever so often, there’s a baby-like cry in the background of the instrumental. Maybe it adds to the nostalgic quality of the music, or perhaps Chester heard the song as he trudged through dark, dimly-lit boulevards and the sound has become inescapable.

Traversing through Europe in his late-teens, Chester acts the part. The monotony in his tone is comforting because he doesn’t sound proud of what he’s done. He half-heartedly remembers, “I think I puked on my Huaraches” and “I can tell that this girl didn’t want to sit next to me/On the train I smelled like alcohol and sex/Weed and ecstacy.” Chester’s brutally honest with himself. That’s his appeal. He refuses to paint himself as some sort of exuberant, happy-go-lucky auteur. He wants you to see him in the same way that he perceives himself: a specter. A suicidal insomniac fueled by sake and blunt wraps.

“Cool Hand”

“Cool Hand” follows Chester’s past life in the Spaghetti-Western era. L’Orange recreates the frontier of the Wild Wild West for Chester and Jeremiah Jae, preluding two cowboys’ shootout. L’Orange samples Elmore Jackson’s 1962, obscure blues classic, “Anna Lee” to construct a wooden saloon, complete with dust and tumbleweeds outside its storefront.

Chester’s a method actor. He pours “the Jack in the chalice” and prepares for duel. But just like the rest of Chester Watson’s discography, the persona comes effortlessly; to him, it’s just a quick improvisation. The dispassionate flow suits him – a grimacing gunslinger with scuffed, leather-padded boots. He doesn’t say much, but his presence immediately requires your attention.

“Change perspectives” and Chester swiftly becomes a modern-day vigilante. Rooted in the mentality of the Panthers, still infuriated by the KKK, he time travels and finds himself rapping as a freedom-fighting renegade. The juxtaposition here broadens the schema of Chester’s self-perception. He’s an old soul, and perhaps in one of his past lives he would venture endless lands on horseback, but it’s always been the same fight. Whether it’s a spirit quest on ayahuasca or “smoking Purple Haze on the way to the spaceship,” Chester’s experiences remain boundless.


As a skater, there’s a moment of weightlessness as both your feet are perpendicular to the direction you’re headed. You feel free as you slightly nudge your weight from side-to-side, flowing back-and-forth like a kindergartner trying to draw a straight line. “Trident” brings out that same feeling. The bass drum kicks skip, patiently waiting for Chester to catch his breath amidst the light boom-bap.

A young Q-Tip at heart, Chester experiments with different frequencies, with the beat looping a delicate soundscape that sounds like the inside of a wind tunnel. Think “Waves” by Joey Bada$$ but even more laidback. He wonders if his girl’s “booty dynamic’s confusing physicists” and the environmental impact of his smoking habits. You have time on your hands when you skate; free time to unpack the metaphysical.

Perhaps that’s why “Trident” doesn’t have a hook. Thoughts are rarely linear. They’re prone to being tangential. Life is aimless, so Chester advises to “enjoy each other’s company.” His philosophy isn’t complicated. Chester’s mature for his age. Equal parts starving artist and Buddhist monk, his skateboard allows him to drift into a clear space. Breathe in, let out your worries, and skate on.


I once listened to “Phantom” twenty times, if not more, in one day. It’s addictive. By the end of the 2:15 minute runtime, your brain will crave the simple yet hypnotic whirly piano. I like to think that Chester Watson brings with him the revival of A Tribe Called Quest, toying with a four-bar phrase that brings back the imagery of the lanterns that illuminate Luigi’s Mansion.

The magic of “Phantom” comes from Chester’s articulation. As listeners, we’re used to hearing a despondent alchemist carefully plotting his every step. When listening to “Phantom,” however, Chester’s whimsical. He wants you to know that he’s not some Kanye who’s making “five beats a day for three summers.” When he released this song in 2013, he was working all day, his homie was “slinging trees,” and they were eating greasy, 2-piece meals together from KFC. He’s 15 years-old and as he puts it, “They hella mad ‘cause I’m handsome.” He’s young and carefree, suave, and just itching for someone to call him out on his bullshit.

The music video is compilation-esque where he mainly raps motionless, head-on to the camera, splicing together mafia and action sequences from classic films. It’s surprising because the song is a single verse. It’s Chester strutting down the sidewalk, moving with swagger, skateboard at his side. It’s a showcase of technical excellence. Using onomatopoeia to describe the “ratta-tatta” shooting from his tool and the “click-clack” of tires, Chester casually coasts through the track as if it was a freestyle.

It would be no surprise if a sizable portion of his 10,000 hours spent mastering the craft were solely dedicated to memorizing Madvillainy front-to-back. “Phantom” has no hook because it’s his introduction – a short-lived soliloquy about the DIY lifestyle of the breaking Nü-Age talent.


“Fog” is one of the few songs in Chester Watson’s discography that showcases the turmoil in his life. Cognitive dissonance seeps into his every action. The first lines are vulnerable – “My girl told me that I smoke more than I eat/Need to defog/ I had to agree… I agree, I agree..” His voice trembles and he sighs in acceptance. Everything around Chester is bleak and murky. He moves reluctantly, disconnected from everyone.

The instrumental hobbles alongside Chester. He’s groggy and mentally drained from astral projection. He can barely cope, adapting to the pitfalls of fame and his reclusive life as an independent artist. Life is dreary; the instrumental hints at the journey home. Yokai murmur in the forest, surrounded by sound bowls and the plucks of a Japanese koto. The beat holds its breath as it waits to see Chester’s fate. A forewarning choir chants the same five notes over and over again, but it feels hollow. Chester’s mind is fading; was his quest as a samurai even real, or just another overbearing high?

Instead of answering the question, he relapses into his old ways and restocks his weed supply. He ponders the existential because reality seems to be too fleeting for him. Chester shares that “Kent said ‘I think we need to cop more trees’/ I looked at the weed, and I had to agree… I agree, I agree.” This blatant paradox highlights the emptiness that lives inside of Chester. At the whim of the people around him, he has trouble moderating himself. He wants to be two different people at the same time and is disappointed in himself for repeatedly falling short.

Chester becomes a version of himself that’s been jaded with overwhelming anxiety. He seeks solace but hasn’t the slightest clue where to find it. As he grimly puts it, “Man, I miss the days when my thoughts were so simple.” Chester just wants to rhyme and make beats. He’s endured enough pressure and coy games.

“Cloud Mask”

As a kid, I remember playing with incense smoke, lighting a flashlight in a dark room and twirling my fingers to change its movement. The clouds hold within them an undisclosed wisdom, insight into an immaterial world.

The instrumental is eerie – it brings you to an empty terrace in the city. The reverb works to blur the sound, whirring as if cars and life are quickly passing by.

Chester Watson modestly relays that, “I’m just a wanderer roaming the stars.” The song gives purpose to Chester’s colorless flow. The music is dazed, teetering on the brink of devastation as one does in the eye of the storm. His smoke break is an act of self-medication. An introspection into every part of his being, he questions the literal and metaphorical chains that weigh him down, and he reminisces about the artists that molded him into who he is at heart – Portishead, Yasiin Bey, Nujabes and DOOM.

It’s difficult to appreciate the present moment when miscellaneous qualms constantly infiltrate his mind. It’s hard to even sleep. The song was made for the night. Although the cloud mask barely covers his face, it lets Chester breathe in the stardust, steering him towards a path of self-actualization.

“Camels and Cranes”

“Camels and Cranes” is Chester’s own iteration of “Electric Relaxation,” as he conducts an expedition into space. Everclear when he says, “We still bumping Midnight Marauders,” this is one of the earliest exhibitions of Chester’s languid presence. He rhymes in the abstract. He tells stories of the “magical spliff” and how the clique he surrounds himself with “is filled with many villains.” But alongside his stories is a rebirth of wordplay and the unknotting of tangled words that smoothly pass into each other like lockets on a chain. First and foremost, Chester Watson is a poet. The chorus is riddled with consonance, depicting “fish bobs” and “lobs of snot.” The enunciation of his lyrics set him apart from any rapper in the modern art scene because of the weight he places on the sound of words. Just like his use of onomatopoeia, Chester recognizes the importance of sounds in rhyme schemes, and instead of defining his music with earworms, he reaches for flexibility in his tongue, conjuring up lyrics that are entertaining to both listen to and to vocalize on your own.

Art Vandelay produces the track, panning synthesizers from ear-to-ear, with crackles of surface noise outlining Chester’s tribute to vinyl-cut, ‘90s jazz-rap. There’s a bit of boom-bap, but ultimately, the song is a futuristic shadow boxing match. Chester tries to constantly go bar-for-bar himself, channeling his inner-DOOM. Tin Wooki even features a song produced by Madlib, so it makes sense that Chester laces up his Grim Reaper low-tops to be considered a competitor amongst the elite.

“Drive By Earth Music”

This song could be the last thing I ever hear, and I would be perfectly fine with that. It belongs in the same family as “Suicidal Thoughts” by Biggie and “Solace” by Earl Sweatshirt. It’s the final track on Chester’s 1997 EP, titled after his birth year. A tape deck ambiently loads up and the same downtempo electones from Shigeo Sekito’s Special Sound Series begin to fill the room.

The beat floats like Chester does on the cover, bubbling atop gusts of wind to capture the elusiveness of death and purgatory. With Chester nonchalantly dissecting his life into moments and “sometimes,” the song feels like a cryptic nod to the Grim Reaper. He faces death, but barely acknowledges its presence. The track is draped with reminders of demons and the shadow of the recently-deceased LA-legend, Nipsey Hussle. Tragedy looms, but Chester refuses to spiral. “Drive By Earth Music” reminds me of mindfulness meditation, where your mind stays centered as thoughts are allowed to roam freely with no engagement. He reaches a transcendental space, guided by the advice of his mother and the lessons he’s learned from ballet and his performances in Europe.

“Drive By Earth Music” is the song that plays as you sit on your rooftop and take in the awe-inspiring landscape, whether that be open plains or the electric circuitry that becomes Miami after dark. Chester has moved past material possessions. He wants to “grow and improve” as a person, as well as in his craft. Trapped in his early-20s, he feels subdued by a world that can feel passionless. “Sometimes I want to die/Sometimes I just need time and space.” The lyrics are foreboding, but in being so, they feel more personal than Chester has ever been. There’s no persona; there’s no character here but himself. He mutters again, “Sometimes I just need time and space.” The song is nothing more than therapy for Chester. He repeats the same phrase over and over to himself like a mantra. The words of a young man who is fearful of the world to come. The words of a young man who is worried that, for once in his life, time will keep moving forward.

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