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The Best Chris Penn Movies

Updated September 23, 2019 476 votes 71 voters 7.3k views41 items

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

List of the best Chris Penn movies, ranked best to worst with movie trailers when available. Chris Penn'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 Chris Penn movies is decided by how many votes they receive, so only highly rated Chris Penn movies will be at the top of the list. Chris Penn has been in a lot of films, so people often debate each other over what the greatest Chris Penn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Chris Penn films to end the squabble once and for all.

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

This list is made up of a variety of films, including Kiss Kiss and The Funeral.

"This list answers the questions, "What are the best Chris Penn movies?" and "What are the greatest Chris Penn roles of all time?"

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  • 1
    Reservoir Dogs is listed (or ranked) 1 on the list The Best Chris Penn Movies
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    Reservoir Dogs

    Quentin Tarantino, Steve Buscemi

    Released1992

    Directed byQuentin Tarantino

    Reservoir Dogs is a 1992 American ensemble crime film that depicts the events before and after... more on Wikipedia

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    #219 of 1,647 The Most Rewatchable Movies#66 of 149 Movies That Should Never Be Remade

  • 2
    Footloose is listed (or ranked) 2 on the list The Best Chris Penn Movies
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    Footloose

    Sarah Jessica Parker, Kevin Bacon

    Released1984

    Directed byHerbert Ross

    Footloose is a 1984 American musical-drama directed by Herbert Ross. It tells the story of Ren... more on Wikipedia
  • 3
    Pale Rider is listed (or ranked) 3 on the list The Best Chris Penn Movies
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    Pale Rider

    Clint Eastwood, Chris Penn

    Released1985

    Directed byClint Eastwood

    Pale Rider is a 1985 American western film produced and directed by Clint Eastwood, who also... more on Wikipedia

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    #11 of 399 The Best Western Movies Ever Made#146 of 522 The Greatest Movies Of The 1980s, Ranked

  • 4
    At Close Range is listed (or ranked) 4 on the list The Best Chris Penn Movies
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    At Close Range

    Sean Penn, Christopher Walken

    Released1986

    Directed byJames Foley

    At Close Range is a 1986 crime drama film directed by James Foley, based on the real life... more on Wikipedia
  • 5
    True Romance is listed (or ranked) 5 on the list The Best Chris Penn Movies
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    True Romance

    Brad Pitt, Val Kilmer

    Released1993

    Directed byTony Scott

    True Romance is a 1993 American film directed by Tony Scott and written by Quentin Tarantino.... more on Wikipedia

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    #56 of 204 The Best Drug Movies of All Time#24 of 108 The Best Mafia Films Of All Time

  • 6
    To Wong Foo, Thanks for Everyt is listed (or ranked) 6 on the list The Best Chris Penn Movies
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    Released1995

    Directed byBeeban Kidron

    To Wong Foo, Thanks for Everything! Julie Newmar is a 1995 American comedy film, starring... more on Wikipedia

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    #159 of 252 The Funniest '90s Movies#759 of 836 The Greatest Chick Flicks Ever Made

  • 7
    All the Right Moves is listed (or ranked) 7 on the list The Best Chris Penn Movies
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    All the Right Moves

    Tom Cruise, Lea Thompson

    Released1983

    Directed byMichael Chapman

    All the Right Moves is a 1983 drama film directed by Michael Chapman and starring Tom Cruise,... more on Wikipedia

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    #84 of 172 The Best Sports Movies Ever Made#142 of 151 The Most Inspirational Sports Movies

  • 8
    Rumble Fish is listed (or ranked) 8 on the list The Best Chris Penn Movies
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    Rumble Fish

    Nicolas Cage, Mickey Rourke

    Released1983

    Directed byFrancis Ford Coppola

    Rumble Fish is an American 1983 drama film directed by Francis Ford Coppola. It is based on... more on Wikipedia

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    #280 of 364 The Best Movies Based On Books#8 of 36 30+ Great Movies About Juvenile Delinquents

  • 9
    Rush Hour is listed (or ranked) 9 on the list The Best Chris Penn Movies
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    Rush Hour

    Jackie Chan, Roselyn Sánchez

    Released1998

    Directed byBrett Ratner

    Rush Hour is a 1998 American buddy action comedy film and the first installment in the Rush... more on Wikipedia

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    #34 of 50 The 50 Highest Grossing '90s Movies, Ranked#110 of 1,137 The Absolute Funniest Movies Of All Time

  • 10
    Short Cuts is listed (or ranked) 10 on the list The Best Chris Penn Movies
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    Short Cuts

    Robert Downey Jr., Julianne Moore

    Released1993

    Directed byRobert Altman

    Short Cuts is a 1993 American drama film directed by Robert Altman. Filmed from a screenplay... more on Wikipedia
  • 11
    Best of the Best is listed (or ranked) 11 on the list The Best Chris Penn Movies
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    Best of the Best

    James Earl Jones, Eric Roberts

    Released1989

    Directed byRobert Radler, Bob Radler

    Best of the Best is a 1989 American martial arts film directed by Bob Radler, and produced by... more on Wikipedia
  • 12
    The Boys Club is listed (or ranked) 12 on the list The Best Chris Penn Movies
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    The Boys Club

    Devon Sawa, Chris Penn

    Released1997

    Directed byJohn Fawcett

    The Boys Club is a 1997 crime thriller film directed by John Fawcett, written by Doug Smith... more on Wikipediaamazon_watch buy button
  • 13
    Stealing Harvard is listed (or ranked) 13 on the list The Best Chris Penn Movies
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    Stealing Harvard

    Leslie Mann, Megan Mullally

    Released2002

    Directed byBruce McCulloch

    This film is a 2002 comedy film directed by Canadian filmmaker Bruce McCulloch, about a man... more on Wikipedia
  • 14
    Kiss Kiss (Bang Bang) is listed (or ranked) 14 on the list The Best Chris Penn Movies
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    Kiss Kiss (Bang Bang)

    Paul Bettany, Stellan Skarsgård

    Released2001

    Directed byStewart Sugg

    Kiss Kiss (Bang Bang) is a 2001 English comedy film written and directed by Stewart Sugg. It... more on Wikipediaamazon_watch buy button
  • 15
    Mulholland Falls is listed (or ranked) 15 on the list The Best Chris Penn Movies
    5
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    Mulholland Falls

    Jennifer Connelly, Nick Nolte

    Released1996

    Directed byLee Tamahori

    Mulholland Falls is a 1996 American neo-noir thriller film directed by Lee Tamahori and... more on Wikipedia

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    #22 of 34 The Best Movies About Corrupt Cops#54 of 185 The Best Mystery Movies

  • 16
    The Wild Life is listed (or ranked) 16 on the list The Best Chris Penn Movies
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    The Wild Life

    Lea Thompson, Randy Quaid

    Released1984

    Directed byArt Linson

    The Wild Life is a 1984 comedy-drama film, written by Cameron Crowe and directed by Art... more on Wikipedia

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    #117 of 259 The Greatest Teen Movies of the 1980s#118 of 150 The Best R-Rated Buddy Movies

  • 17
    Murder by Numbers is listed (or ranked) 17 on the list The Best Chris Penn Movies
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    Murder by Numbers

    Sandra Bullock, Ryan Gosling

    Released2002

    Directed byBarbet Schroeder

    This film is a 2002 psychological thriller film produced and directed by Barbet Schroeder. It... more on Wikipediaamazon_watch buy button

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    #442 of 560 The Greatest Guilty Pleasure Movies#42 of 280 The Best Whodunit Movies

  • 18
    Made in USA is listed (or ranked) 18 on the list The Best Chris Penn Movies
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    Made in USA

    Chris Penn, Lori Singer

    Released1987

    Directed byKen Friedman

    Made in U.S.A. is a 1987 American crime drama / black comedy film directed by Ken Friedman... more on Wikipedia
  • 19
    The Pickle is listed (or ranked) 19 on the list The Best Chris Penn Movies
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    The Pickle

    Isabella Rossellini, Little Richard

    Released1993

    Directed byPaul Mazursky

    The Pickle is a 1993 film produced, written, and directed by Paul Mazursky, telling the story... more on Wikipedia
  • 20
    The Funeral is listed (or ranked) 20 on the list The Best Chris Penn Movies
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    The Funeral

    Christopher Walken, Isabella Rossellini

    Released1996

    Directed byAbel Ferrara

    The Funeral is a 1996 American crime-drama film directed by Abel Ferrara and starring... more on Wikipedia
  • 21
    Corky Romano is listed (or ranked) 21 on the list The Best Chris Penn Movies
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    Corky Romano

    Zach Galifianakis, Peter Falk

    Released2001

    Directed byRob Pritts

    Corky Romano is a 2001 American comedy film starring former Saturday Night Live cast member... more on Wikipedia
  • 22
    Masked and Anonymous is listed (or ranked) 22 on the list The Best Chris Penn Movies
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    Masked and Anonymous

    Penélope Cruz, Bob Dylan

    Released2003

    Directed byLarry Charles

    Masked and Anonymous is a 2003 comedy-drama film directed by Larry Charles. The film was... more on Wikipedia
  • 23
    Mobsters is listed (or ranked) 23 on the list The Best Chris Penn Movies
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    Mobsters

    Patrick Dempsey, Christian Slater

    Released1991

    Directed byMichael Karbelnikoff

    This film is a 1991 drama film detailing the creation of The Commission. Set in New York City,... more on Wikipediaamazon_watch buy button
  • 24
    The Music of Chance is listed (or ranked) 24 on the list The Best Chris Penn Movies
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    The Music of Chance

    James Spader, Mandy Patinkin

    Released1993

    Directed byPhilip Haas

    The Music of Chance is a 1993 American drama film directed by Philip Haas. It was screened in... more on Wikipedia
  • 25
    One Tough Cop is listed (or ranked) 25 on the list The Best Chris Penn Movies
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    One Tough Cop

    Gina Gershon, Stephen Baldwin

    Released1998

    Directed byBruno Barreto

    One Tough Cop is a 1998 American action crime film. It was directed by Bruno Barreto and... more on Wikipediaamazon_watch buy button
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