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The Funniest People in the World of Hip Hop

We’re not sure what to think about the news that Oakland-based Amy Winehouse lookalike and cinematographer Kreayshawn’s novelty hip hop parody “Gucci Gucci” — which has had about 2.5 million views since it was uploaded to YouTube — has landed her a deal with Columbia Records. As one YouTube commenter points out, it means that we’d better get used to her, but it’s also got us thinking about the dearth of genuinely funny hip hop out there. We’re not talking about comedy/novelty stuff — more the sharp rhymes that used to be the hallmark of the genre but now are harder and harder to find. Or maybe we’re just too old school for our own good sometimes. Either way, there are still some genuinely funny and witty rappers out there. We’ve selected five of our faves after the jump.

Beastie Boys

The obvious choices, perhaps, but the Beastie Boys have outgrown the frat-bro silliness of License to Ill and evolved into lyricists who manage to be genuinely funny while rarely being contrived or relying on juvenile gross-out humor. Who else, for instance, would ever boast that they “got more rhymes than Carl Sagan’s got turtlenecks”?

Snoop Dogg

Over the years, Snoop’s once very genuine sense of menace (remember the controversy Doggystyle caused on its release?) has mellowed into a cleverly constructed persona that’s part weed-smokin’ self-parody and part hip-hop elder statesman. These days, the most appealing thing about him is that he doesn’t take himself overly seriously, a rare thing in the ultra-macho world of hip hop and a particularly unlikely quality in a former Death Row employee. But, of course, he’s the one laughing — all the way to the bank. (Oh, and while we weren’t necessarily big fans of all the jokes he cracked during his performance at Comedy Central’s Trump Roast a couple of months back, we adored his put-down of Donald Trump himself: “I hear you want to run for president. Why not? It wouldn’t be the first time you’ve pushed a black family out of their home.”)

Mos Def

OK, so we mentioned this last time we rounded up funny musicians. But Mos is a genuinely funny guy — particularly his best moments on Chapelle’s Show.

Flavor Flav

When Public Enemy first appeared to terrify conservative talk-show hosts, they cut a remarkable image: two angry men in baseball hats and LA Raiders jackets, three black-clad dudes in sunglasses who looked like they were in some sort of paramilitary organization… and an outlandish skinny jester with gold teeth and an oversized clock around his neck. In the group’s glory days, Flav’s frequently hilarious interjections provided much-needed color and comic relief to Public Enemy’s records and performances, preventing them from becoming overwhelmingly polemic. In later years, he’s sullied his legacy somewhat with Flavor of Love, but remains a larger-than-life personality and one of the world’s great originals.

Ludacris

“Humor in hip-hop is important to me because I feel like I like to laugh and I love watching comedies so of course it comes through in my music,” Ludacris told ArtistDirect a while back. He’s not wrong – who else, for instance, would create an entire track based around retelling the story of an Eddie Murphy movie? He’s also got a way with a one-liner (like Word of Mouf‘s memorable description of women like “real life Scratch-n-Sniff stickers”).

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