Before he became one of the most fearless voices in comedy, Dave Chappelle was the guy who could steal a movie with a single scene. Long before Chappelle’s Show rewired sketch television, he was building a film résumé full of misfits, oddballs, and live wires that turned even the goofiest scripts into cult favorites.
What makes Chappelle’s film work endure isn’t just the humor but the chaos behind it. He has a way of shifting tone whenever he appears, walking into polished studio comedies and transforming them into something looser and more spontaneous. Whether he’s dropping conspiracy theories in a parody, roasting Eddie Murphy into oblivion, or philosophizing from behind a steering wheel, Chappelle never seems to fit neatly into someone else’s movie. Instead, he bends it toward his own brand of energy.
These nine performances capture that unpredictable side of his artistry. They showcase the moments when Chappelle’s wit, timing, and irreverence collided on-screen, and remind us that long before he owned the stage, he was already rewriting the rules of movie comedy.
1. Ahchoo — Robin Hood: Men in Tights
Chappelle’s film debut was a full-on comedy boot camp. Playing “Ahchoo” in Mel Brooks’ medieval parody, he marched into Sherwood Forest wearing a baseball cap, breaking the fourth wall, and injecting Hip Hop swagger into the Middle Ages. It’s silly, self-aware, and full of early hints of his sharp rhythm. Even surrounded by slapstick and sight gags, he made the movie feel like a test run for the confident humor that would define his career.
2. Thurgood Jenkins — Half Baked
Half Baked was the quintessential Chappelle experience on film — one part stoner fable, one part absurdist sketch. Co-written by Chappelle himself, the movie follows a group of friends raising bail money by selling weed, spiraling into cartoonish adventures and surreal cameos. Beneath all the smoke, it’s a sly commentary on friendship and freedom. It’s also the first time Chappelle got to fully build his own comic universe.
3. Rusty P. Hayes — Screwed
In Screwed, Chappelle plays Rusty, a hustler whose get-rich-quick scheme involves kidnapping a dog for ransom. The movie’s tone is all over the place, but Chappelle thrives in the madness. His jittery energy, fast-talking improvisation, and total lack of self-preservation turn every misstep into a laugh. Even in a film that few remember, he’s unforgettable.
4. Conspiracy Brother — Undercover Brother
It doesn’t get more over-the-top than this. As Conspiracy Brother, Chappelle became the living embodiment of online paranoia years before social media gave it a platform. He was a dashiki-wearing truth-teller who believed “The Man” controls everything from TV ads to condiment preferences. The performance was wild, fearless, and perfect for the satire of its time.
5. Reggie Warrington — The Nutty Professor
Chappelle’s cameo as Reggie, a ruthless stand-up comic, was one of the funniest takedowns ever filmed. His vicious roast of Eddie Murphy’s character in a nightclub scene was short but explosive — all ego and no empathy (also, Murphy’s eventual comeback). It was the kind of mean-spirited performance only a real comic could sell, and it showed how Chappelle can dominate a room with nothing but a mic and audacity.
6. Tulley — Blue Streak
Paired with Martin Lawrence, Chappelle turned what could’ve been a typical buddy role into pure chaos. Tulley was a loud, unpredictable sidekick whose mouth moved faster than his brain. His reactions and improvised one-liners transformed routine scenes into comedic improv jams. You get the sense Lawrence had to fight to stay in character... which was exactly the point.
7. Dave — 200 Cigarettes
This offbeat New Year’s Eve ensemble movie gave Chappelle a rare chance to slow down (but not too much). As a cab driver wandering through Manhattan, he played the story’s connective tissue, dropping philosophy between rides and acting as the film’s hazy conscience. It’s a smaller, stranger role that showed his ability to add soul to the absurd.
8. Kevin Jackson — You’ve Got Mail
Chappelle in a Nora Ephron rom-com sounded like a casting experiment, and somehow, it worked. As Tom Hanks’ grounded best friend, he (almost) played it straight. There was a glint in his delivery that undercut the film’s sweetness, like he knew he didn’t belong in this world but planned to enjoy the free coffee anyway. It’s one of those roles that’s weird precisely because it’s normal.
9. George “Noodles” Stone — A Star Is Born
Chappelle took a softer turn as Noodles, the longtime friend to Bradley Cooper’s fading rock star. It was a calm, grounded performance, yet even in stillness, his presence felt like a curveball. His monologue about settling down and finding peace hit differently coming from someone whose career thrived on disruption. It’s a reminder that Chappelle’s power isn’t just in the punchline, but the pause after it.