Film The Best Chris Penn Movies  

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361 votes 53 voters 6.8k views 41 items

List Rules Vote 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?"

Brett Ratner and Quentin Tarantino are among those who directed Chris Penn at one point or another during their careers in the film industry.

list ordered by

1
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Clint Eastwood, Chris Penn, Michael Moriarty Pale Rider is a 1985 American western film produced and directed by Clint Eastwood, who also stars in the lead role. This movie bears a striking similarity to the classic Western Shane, as well ...more

2
17 4
Reservoir Dogs is listed (or ranked) 2 on the list The Best Chris Penn Movies
Quentin Tarantino, Steve Buscemi, Tim Roth Reservoir Dogs is a 1992 American ensemble crime film that depicts the events before and after a botched diamond heist. The film was the debut of director and writer Quentin Tarantino, and stars ...more

3
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Sarah Jessica Parker, Kevin Bacon, John Lithgow Footloose is a 1984 American musical-drama directed by Herbert Ross. It tells the story of Ren McCormack, an upbeat Chicago teen who moves to a small town in which, as a result of the efforts of ...more

4
11 4
True Romance is listed (or ranked) 4 on the list The Best Chris Penn Movies
Brad Pitt, Val Kilmer, Samuel L. Jackson True Romance is a 1993 American romantic crime film directed by Tony Scott and written by Quentin Tarantino. The film stars Christian Slater and Patricia Arquette with a supporting cast ...more

5
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Sean Penn, Christopher Walken, Kiefer Sutherland At Close Range is a 1986 crime drama film directed by James Foley, based on the real life rural Pennsylvania crime family led by Bruce Johnston, Sr. which operated during the 1960s and 1970s. It ...more

6
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Tom Cruise, Lea Thompson, Craig T. Nelson All the Right Moves is a 1983 drama film directed by Michael Chapman and starring Tom Cruise, Craig T. Nelson, Lea Thompson, Chris Penn, and Gary Graham. It was filmed on location during WPIAL ...more

7
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Nicolas Cage, Mickey Rourke, Diane Lane Rumble Fish is an American 1983 drama film directed by Francis Ford Coppola. It is based on the novel Rumble Fish by S. E. Hinton, who also co-wrote the screenplay. The film centers on the ...more

8
8 5
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Robert Downey Jr., Julianne Moore, Tim Robbins Short Cuts is a 1993 American drama film directed by Robert Altman. Filmed from a screenplay by Altman and Frank Barhydt, it is inspired by nine short stories and a poem by Raymond Carver. ...more

9
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Jennifer Connelly, Nick Nolte, John Malkovich Mulholland Falls is a 1996 American neo-noir crime thriller film directed by Lee Tamahori and written by Pete Dexter. It stars Nick Nolte, Jennifer Connelly, Chazz Palminteri, Michael Madsen, ...more

10
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Jackie Chan, Roselyn Sánchez, Chris Tucker Rush Hour is a 1998 American buddy action comedy film and the first installment in the Rush Hour series, directed by Brett Ratner and starring Jackie Chan and Chris Tucker. It was followed by ...more

11
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Patrick Dempsey, Christian Slater, Michael Gambon Mobsters is a 1991 crime-drama film detailing the creation of The Commission. Set in New York City, taking place from 1917 to 1931, it is a semi-fictitious account of the rise of Charles ...more

12
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James Earl Jones, Eric Roberts, Louise Fletcher Best of the Best is a 1989 American martial arts film directed by Bob Radler, and produced by Phillip Rhee, who also co-stars in the film. The film also starring Eric Roberts, James Earl Jones ...more

13
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Robin Williams, Naomi Campbell, Patrick Swayze To Wong Foo, Thanks for Everything! Julie Newmar is a 1995 American comedy film, starring Wesley Snipes, Patrick Swayze, and John Leguizamo as three New York drag queens who embark on a road ...more

14
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Bonnie Hunt, Charles Grodin, Chris Penn Beethoven's 2nd is a 1993 family film directed by Rod Daniel, and the first sequel to the 1992 film, Beethoven. It starred Charles Grodin, Bonnie Hunt, and Debi Mazar. It is the second of eight ...more

15
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Penélope Cruz, Bob Dylan, Mickey Rourke Masked and Anonymous is a 2003 comedy-drama film directed by Larry Charles. The film was written by Larry Charles and Bob Dylan, the latter under the pseudonym "Sergei Petrov". It ...more

16
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Lea Thompson, Randy Quaid, Rick Moranis The Wild Life is a 1984 comedy-drama film, written by Cameron Crowe and directed by Art Linson. The film is only available on VHS and Laserdisc in pan and scan with stereo analog tracks. No DVD ...more

17
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Christopher Walken, Isabella Rossellini, Benicio del Toro The Funeral is a 1996 American crime-drama film directed by Abel Ferrara and starring Christopher Walken, Chris Penn, Annabella Sciorra, Isabella Rossellini, Vincent Gallo, Benicio del Toro and ...more

18
3 4
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Sandra Bullock, Ryan Gosling, Nick Offerman Murder by Numbers is a 2002 psychological thriller film produced and directed by Barbet Schroeder. It stars Sandra Bullock, Ben Chaplin, Ryan Gosling and Michael Pitt. It is loosely based on the ...more

19
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Tom Sizemore, Jim Belushi, Mary Stuart Masterson The Florentine is a 1999 film directed Nick Stagliano and produced by Francis Ford Coppola's American Zoetrope. It stars Jeremy Davies, Virginia Madsen, Luke Perry, Mary Stuart Masterson, ...more

20
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Snoop Dogg, Carmen Electra, Will Ferrell Starsky & Hutch is a 2004 American crime action comedy film directed by Todd Phillips. The film stars Ben Stiller as David Starsky and Owen Wilson as Ken "Hutch" Hutchinson and is ...more

21
5 7
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Zach Galifianakis, Peter Falk, Chris Kattan Corky Romano is a 2001 American mafia comedy film starring former Saturday Night Live cast member Chris Kattan. Also starring are Fred Ward, Vinessa Shaw, Chris Penn, and Peter Berg. The movie ...more

22
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Leslie Mann, Megan Mullally, Tom Green Stealing Harvard is a 2002 crime comedy film directed by Canadian filmmaker Bruce McCulloch, about a man who resorts to crime to pay for his niece's Harvard tuition. The film stars Jason Lee and ...more

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Winona Ryder, Julianna Margulies, Juliette Lewis The Darwin Awards is a 2006 American adventure comedy film based on the website of the same name. Written and directed by Finn Taylor, the film premiered January 25, 2006, at the Sundance Film ...more

24
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Paul Bettany, Stellan Skarsgård, Chris Penn Kiss Kiss (Bang Bang) is a 2001 English comedy film written and directed by Stewart Sugg. It features Stellan Skarsgård, Chris Penn, and Paul Bettany.

25
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Chris Penn, Lori Singer, Adrian Pasdar Made in U.S.A. is a 1987 American crime drama / black comedy film directed by Ken Friedman from a screenplay by Zbigniew Kempinski. The film stars Adrian Pasdar and Chris Penn as two young men ...more

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Elisabeth Moss, Harvey Keitel, Kelly Lynch Imaginary Crimes is a 1994 drama film directed by Anthony Drazan, and an adaptation of Sheila Ballantyne's 1982 novel of the same name. The film stars Harvey Keitel and Fairuza Balk, and tells ...more

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Sherilyn Fenn, Jeffrey Wright, Chris Penn Cement is a 2000 crime drama-thriller film directed by Adrian Pasdar and written by Justin Monjo. The film was shot in Los Angeles, California, USA, and was Pasdar's first film as director.

28
1 3
Fist of the North Star is listed (or ranked) 28 on the list The Best Chris Penn Movies
Malcolm McDowell, Chris Penn, Gary Daniels An American-produced live-action movie version of Fist of the North Star was released in 1995, directed by Tony Randel based on a script by Peter Atkins and Wynne McLaughlin. The movie, loosely ...more

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Devon Sawa, Chris Penn, Amii Stewart The Boys Club is a 1997 crime thriller film directed by John Fawcett, written by Doug Smith and Peter Wellington, and starring Chris Penn, Devon Sawa, Dominic Zamprogna, and Stuart Stone. It was ...more

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Anthony Michael Hall, Tony Danza, Chris Penn Aftermath is a 2013 crime thriller film written and directed by Thomas Farone.

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Shelter Island Ally Sheedy, Stephen Baldwin, Patsy Kensit Shelter Island is a 2003 thriller film directed by Geoffrey Schaaf.

32
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Renée Zellweger, Tim Roth, Ellen Burstyn Deceiver is a 1997 murder mystery film. It won Best Cinematography and Best Screenplay at the 1997 Stockholm Film Festival, and the Special Jury Prize at the 1998 Cognac Police Film Festival.

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Redemption Carrie Stevens, Chris Penn, Cynthia Rothrock Redemption is a 2002 action film written by Jack Capece and directed by Art Camacho.

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Celebrating AFI Mel Gibson, James Franco, Martin Sheen Celebrating AFI is a 1998 short film directed and written by Brian Hecker.

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Papertrail Chris Penn, Kari Matchett, Jennifer Dale Papertrail is a 1997 film directed by Damian Lee.

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Chris Penn, Don "The Dragon" Wilson, Meg Foster Future Kick is a 1991 film directed by Damian Klaus.

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James Spader, Mandy Patinkin, Charles Durning The Music of Chance is a 1993 American drama film directed by Philip Haas. It was screened in the Un Certain Regard section at the 1993 Cannes Film Festival. It is based on the book of the same

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Isabella Rossellini, Little Richard, Dudley Moore The Pickle is a 1993 film produced, written, and directed by Paul Mazursky, telling the story of a formerly powerful film director whose recent string of flops has forced him to make a ...more

39
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Virginie Ledoyen, Chris Penn, Ron Livingston Holly is a 2006 drama film about an American stolen artifacts dealer in Cambodia who tries to save a young girl from child traffickers. The film was directed by Guy Moshe, and stars Ron ...more

40
0 3
One Tough Cop is listed (or ranked) 40 on the list The Best Chris Penn Movies
Gina Gershon, Stephen Baldwin, Chris Penn One Tough Cop is a 1998 American action crime film. It was directed by Bruno Barreto and written by Jeremy Iacone. The movie stars Stephen Baldwin as the protagonist and first-person narrator Bo ...more

41
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David Boreanaz, Eric Roberts, Chris Penn Best of the Best 2 is a 1993 martial arts film directed by Robert Radler, and starring Eric Roberts and Phillip Rhee. It is the first sequel to the 1989 film Best of the Best. The plot follows ...more