The Best Dave Chappelle Movies 

Updated June 11, 2019 640 votes 216 voters 51.7k 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

Released: 1998

Directed by: Tamra Davis

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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#39 of 493 The Funniest '90s Movies #1,204 of 1,699 The Most Rewatchable Movies #198 of 1,208 The Absolute Funniest Movies Of All Time

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Neil Patrick Harris, Denise Richards, Dave Chappelle

Released: 2002

Directed by: Malcolm D. Lee

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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#137 of 726 The Best Black Movies Ever Made, Ranked #323 of 624 The Greatest Guilty Pleasure Movies #891 of 1,027 The All-Time Greatest Comedy Films

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Eddie Murphy, Jada Pinkett Smith, Dave Chappelle

Released: 1996

Directed by: Tom Shadyac

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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#42 of 726 The Best Black Movies Ever Made, Ranked #64 of 493 The Funniest '90s Movieslisted on Every Oscar Winning Film Ever

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Martin Lawrence, Dave Chappelle, Octavia Spencer

Released: 1999

Directed by: Les Mayfield

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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#129 of 726 The Best Black Movies Ever Made, Ranked #129 of 493 The Funniest '90s Movies #574 of 1,027 The All-Time Greatest Comedy Films

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Patrick Stewart, Mel Brooks, Dave Chappelle

Released: 1993

Directed by: Mel Brooks

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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Here's What The Cast Of Robin Hood: Men In Tights Looks Like Now #244 of 377 The Best Musical Movies of All Time #26 of 493 The Funniest '90s Movies

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Dave Chappelle, Albert Precourt

Released: 2000

Directed by: Stan Lathan

Dave Chappelle: Killin' Them Softly is a 2000 comedy documentary film written by Dave Chappelle and directed by Stan Lathan.
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Sarah Silverman, Danny DeVito, Dave Chappelle

Released: 2000

Directed by: Scott Alexander, Larry Karaszewski

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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Dave Chappelle, Greer Barnes

Released: 2004

Directed by: Stan Lathan

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
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Nicolas Cage, John Malkovich, Steve Buscemi

Released: 1997

Directed by: Simon West

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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#375 of 1,699 The Most Rewatchable Movies #21 of 624 The Greatest Guilty Pleasure Movies #168 of 548 The Greatest Movies for Guys

You've Got Mail is listed (or ranked) 10 on the list The Best Dave Chappelle Movies
Tom Hanks, Meg Ryan, Sara Ramirez

Released: 1998

Directed by: Nora Ephron

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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#195 of 493 The Funniest '90s Movies #241 of 1,699 The Most Rewatchable Movies #66 of 624 The Greatest Guilty Pleasure Movies

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Janice Dickinson, Dave Chappelle, Ron Jeremy

Released: 2007

Directed by: Perry Santos

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

Released: 2018

Directed by: Bradley Cooper

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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The Best Songs on the 'A Star Is Born' Soundtrack #232 of 377 The Best Musical Movies of All Timelisted on Every Oscar Winning Film Ever

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Common, Mos Def, Dave Chappelle

Released: 2006

Directed by: Michel Gondry

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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#225 of 726 The Best Black Movies Ever Made, Ranked #961 of 1,208 The Absolute Funniest Movies Of All Time #108 of 137 The Best Concert Movies

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LL Cool J, Jada Pinkett Smith, Dave Chappelle

Released: 1998

Directed by: Daisy von Scherler Mayer

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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Moby, Dave Chappelle, Bam Bam Bigelow

Released: 1996

Directed by: John Payson

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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Kate Hudson, Courtney Love, Ben Affleck

Released: 1999

Directed by: Risa Bramon Garcia

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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#28 of 35 The Best Period Movies Set in the '80s #57 of 58 The Best Teen Movies of the 1990s #26 of 61 The Best Paul Rudd Movies

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High Times Greatest Hits Snoop Dogg, Dave Chappelle, Redman

Released: 2009

Directed by: David Bienenstock

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Open Mic Dave Chappelle, Jim Breuer, Shawn Wayans

Released: 2000

Directed by: Jason Dudek

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Matthew Perry, Dave Chappelle, Calista Flockhart

Released: 1994

Directed by: Doug Liman

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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Jamie Foxx, LL Cool J, Dave Chappelle

Released: 2007

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Kathleen Turner, Dennis Quaid, Dave Chappelle

Released: 1993

Directed by: Herbert Ross

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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Kathleen Turner, Steve Buscemi, Christopher Lloyd

Released: 1997

Directed by: Tom DiCillo

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