The Best Dave Chappelle Movies 

640 votes 216 voters 51.5k views 22 items

List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Dave Chappelle movies, ranked best to worst with movie trailers when available. Dave Chappelle's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Dave Chappelle movies is decided by how many votes they receive, so only highly rated Dave Chappelle movies will be at the top of the list. Dave Chappelle has been in a lot of films, so people often debate each other over what the greatest Dave Chappelle movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Dave Chappelle films to end the squabble once and for all.

If you think the best Dave Chappelle role isn't at the top, then upvote it so it has the chance to become number one. The greatest Dave Chappelle performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

This list features films like The Nutty Professor and The Real Blonde.

"This list answers the questions, "What are the best Dave Chappelle movies?" and "What are the greatest Dave Chappelle roles of all time?"
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Snoop Dogg, Jon Stewart, Willie Nelson
Half Baked is a 1998 American stoner comedy film starring Dave Chappelle, Jim Breuer, Harland Williams and Guillermo Díaz. The film was directed by Tamra Davis, co-written by Chappelle ...more

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#320 of 1,007 The All-Time Greatest Comedy Films #219 of 1,198 The Absolute Funniest Movies Of All Time

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Neil Patrick Harris, Denise Richards, Dave Chappelle
Undercover Brother is a 2002 American action comedy film starring Eddie Griffin and directed by Malcolm D. Lee. The screenplay is by Michael McCullers and co-executive producer John Ridley, who ...more

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#128 of 720 The Best Black Movies Ever Made, Ranked #699 of 1,007 The All-Time Greatest Comedy Films #389 of 625 The Greatest Guilty Pleasure Movies

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Eddie Murphy, Jada Pinkett Smith, Dave Chappelle
The Nutty Professor is a 1996 American slapstick science-fiction comedy film directed by Tom Shadyac, and a remake of the 1963 film, which starred Jerry Lewis. Grossly overweight yet ...more

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#15 of 720 The Best Black Movies Ever Made, Ranked #248 of 302 The Greatest Soundtracks of All Timelisted on Every Oscar Winning Film Ever

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Martin Lawrence, Dave Chappelle, Octavia Spencer
Blue Streak is a 1999 film, directed by Les Mayfield with Martin Lawrence. The director has also directed other famous films, including the remake of Miracle on Thirty-fourth Street in 1994. In ...more

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#214 of 720 The Best Black Movies Ever Made, Ranked #567 of 1,007 The All-Time Greatest Comedy Films #16 of 84 The Funniest Black Movies Ever Made

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Patrick Stewart, Mel Brooks, Dave Chappelle
Robin Hood: Men in Tights is a 1993 French-American musical adventure comedy film and a parody of the Robin Hood story. Produced and directed by Mel Brooks, the film stars Cary Elwes, Richard ...more

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#229 of 371 The Best Musical Movies of All Time #119 of 1,699 The Most Rewatchable Moviesfeaturing Here's What The Cast Of Robin Hood: Men In Tights Looks Like Now

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Dave Chappelle, Albert Precourt
Dave Chappelle: Killin' Them Softly is a 2000 comedy documentary film written by Dave Chappelle and directed by Stan Lathan.
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Nicolas Cage, John Malkovich, Steve Buscemi
Con Air is a 1997 American action film directed by Simon West and produced by Jerry Bruckheimer, producer of The Rock. It stars Nicolas Cage, John Cusack, and John Malkovich. The film borrows ...more

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#172 of 460 The Most Quotable Movies of All Time #153 of 548 The Greatest Movies for Guys

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Dave Chappelle, Greer Barnes
Dave Chappelle: For What It's Worth is a 2004 television special starring stand-up comedian Dave Chappelle. The performance was recorded at The Fillmore in San Francisco, California in June ...more
You've Got Mail is listed (or ranked) 9 on the list The Best Dave Chappelle Movies
Tom Hanks, Meg Ryan, Sara Ramirez
You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron, starring Tom Hanks and Meg Ryan. It was written by Nora and Delia Ephron based on the 1937 play Parfumerie ...more

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#411 of 1,699 The Most Rewatchable Movies #100 of 625 The Greatest Guilty Pleasure Movies #103 of 324 Movies with the Best Soundtracks

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Sarah Silverman, Danny DeVito, Dave Chappelle
Screwed is a 2000 American comedy film, written and directed by Scott Alexander and Larry Karaszewski. It stars Norm Macdonald, Dave Chappelle, Danny DeVito, Elaine Stritch, Daniel Benzali, ...more
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Janice Dickinson, Dave Chappelle, Ron Jeremy
I'm Rick James is a 2007 documentary film by Perry Santos from Shoreline Entertainment.
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Bradley Cooper, Lady Gaga, Sam Elliott
A Star Is Born is a 2018 American musical romantic drama film directed by Bradley Cooper. A movie star (Cooper) helps a young singer/actress (Stefani Germanotta) find fame, even as age and ...more

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#247 of 371 The Best Musical Movies of All Timefeaturing The Best Songs on the 'A Star Is Born' Soundtracklisted on Every Oscar Winning Film Ever

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Common, Mos Def, Dave Chappelle
Dave Chappelle's Block Party, also known as Block Party, is a 2005 documentary film hosted and written by comedian Dave Chappelle, and directed by Michel Gondry. Its format is inspired by the ...more
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LL Cool J, Jada Pinkett Smith, Dave Chappelle
Woo is a 1998 romantic comedy film, directed by Daisy V.S. Mayer, and starring Jada Pinkett Smith in the title role. Tommy Davidson co-stars. Woo was filmed in 1996.

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#250 of 720 The Best Black Movies Ever Made, Ranked #22 of 31 The Best Black Comedy Movies of the '90s

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Kate Hudson, Courtney Love, Ben Affleck
200 Cigarettes is a 1999 American ensemble comedy film directed by Risa Bramon Garcia, and written by Shana Larsen. The film is a mosaic following multiple characters in New York City on New ...more

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#27 of 34 The Best Period Movies Set in the '80s #56 of 58 The Best Teen Movies of the 1990s

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Moby, Dave Chappelle, Bam Bam Bigelow
Joe's Apartment is a 1996 musical-comedy film starring Jerry O'Connell and Megan Ward and the first film produced by MTV Films. It was based on a 1992 short film first made for MTV. The film was ...more
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High Times Greatest Hits
Snoop Dogg, Dave Chappelle, Redman
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Open Mic
Dave Chappelle, Jim Breuer, Shawn Wayans
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Matthew Perry, Dave Chappelle, Calista Flockhart
Getting In, also known as Student Body, is a 1994 American comedy film directed by Doug Liman starring Andrew McCarthy and Stephen Mailer.
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Kathleen Turner, Dennis Quaid, Dave Chappelle
Undercover Blues is a 1993 comedy film about a family of secret agents, starring Kathleen Turner and Dennis Quaid. The film was written by Ian Abrams and directed by Herbert Ross.
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Jamie Foxx, LL Cool J, Dave Chappelle
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Kathleen Turner, Steve Buscemi, Christopher Lloyd
The Real Blonde is a 1998 movie directed and written by Tom DiCillo. It stars Matthew Modine, Catherine Keener, and Maxwell Caulfield. The film is a satire on New York's fashion and ...more