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The Best Dave Chappelle Movies

Updated June 11, 2019 1.0k votes 221 voters 51.9k 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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  • 1
    Robin Hood: Men in Tights is listed (or ranked) 1 on the list The Best Dave Chappelle Movies
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    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... more on Wikipedia
  • 2
    Dave Chappelle: Killin' Them S is listed (or ranked) 2 on the list The Best Dave Chappelle Movies
    65
    9

    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...
  • 3
    Con Air is listed (or ranked) 3 on the list The Best Dave Chappelle Movies
    55
    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... more on Wikipedia

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  • 4
    Half Baked is listed (or ranked) 4 on the list The Best Dave Chappelle Movies
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    15

    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... more on Wikipedia
  • 5
    Dave Chappelle: For What It's  is listed (or ranked) 5 on the list The Best Dave Chappelle Movies
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    8

    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... more on Wikipedia
  • 6
    Screwed is listed (or ranked) 6 on the list The Best Dave Chappelle Movies
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    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... more on Wikipedia
  • 7
    You've Got Mail is listed (or ranked) 7 on the list The Best Dave Chappelle Movies
    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,... more on Wikipedia

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    #253 of 1,647 The Most Rewatchable Movies#18 of 84 Great Movies That Take Place in Autumn

  • 8
    A Star Is Born is listed (or ranked) 8 on the list The Best Dave Chappelle Movies
    51
    8

    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... more on Wikipedia

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    The Best Songs on the 'A Star Is Born' Soundtrack#240 of 373 The Best Musical Movies Of All Time

  • 9
    I'm Rick James is listed (or ranked) 9 on the list The Best Dave Chappelle Movies
    39
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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.
  • 10
    Dave Chappelle's Block Party is listed (or ranked) 10 on the list The Best Dave Chappelle Movies

    Released2006

    Directed byMichel Gondry

    Dave Chappelle's Block Party, also known as Block Party, is a 2005 documentary film hosted and... more on Wikipedia
  • 11
    Woo is listed (or ranked) 11 on the list The Best Dave Chappelle Movies
    32
    7

    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... more on Wikipedia

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    #72 of 119 The Best R-Rated Sex Comedies#183 of 202 The Best R-Rated Comedies

  • 12
    The Nutty Professor is listed (or ranked) 12 on the list The Best Dave Chappelle Movies
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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... more on Wikipedia

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    #448 of 1,189 Every Oscar Winning Film Ever#228 of 1,137 The Absolute Funniest Movies Of All Time

  • 13
    Undercover Brother is listed (or ranked) 13 on the list The Best Dave Chappelle Movies
    34
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    Undercover Brother

    Neil Patrick Harris, Denise Richards

    Released2002

    Directed byMalcolm D. Lee

    Undercover Brother is a 2002 American action comedy film starring Eddie Griffin and directed... more on Wikipedia

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    #843 of 922 The All-Time Greatest Comedy Films#290 of 560 The Greatest Guilty Pleasure Movies

  • 14
    Joe's Apartment is listed (or ranked) 14 on the list The Best Dave Chappelle Movies
    36
    14

    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... more on Wikipedia
  • 15
    200 Cigarettes is listed (or ranked) 15 on the list The Best Dave Chappelle Movies
    26
    6

    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... more on Wikipedia

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  • 16
    Blue Streak is listed (or ranked) 16 on the list The Best Dave Chappelle Movies
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    15

    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... more on Wikipedia
  • 17
    High Times Greatest Hits is listed (or ranked) 17 on the list The Best Dave Chappelle Movies
    17
    6

    High Times Greatest Hits

    Snoop Dogg, Dave Chappelle

    Released2009

    Directed byDavid Bienenstock

  • 18
    Open Mic is listed (or ranked) 18 on the list The Best Dave Chappelle Movies
    15
    6

    Open Mic

    Dave Chappelle, Jim Breuer

    Released2000

    Directed byJason Dudek

  • 19
    Getting In is listed (or ranked) 19 on the list The Best Dave Chappelle Movies
    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... more on Wikipedia
  • 20
    Beef IV is listed (or ranked) 20 on the list The Best Dave Chappelle Movies
    14
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    Beef IV

    Jamie Foxx, LL Cool J

    Released2007

  • 21
    Undercover Blues is listed (or ranked) 21 on the list The Best Dave Chappelle Movies
    12
    8

    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... more on Wikipedia
  • 22
    The Real Blonde is listed (or ranked) 22 on the list The Best Dave Chappelle Movies
    12
    14

    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,... more on Wikipedia
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