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 Lawrence—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
For many of us, this was our first time seeing Chappelle do stand-up, playing Reggie Warrington, who is basically a more petulant version of himself. He and Eddie Murphy playing the dozens (“Boy’s ass is so fat, he’s got more crack than Harlem!”) is the stuff of yo mama joke legend.
You just knew this would be at the top of the stack. If you’ve ever smoked marijuana, eaten an edible, been in the vicinity of a bong, or pulled a weed from your front lawn, you’re familiar with this stoner classic — a masterwork of goofiness that created a blueprint for Chappelle’s Show, word to Sampson Simpson.
Read more: The 7 Best Hip-Hop Biopics, Ranked