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The Best Dave Chappelle Movies

Updated June 11, 2019 1.0k votes 222 voters 52.0k 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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Robin Hood: Men in Tights
Patrick Stewart, Mel Brooks
Released: 1993
Directed by: Mel Brooks
Robin Hood: Men in Tights is a 1993 French-American musical adventure comedy film and a parody... more on Wikipedia
2
65
9
Dave Chappelle: Killin' Them Softly
Dave Chappelle, Albert Precourt
Released: 2000
Directed by: Stan Lathan
Dave Chappelle: Killin' Them Softly is a 2000 comedy documentary film written by Dave...
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55
6
Con Air
Nicolas Cage, John Malkovich
Released: 1997
Directed by: Simon West
Con Air is a 1997 American action film directed by Simon West and produced by Jerry... more on Wikipedia
More Con Air
14 Turbulent Behind-The-Scenes Stories From ‘Con Air’#1 of 20 20 Bad Movies That Are Actually Really Good
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65
15
Half Baked
Snoop Dogg, Jon Stewart
Released: 1998
Directed by: Tamra Davis
Half Baked is a 1998 American stoner comedy film starring Dave Chappelle, Jim Breuer, Harland... more on Wikipedia
More Half Baked
#10 of 204 The Best Drug Movies of All Time#45 of 252 The Funniest '90s Movies
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Dave Chappelle: For What It's Worth
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... more on Wikipedia
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59
12
Screwed
Sarah Silverman, Danny DeVito
Released: 2000
Directed by: Scott Alexander, Larry Karaszewski
Screwed is a 2000 American comedy film, written and directed by Scott Alexander and Larry... more on Wikipedia
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53
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You've Got Mail
Tom Hanks, Meg Ryan
Released: 1998
Directed by: Nora Ephron
You've Got Mail is a 1998 American romantic comedy-drama film directed by Nora Ephron,... more on Wikipedia
More You've Got Mail
#293 of 1,540 The Most Rewatchable Movies#2 of 125 The Greatest Date Movies of All Time

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51
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A Star Is Born
Bradley Cooper, Lady Gaga
Released: 2018
Directed by: Bradley Cooper
A Star Is Born is a 2018 American musical romantic drama film directed by Bradley Cooper. A... more on Wikipedia
More A Star Is Born
The Best Songs on the 'A Star Is Born' Soundtrack#190 of 206 Musical Movies With the Best Songs
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39
4
I'm Rick James
Janice Dickinson, Dave Chappelle
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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37
8
Dave Chappelle's Block Party
Common, Mos Def
Released: 2006
Directed by: Michel Gondry
Dave Chappelle's Block Party, also known as Block Party, is a 2005 documentary film hosted and... more on Wikipedia
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32
7
Woo
LL Cool J, Jada Pinkett Smith
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... more on Wikipedia
More Woo
#72 of 119 The Best R-Rated Sex Comedies#183 of 202 The Best R-Rated Comedies
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The Nutty Professor
Eddie Murphy, Jada Pinkett Smith
Released: 1996
Directed by: Tom Shadyac
The Nutty Professor is a 1996 American slapstick science-fiction comedy film directed by Tom... more on Wikipedia
More The Nutty Professor
#448 of 1,189 Every Oscar Winning Film Ever#75 of 629 The Best Black Movies Ever Made, Ranked
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34
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Undercover Brother
Eddie Griffin, Chris Kattan
Released: 2002
Directed by: Malcolm D. Lee
Undercover Brother is a 2002 American action comedy film starring Eddie Griffin and directed... more on Wikipedia
14
36
14
Joe's Apartment
Moby, Dave Chappelle
Released: 1996
Directed by: John Payson
Joe's Apartment is a 1996 musical-comedy film starring Jerry O'Connell and Megan Ward and the... more on Wikipedia
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26
6
200 Cigarettes
Kate Hudson, Courtney Love
Released: 1999
Directed by: Risa Bramon Garcia
200 Cigarettes is a 1999 American ensemble comedy film directed by Risa Bramon Garcia, and... more on Wikipedia
More 200 Cigarettes
#32 of 36 The Best Period Movies Set in the '80s#55 of 61 The Best Paul Rudd Movies
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Blue Streak
Martin Lawrence, Dave Chappelle
Released: 1999
Directed by: Les Mayfield
Blue Streak is a 1999 film, directed by Les Mayfield with Martin Lawrence. The director has... more on Wikipedia
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17
6
High Times Greatest Hits
Snoop Dogg, Dave Chappelle
Released: 2009
Directed by: David Bienenstock
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15
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Open Mic
Dave Chappelle, Jim Breuer
Released: 2000
Directed by: Jason Dudek
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12
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Getting In
Matthew Perry, Dave Chappelle
Released: 1994
Directed by: Doug Liman
Getting In, also known as Student Body, is a 1994 American comedy film directed by Doug Liman... more on Wikipedia
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14
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Beef IV
Jamie Foxx, LL Cool J
Released: 2007
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12
8
Undercover Blues
Kathleen Turner, Dennis Quaid
Released: 1993
Directed by: Herbert Ross
Undercover Blues is a 1993 comedy film about a family of secret agents, starring Kathleen... more on Wikipedia
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12
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The Real Blonde
Kathleen Turner, Steve Buscemi
Released: 1997
Directed by: Tom DiCillo
The Real Blonde is a 1998 movie directed and written by Tom DiCillo. It stars Matthew Modine,... more on Wikipedia

High Times Greatest Hits

Open Mic