The Weirdest Rap Collaborations Of All-Time

Joel Biswas swims through the abyss of '90s/early 2000s rap-rock to track down the best (and worst) of the genre.
By    January 16, 2018

Joel Biswas is not here for the Britney Spears revival.

It’s surreal to think that rap is old enough to be historical, let alone kitsch, but nostalgia devours all—including the definitive cultural flowering of my youth. Beyond the despair of this realization lies the pixelated YouTube wormhole of rap’s thinnest ideas and most forgettable moments—an invitation to pan for fool’s gold in the gravel pit of defunct pop culture.

When it comes to kitsch, rap’s relentless desire to get money across coasts, regions, labels, and aesthetics makes for rich pickings, but the true fetishist’s delights are to be found when rap and pop started fucking with each other in earnest. The major label approach of pairing pop and rap acts with all the restraint of a Summer Jam after party combined with rap’s tendency towards hubris was a perfect recipe for stillborn pop trash. Thus, ODB and Mariah had lovable Beauty and the Beast , chemistry but the Yin Yang Twins and Britney was the aural equivalent of an Eyes Wide Shut orgy. “Walk this Way” blew open the doors of rock-rap fusion but one listen to P Diddy’s “Kashmir” is a more powerful call to self-harm than playing a Judas Priest record backwards in a Midwestern teenager’s pot-scented bedroom circa 1982.

In another era, wading through this vast sea of cultural detritus would be as daunting and self-defeating as cataloguing Jamaican dub plates. Today you can just drop in to a YouTube playlist and let this tragicomic taxonomy of shit wash over you. Glaring artistic failures. Crass commercial gambits. Shameless entrepreneurialism between rap cliques with irreconcilable stylistic differences. Derivative production that spans the range of ’90s and early ’00 clichés. M.O.P. demonstrating that they can and will get it blacked out over anything. And occasionally, startling moments when rappers manage to transcend the sonic car crash that surrounds them.

Looking back, it’s not hard to see why this music never mattered in the first place. Now that nothing matters, the temptation to deaden higher brain function by trawling the dim recesses of the internet in search of the exact moment we killed God is imperative. For those with time to waste, I offer critical re-appraisal of ten prime offenders below.


Crazy Town“B-Boy 2000 (Feat. KRS-One)”


For a genre that shamelessly borrowed from rap only to do so little with it, it’s a reliably cheap thrill a when a real rapper shows in the creatively barren hinterland of rap metal. Admit it now – whether it’s vintage-era Premier and Mef in a cypher with Fred Durst or Jay Z conquering the suburbs with Linkin Park, resistance is futile. But just when you’re about retrieve the two-foot glass bong from the attic, pull the curtains and take it back to ‘98, enter the rap–skate-metal juggalos Crazy Town and Bronx rap luminary KRS One to remind us that some things cannot ever be taken back.

Listening to this song made me sad and angry on a second-by-second basis. This isn’t even the worst of Kris’ crossover dalliances – previous efforts include bringing rap justice to Prince Be of PM Dawn and getting a platinum plaque for hype-man work on REM’s “Out of Time”. Nevertheless, his phoned-in toasting and old schoolisms are just enough to momentarily anchor the listener in a sea of torrential suckery and prompt a flicker of nostalgia.

Score: 6/10


Nelly“Over and Over (Feat. Tim McGraw)”


Not content to have already given us one of the most annoying collaborations of all time two years earlier with Kelly Knowles and “Dilemma,” Nelly again made moves like Hammer to team up the only artist who could deliver him the lucrative flyover demographic—AOR country stalwart Tim McGraw.

The accompanying video appears to be a high gloss ‘making of’ in which our two protagonists joined only by a split-screen, wake up and go about their typical day making power moves, each eventually retiring to a private jet as the track fades out. These two are clearly simpatico, and even if we don’t ever see them hang, the proof is in the undeniable chemistry on display in this, the most cynical country hip hop stadium banger since Coolio brought back Kenny Rogers.

Score: 6/10


Q-Tip“End of Time (Feat. Korn)”


The standard narrative is that the shelving of Kamaal the Abstract was a travesty of narrow-minded record label politics denying Tip’s brave steps to expand his sonic palette post-Tribe. I’m now convinced that it was justifiable punishment meted out by L.A. Reid for the appearance of this song “Amplified.”

Things start off okay with a doomy rock-infused bounce featuring guitar fuzz that’s kind of interesting until it becomes a camp Korn song about dystopia with vocals that sound like they were laid down with a dictaphone. I feel personally affronted as I reflect on the fact that Tip actually featured them on his album when in a parallel universe he could have been rapping with Phife or recording more jazz fusion. YouTube has helpfully added Korn featuring Xzibit to the ‘Up Next’ column, but I’m going to see if we have any Cocodamol instead.

Score: 5/10


Chris Cornell“Part Of Me (Feat. Timbaland)”


This would have been more fun to listen to and write about before Chris Cornell died. As it stands, the commercial calculation driving this pairing is so glaring that “Part of Me (Feat. Timbaland) could have been the product of a focus group exercise. But then again, by 2009 Timbaland was deep into his imperial phase of rock so rudderless in general that capitalizing on Chris Cornell’s smoldering pop good looks for a dance floor smash might have been a smart play. You know what’s even smarter? Throw in a rejected Bacardi ad concept for the video so Cristobal slay with the Boricuas. You can almost see the fingerprints from some coke-addled A&R all over this. Cornell looks deeply lost throughout the video. He did have the dreamiest eyes.

Score: 3/10


Britney Spears“Boom Boom (Feat. Ying Yang Twins)”


Britney might be the light relief I need right now while the painkillers kick in. I’m instantly hooked by an expensive sounding beat that has me checking for a Timbaland credit. Britney is cooing about how hot, alluring, and available she is while Ying Yang are getting things expectedly crunk but seem overawed by Britney’s bad bitch aura. It’s all a bit “Black Snake Moan” meets a mid-2000s frat party at college in Central Florida. The stink of this isn’t going to come off with a shower.

Score: 6/10


Brad Paisley“Accidental Racist (Feat. LL Cool J)”


Brad Paisley and LL team up to heal America’s racial wounds through the medium of rap-country cornpone. It sounds like an overlong Christian ballad that explains the origins of America’s troubled Southern racial history instead of Deuteronomy. It would be wrong to trivialize such a weighty matter with a conventional pop verse-chorus structure but the below lyrics do get repeated in a chorus-like manner.

‘Cause I’m a white man livin’ in the southland
Just like you I’m more than what you see
I’m proud of where I’m from but not everything we’ve done
And it ain’t like you and me can re-write history
Our generation didn’t start this nation
And we’re still paying for the mistakes
That a bunch of folks made long before we came
And caught between southern pride and southern blame

Rather incredibly, it’s even worse set to music. LL tries to liven things up with absurdist interjections and generally fails. (“RIP Robert E. Lee but I’ve gotta thank Abraham Lincoln for freeing me, know what I mean?”). The song is as slow and stultifying as minority voter registration protocols in Alabama and an abject failure as both art and pedantry. I’m going to pause for a bong hit.

Score: -3/10


Insane Clown Posse“Insane Killers (Feat. Vanilla Ice and La the Darkman)”


The highest aspiration for this music would be that it could be a soundtrack for the planning of a high school massacre. In reality, it’s a better backdrop for solvent abuse.

Score: 0/10


Gucci Mane“Poltergeist (Feat. Talib Kweli)”


Against all odds, this is actually excellent. Talib sounds invigorated over trap beats and strangely becomes the first rapper to ever rap in double-time on any of Gucci Mane’s 12,374 tracks. Remember when Jay rapped about how he could be “lyrically Talib Kweli?” Fifteen years later, Talib channels Jay instead and nails it and gets noticed. In fact, backpack stalwarts didn’t take kindly to his foray towards the Dark Side—hence the knowing title of his latest album, Prisoner of Conscience—at least according the comments on YouTube. Wherever you stand on this controversy, the winner is shameless, opportunistic cross-regional crew love for some quick ducats.

Score: 7/10


Victorian Beckham“The Dude (Feat. Ol’ Dirty Bastard)”


Some things can only be experienced. I’ll let this gem from Victoria Beckham’s legendary lost solo album speak for itself, except to say that:

a) I hope ODB did this for drug money.
b) It’s worth listening right through to the end just to hear him shout “Beeeeeeeitch.”
c) I really hope she was in the session at the time.

Score: 4/10


LFO“Life is Good (Feat. MOP)”


LFO were a pop/emo/boy-band monstrosity whose entire existence could have been to score big moments in Dawson’s Creek or that teen-movie with Kirsten Dunst and Sisqo in it. The ‘F’ in LFO stands for Fischetti.

MOP were and (still are) one of NYC’s pre-imminent underground blacking out crews who never recorded a song that wouldn’t start a mosh pit at the Tunnel, with deliveries so consistently amped up you can feel a fine mist of saliva coming right through the speakers.

It is possible that LFO were fans. It’s also possible that an A&R was absently scrolling down a spreadsheet of cheapest available guest rappers and the chance appearance of another acronym really jumped off the screen. It could be that there is no higher meaning or purpose to anything other than matter colliding at random in a cold, infinite void. If I close my eyes, I’m certain I can feel us all hurtling through space at 827,666 miles per hour as LFO weave a bittersweet song of experience where “life is good” and, paradoxically, “life is cruel.”

Right as I’m considering drawing a warm bath from where I’ll comfortably ingest all of the remaining Cocodamol, the voice of Billy Danz joyfully smashes me between the eyes with some characteristically bellicose lines about how trife it is in Brownsville. As it always is with M.O.P, the pain is visceral, and given the dire context of their rapping, strangely uplifting. I involuntarily surge with the blind optimism of the raped and ravaged old woman from Voltaire’s “Candide.” As Lil Fame bellows with gospel-soaked defiance, “Damn, life is real and so tragic.”

Score: 7/10 (7 to MOP, nothing to Fischetti)