As he proved with his stand-up and the brilliant sketch series Chappelle’s Show, Dave Chappelle is one of the funniest people on the planet. But he’s also popped up in a few movies, energizing the smallest cameo or carrying a whole comedy. With The Nutty Professor airing this month on IFC, we’re paying tribute to Dave Chappelle’s best big screen roles.
10. Rusty P. Hayes, Screwed
In this dark Norm MacDonald comedy, Dave’s Rusty P. Hayes helps a bedraggled chauffeur kidnap his rich employer’s yappy dog to earn a million dollar ransom. Naturally, things go hilariously wrong. Dave is never funnier than when faced with the idiocy of others, even when he enabled them every step of the way.
9. Kevin, You’ve Got Mail
Yep, there was a time (the ’90s) when Dave Chappelle was in a Tom Hanks/Meg Ryan movie. Not the place you’d picture him, but his character Kevin Jackson is on hand to help Tom and Meg get on with their lives and realize the obvious love between them.
8. Tulley, Blue Streak
Chappelle crams comedy into Tulley, the movie’s most unfortunate character. Tulley can’t quite get away from a double-crossing criminal out for revenge, a diamond-thief-turned-fake-policeman, and quite a lot of very real policemen.
7. Disco Cabbie, 200 Cigarettes
Set on New Year’s Eve of 1981 (but released in 1999), 200 Cigarettes features a “who’s who” of Clinton-era stars — everyone from Christina Ricci to Courtney Love — trying to make it in the big city. But Dave Chappelle’s Disco Cabbie isn’t struggling with anything. Disco Cabbie knows exactly who he is and where he’s going. With a character name like Disco Cabbie you don’t even need the rest of the script — just point the camera on Dave and let him go.
6. Pinball Parker, Con Air
Pinball Parker proves that his powers extend to getting everyone’s attention and bringing the house down even when that house is a heavily guarded plane full of convicted felons. Dave improvised most of his lines in this Nic Cage action flick, and they’re some of the best ones in the movie.
5. Reggie Warrington, The Nutty Professor
The first revenge taken by the jelly-Jekyll-to-high-fitness-Hyde transformation of Sherman Klump in The Nutty Professor is against Reggie Warrington, a brutal insult comic. And giving Chappelle cart blanche to be as evil as possible is comedy gold. Even his name is an insult, chosen to mock the director of an earlier movie Eddie Murphy had appeared in.
4. Ahchoo, Robin Hood: Men in Tights
Chappelle’s first film appearance as Ahchoo in the Mel Brooks comedy Robin Hood: Men in Tights demonstrated his ability to steal a scene from the movie’s stars, and hinted to his future greatness to come.
3. Morris, Chi-raq
Dave’s most recent film role was in Spike Lee’s satire about gang violence in Chicago. When the women of Chicago withhold sex from men involved in gang violence, Dave’s strip club owner character is devastated by the loss.
2. Conspiracy Brother, Undercover Brother
Undercover Brother is an underrated spoof of blaxploitation films, and Dave’s “Conspiracy Brother” adds to the hilarity on display. People turn to him and ask “Conspiracy Brother, what do you think?,” and the result is always amazing.
1. Thurgood Jenkins/Sir Smoke-a-Lot, Half Baked
While Thurgood Jenkins gets plenty of good lines, it’s Dave’s rapper character Sir Smoke-a-Lot that really allows him to let his comedy freak flag fly. We suspect Sir Smoke-a-Lot and Rick James are related.