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224 voters

The Best Dave Chappelle Movies

Updated June 11, 2019 1.0k votes 224 voters 52.2k views22 items

List RulesVote 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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    The Nutty Professor

    Eddie Murphy, Jada Pinkett Smith

    Released1996

    Directed byTom 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 good-hearted...  more

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  • 2
    73
    12

    Robin Hood: Men in Tights

    Patrick Stewart, Mel Brooks

    Released1993

    Directed byMel 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 Lewis,...  more

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  • 3
    61
    5

    Half Baked

    Snoop Dogg, Jon Stewart

    Released1998

    Directed byTamra 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 and Neal...  more

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    #348 of 440 The Best Movies Of The 1990s#50 of 252 The Funniest '90s Movies

  • 4
    63
    8

    Dave Chappelle: Killin' Them Softly

    Dave Chappelle, Albert Precourt

    Released2000

    Directed byStan Lathan

    Dave Chappelle: Killin' Them Softly is a 2000 comedy documentary film written by Dave Chappelle and directed by Stan Lathan....  more
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    54
    6

    Con Air

    Nicolas Cage, John Malkovich

    Released1997

    Directed bySimon 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 its...  more

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  • 6
    55
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    Dave Chappelle: For What It's Worth

    Dave Chappelle, Greer Barnes

    Released2004

    Directed byStan 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 2004, and...  more
  • 7
    59
    12

    Screwed

    Sarah Silverman, Danny DeVito

    Released2000

    Directed byScott 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, Sarah...  more
  • 8
    53
    8

    You've Got Mail

    Tom Hanks, Meg Ryan

    Released1998

    Directed byNora 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 by...  more

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    #42 of 783 The Greatest Chick Flicks Ever Made#306 of 1,506 The Most Rewatchable Movies

  • 9
    46
    7

    A Star Is Born

    Bradley Cooper, Lady Gaga

    Released2018

    Directed byBradley 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 personal...  more

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    38
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    I'm Rick James

    Janice Dickinson, Dave Chappelle

    Released2007

    Directed byPerry Santos

    I'm Rick James is a 2007 documentary film by Perry Santos from Shoreline Entertainment....  more
  • 11

    Released2006

    Directed byMichel 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
  • 12
    32
    6

    Woo

    LL Cool J, Jada Pinkett Smith

    Released1998

    Directed byDaisy 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....  more

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    #22 of 65 The Best Black Comedy Movies Of The '90s#159 of 225 The Best R-Rated Comedies

  • 13
    35
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    Joe's Apartment

    Moby, Dave Chappelle

    Released1996

    Directed byJohn 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
  • 14
    33
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    Undercover Brother

    Eddie Griffin, Chris Kattan

    Released2002

    Directed byMalcolm 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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    #823 of 924 The All-Time Greatest Comedy Films#453 of 456 The Most Quotable Movies Of All Time

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    200 Cigarettes

    Kate Hudson, Courtney Love

    Released1999

    Directed byRisa 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 Year's...  more

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  • 16
    26
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    Blue Streak

    Martin Lawrence, Dave Chappelle

    Released1999

    Directed byLes 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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    #35 of 57 The Funniest Movies About Cops#30 of 85 The Funniest Crime Parodies and Spoof Movies, Ranked

  • 17
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    High Times Greatest Hits

    Snoop Dogg, Dave Chappelle

    Released2009

    Directed byDavid Bienenstock

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    14
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    Open Mic

    Dave Chappelle, Jim Breuer

    Released2000

    Directed byJason Dudek

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    12
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    Getting In

    Matthew Perry, Dave Chappelle

    Released1994

    Directed byDoug Liman

    Getting In, also known as Student Body, is a 1994 American comedy film directed by Doug Liman starring Andrew McCarthy and Stephen Mailer....  more
  • 20
    12
    6

    The Real Blonde

    Kathleen Turner, Steve Buscemi

    Released1997

    Directed byTom 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 entertainment...  more
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    14
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    Beef IV

    Jamie Foxx, LL Cool J

    Released2007

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    12
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    Undercover Blues

    Kathleen Turner, Dennis Quaid

    Released1993

    Directed byHerbert 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....  more