Every time we have any form of a "Greatest Rapper" discussion, I try to look for commonalities—what do they all have in common?
For example, as OmeroDaPharaoh recently pointed out, having an "m" in your name greatly increases your chances of success. In addition, I think I've found another commonality—a sense of humor. Almost every rapper on any conceivable top 10 greatest rappers of all-time list has the ability to both drop some murderous rhymes and make you laugh, it can't be a coincidence. But who's the Funniest Rapper of All-Time?
Sounds like a perfect new Question of the Week.
As I've thought it over, just like you've got different styles of comedians, you've got different styles of rap comedians. Will Ferrell is funny for a different reason than Chris Rock is funny who's funny for a different reason than Chris Farley. How do you weigh which one if the "funniest"? I'm not sure, we'll have to debate it out, but it's a good way to organize some of the candidates.
Frankly, the first name that comes to mind is Kanye. While the humor seems to have largely faded from his music, there aren't many who can turn out a classic comic punchline better than Ye. "Got a dark skin girl look like Michael Jackson, got a light skin girl look like Michael Jackson," alone puts him in the pantheon. Actually, one the classic joke set-up punchline tip, Eminem has to also be in the conversation. Never forget, he made his name off being funny. I'd also include Childish Gambino and Wax in this more punchline-driven category, although I don't think they can really fuck with Kanye or Em comedically (somewhat ironic considering Gambino's actually a comic).
The second school of comic rappers is what I'm going to call the Will Ferrell school; they're funny because they're able to balance absurdity without being completely insane. The leader of this school has to be Ghostface Killah; he's able to push things to an almost surreal territory without going completely overboard. Case in point, "I got soccer moms paying for cock. Asians get it from behind while they cleanin their wok." And if we're talking Ghost, we'll also have to bring up Action, who's funny for the exact same reason, and I'd also throw Danny Brown in here:
And the last school is the Chris Farley school, rappers who are funny because they're so completely, insanely over the top. That's really a school that's exploded in recent years, including a new sub-category of rappers whose schtick is being as comedically hilarious as possible. These are the rappers who are the most openly actual comics: I'm throwing 2 Chainz, Riff Raff, Lil B etc. into this group:
Ultimately, I have to go with Kanye. We can have a thousand qualifications and discussions, but really it comes down to "who makes you laugh the most," and as much as I love Ghost, no one's made me laugh more than Kanye over the years.
So who you got?