Entertainment The Best Chris Penn Movies  

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386 votes 60 voters 7k 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
18 5
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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
19 6
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
19 7
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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
10 3
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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
5
9 3
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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
6
11 5
True Romance is listed (or ranked) 6 on the list The Best Chris Penn Movies
Brad Pitt, Val Kilmer, Samuel L. Jackson
True Romance is a 1993 American film directed by Tony Scott and written by Quentin Tarantino. The film stars Christian Slater and Patricia Arquette with a supporting cast featuring Dennis ...more
7
11 5
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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
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
8 5
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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
10
5 2
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Jennifer Connelly, Nick Nolte, John Malkovich
Mulholland Falls is a 1996 American neo-noir thriller film directed by Lee Tamahori and written by Pete Dexter. It stars Nick Nolte, Jennifer Connelly, Chazz Palminteri, Michael Madsen, Chris ...more
11
7 5
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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
12
8 7
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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
13
4 3
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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
14
6 6
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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
15
6 6
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Patrick Dempsey, Christian Slater, Michael Gambon
This film is a 1991 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
16
5 5
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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
4 4
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Sandra Bullock, Ryan Gosling, Nick Offerman
This film 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 Leopold ...more
18
6 7
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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
19
4 5
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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
20
4 5
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Leslie Mann, Megan Mullally, Tom Green
This film is a 2002 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 Tom Green. ...more
21
2 3
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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
22
2 3
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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
23
5 7
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Zach Galifianakis, Peter Falk, Chris Kattan
Corky Romano is a 2001 American 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 was ...more
24
2 4
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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
2 4
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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