The 5 most unintentionally hilarious moments in hip-hop

Doc Brown is a rapper turned comedian who performed alongside Amy Winehouse and Lily Allen as part of Mark Ronson’s live shows before focusing on comedy and appearing on The Inbetweeners, Russell Howard’s Good News, and Ricky Gervais’ Derek. He also happens to be novelist Zadie Smith’s younger brother. Ahead of his “Of Mic and Men” shows at the Melbourne Comedy Festival, Brown combined his trades for FL to highlight five unintentionally hilarious moments in hip-hop.

5. A$AP Rocky is truly an enlightened being

There was a hilariously awkward moment at the MTV Video Awards last year when A$AP Rocky was paired with gay basketball player Jason Collins to honour rapper Macklemore and speak out against homophobia in black music. Collins gave what was clearly a very difficult public speech for him, baring his heart and soul to the world and pleading for respect. The bravery was self-evident. What perfect timing then for Harlem’s self proclaimed “Pretty Motherfucker” to step into the void and basically say “Yeah gays is all good and shit, whatever” and proceed to plug his next releases. yes, with dates and everything. Thanks Rock.

4. Canibus’ career ends on camera

More on the cringetastic/tragi-nightmare end of the comedy spectrum, this was the moment a true great not only dug his own grave, but very politely threw his own carcass into it and helpfully proceeded to scoop six feet of graveyard earth over his own face. Former heavyweight lyricist Canibus was revered in the late ‘90s as a kind of rappers’ rapper – the man who could rhyme for days with sharp and complex similies and metaphors. The man who famously buried LL Cool J on the instant classic battle rap opus ‘Second Round Knockout’. Suddenly here we witness a very small and arrogant little man with one little arm inexplicably in a little sling, being torn apart by a white kid called Dizaster at an underground battle comp. Look out for the truly Gervais-like moment when the fallen hero actually draws on lyrics from a notepad from his 16-year-old greatest hit. Sheesh.

3. Kanye’s Zane Lowe interview

Now, technically Kanye could and perhaps even should be the subject of each spot on this Top 5. There really are so many moments to choose. Who can forget when he bumped his head on a street sign and got angry when a paparazzo checked if he was okay? The ‘Bound 2’ video? The Leather Kilt? The Mike Myers moment? His explosion on Sway’s Breakfast Show is particulary memorable – when having had his opinion questioned he screamed “YOU AINT GOT THE ANSWERS SWAY!” A phrase I still inexplicably shout at people to this day. But watching him get worked up about fashion houses refusing to buy his “leather jogging pants” design always tickles me. Yes Yeezy, it could have been racism, but it could also have been the fact that they were leather jogging pants.


2. P Diddy: Unforgivable

Popstars with fragrance lines are nothing new, but something about the advert for Sean “Diddy” Combs’ perfume for women really tickles me. Perhaps it’s the distinct lack of chemistry between Combs and his onscreen “love” with whom he is supposed to be obsessed; maybe it’s the shades he dons in the darkest of nighttime alleyways whilst sharing intense eye contact; hey, maybe it’s just Sean acting. One thing is certain – everything about this advert was nailed by Sean in one word before the camera even started rolling: Unforgivable.

1. LL Cool J and Brad Paisley’s ‘Accidental Racist’

Finally, If you’re yet to see LL Cool J and country singer Brad Paisley’s 2013 oddity, Accidental Racist, steel yourself for the heavyweight champ of unintentional hip-hop humour. This should really be called ‘Accidental Lolfest’. With countless lyrical gems such as the “If you don’t judge my gold chains, I’ll forget the iron chains”, it appears that the conclusion is – “hey come on, slavery was a bit annoying but so’s all sorts of stuff- like you not liking my cowboy hat or LL’s bizarre octagon shaped head”. What Cool James Todd was thinking when he wrote “RIP Robert E. Lee but I’ve gotta thank Abraham Lincoln for freeing me, know what I mean” the Gods of Rap only know.

Doc Brown will be appearing at the Melbourne Comedy Festival from March 27 until April 20 (except Mondays) in the Victoria Hotel’s Banquet Room. Check out the festival website for more details.