Just Rankin’ Sh!t

Dave Chappelle’s 5 Best Film Roles, Ranked

The comic’s big-screen turns that paved the way for ‘Chappelle’s Show’

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Published in
2 min readJan 26, 2021

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Photo illustration; image source: Tim Mosenfelder/Getty Images

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5. “Robin Hood: Men in Tights”

In Chappelle’s coming-out party, he plays Robin Hood’s sidekick — who just so happens to rock Reebok Pumps and drop a Malcolm X impression, just for the hell of it. Not bad for a 19-year-old.

4. “Undercover Brother”

Legend has it that Chappelle ad-libbed most of his lines as Conspiracy Brother while shooting this one. Huge, if true, because every quip he drops in Eddie Griffin’s magnum opus lands real-life LOLs. (Whatever happened to Eddie Griffin, anyway?)

3. “Blue Streak”

Come for two legends — Chappelle and Martin — tossing each other alley-oops like Bron and D. Wade in this heist flick turned cop comedy. Stay for Dave’s take on Wu-Tang’s methods of torture skit: “I’ll rip your lips off and kiss my ass with them shits… I’ll rip your tongue out and lick my balls with ‘em!”

2. “Nutty Professor”

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