The rap game is full of clowns you say? Sure, there are some jokers out there, but what about the dudes who are actually funny on purpose? My gut reaction would be to say Biz Markie, but what about the other comedic MC’s out there? Apologies to Blowfly and Bobby Jimmy & The Critters fans, YouTube failed you.

Beastie Boys

The Beasties have been making funny shit since ‘Cookie Puss’. Willingness to wear wigs in videos is a huge plus.

Humpty Hump/Shock G (Digital Underground)

Early record ‘Underwater Rhymes’ was hilarious…if you were six. ‘Humpty Dance’ was a great party record, but the character himself was basically Shock wearing a fur hat, plaid sports jacket and a classic novelty glasses/nose combo. Worth a chuckle? Sure, why not. Pure hilarity? Not so much.

Redman

Combined with Meth, he’s rap’s answer to Cheech & Chong. The Funk Doctor Spock gets extra points for being able to balance the prankster image along with being a respected rapper dude.

Prince Paul

The twisted mind behind De La Soul, Handsome Boy Modeling School and a bunch of other weird concept albums has been responsible for some pretty funny skits over the years (the De La Soul Is Dead stuff in particular), but his ‘wacky’ brand of satire can be hit and miss.

Will Smith aka The Fresh Prince

Before his TV Show, Will had carved out his lane as the ‘zany rap guy’ as seen in ‘hilarious’ videos such as ‘Parents Just Don’t Understand’ and ‘Girls Ain’t Nothin’ But Trouble’. Harmless fun, but hardly side-splitting stuff. As for his movie career, I guess Wild Wild West was a big joke…

J-Zone

This dude is a huge fan of ignorant rap, and a lot of his records such as the Boss Hogg Barbarians LP are tributes to that old Rap-A-Lot sound. Not as funny as actually bumping Geto Boys and Gangster NIP, but still good value. The song he made about getting a rash from rocking a fake gold rope is priceless.

50 Cent

Curtis’ constant WWF-style conflicts are usually pretty entertaining. When you’re rich and bored, you end up doing some way-out shit, as witnessed by his recent campaign against Rick Ross. As for the ‘Piggy Bank’ video, I’m not sure what’s funnier – the Nas character, Jada as Ninja Turtle or just the fuckin’ ugly computer graphics of the clip.

Eminem

Who could ever tire of Slim Shady making fun of D-List celebrities? Everybody except readers of TMZ? Oh, OK. What about his ‘crazy mental dude’ stuff? That too, huh?

Bizarre from D-12

If fat guys wearing shower caps and rapping badly is your idea of a good belly laugh…step right up.

Cam’Ron

If you haven’t heard Crime Pays yet, you’re missing out on the Lenny Bruce of rap. No to mention that the Killa Season movie is pure gold.

MC Paul Barman

A Jewish nerd rapper who’s wack on purpose? Meh.

Mighty Casey

A remake of ‘White Lines’ about bangin’ pale broads? Approved!

The Lonely Island

A couple of crackers doing musical parodies? It’s crazy, but it just might work! ‘I’m On A Boat’ was good, but this is better….

Flight of The Conchords

More white dudes, but from New Zealand, which is funnier by default (sorta like Canadians).

Biz Markie

Ah, fuck it. Biz is still the king of hip-hop comedy. ‘Pickin’ Boogers’ and ‘Just A Friend’ are classic comedy by themselves, but when combined with his rendition of ‘Benny & The Jets’, it’s a flawless victory.

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Who did I miss that you wanna see in part 2?