The Fertile Comic Grounds of Gangsta Rap

Rap and comedy make strange bedfellows — just ask Insane Clown Posse. But the impending release of Aziz Ansari’s mixtape reminded us of just how funny the rap-comedy genre can be when you’re actually laughing with the artist. We’ve only heard one track so far from the Raaaaaaaandy/Dave Sitek project, but it was enough for us to compile a quick list of some of our favorite rap-comedy collaborations, tongue firmly planted in cheek. After the jump, read and watch what happens when the musical sensibilities of Tupac clash with unabashed satire. Let us know which ones are your favorites.

“Aaaaaaaangry” – Aziz Ansari as Raaaaaaaandy, with Dave Sitek.

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If Raaaaaaaandy wasn’t the one laying down the gauntlet, Dave Sitek could probably have a fruitful career producing predictably pompous radio rap for less-aware rappers. Randy calls out Jay-Z for his Coldplay collaborations, makes fun of Kid Cudi for smoking pot alone, and forgets that Wu-Tang Clan ain’t nothing to fuck with. He also finds time for a credible Eminem impression and a stinging, accurate jab at Dr. Dre’s stagnant creative output. The album tagline is “Busting a nut on your pillow, Feburary 2010,” and the duo looks dead serious. “Where your verses at?” is worthy of becoming the pejorative equivalent of “get your shit together.”

“I’m On a Boat” – The Lonely Island feat. T-Pain

The undisputed titan of the genre, surprisingly catchy and hilariously profane. T-Pain is decidedly nonchalant when he is chosen to join Samberg and Co. on the boat, making the actions that ensue seem even more ridiculous. A nautical-themed pashmina afghan makes an appearance, as does as an inflatable dolphin and a desire to fly the boat to the moon. The Lonely Island’s considerable musical oeuvre is rounded out by the equally immortal “Jizz In My Pants.” Can you believe that “I’m On a Boat” hit #1 on iTunes and was nominated for a non-comedy album Grammys?

“Natalie’s Rap” (Saturday Night Live) – Natalie Portman

Picture Queen Amidala busting out gats to mow down Imperial guards in a trans-galactic drive-by shooting. The image isn’t too unbelievable when watching Natalie Portman satirize her image as a foul-mouthed, hard-as-nails street gangster. A profane Portman spitfires through exclamations like “I’ll watch you laugh and cry/while I laugh you die.” She nails the chest-thumping theatrics and posturing found in many gangster-rap videos, accompanied alternately by a glowering posse and a shimmying Andy Samberg providing back up vocals in a Viking costume. This also might just be Conan O’ Brien’s new favorite rap song, considering Portman manages to rhyme “motherfucker” with “Jeff Zucker.”

“Empire State of Mind” – Alicia Keys and Stephen Colbert

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Although not a full-on collaboration, Stephen Colbert added guest verses to Alicia Key’s performance on his talk show, altering Jay-Z’s lyrics for a less rhapsodic treatment of New York City. Colbert’s verse, delivered in a too-tight hoodie shadowing his face, centers around him moving to Connecticut because the air quality minimizes his asthma. Colbert’s nostalgia for the appetizer deal at the Hard Rock Cafe is about as far as someone can get from selling rock on the corner in of Marcy Avenue. Colbert also snaps and twirls like he’s in a Sinatra-era big bad jazz club, and it’s to Key’s credit that she looks to be wholeheartedly enjoying the entire performance.

“Impregn8ed” – Jimmy Kimmel and Tracy Morgan

Jimmy Kimmel once formed the backbone of a Snoop Dogg beat by farting into a microphone, and anyone familiar with 30 Rock probably remembers cringing over Tracy Morgan’s character attempting to rap about fat-necked girls. Here the two duet on “Impregn8ed,” taking the R. Kelly paradigm one step further by making pregnancy the only acceptable outcome of a night spent clubbing. It’s billed as “Tray-Mo featuring Lil’ Jim,” with Kimmel rocking dreadlocks and gold grilles while singing the Auto-tuned chorus, which rhymes “impregnated” with “ovulated.” Morgan miraculously manages to keep his shirt on but actually seems legitimately worried when he spots a girl whose “tummy’s too tight.” Now that we’re on the subject, how entertaining would a Tray-Mo vs. Raaaaaaaandy beef be?