Entertainment
73 voters

The Best Chris Penn Movies

Updated September 23, 2019 635 votes 73 voters 7.5k 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?"

list.itemsDescription

...more
  • 1
    37
    8

    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 stars in the lead role. This movie bears a striking similarity to the classic Western Shane, as well as...  more

    More Pale Rider 

    #205 of 675 The Best Movies Roger Ebert Gave Four Stars#11 of 401 The Best Western Movies Ever Made

  • 2
    31
    6

    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. The film stars Christian Slater and Patricia Arquette with a supporting cast featuring Dennis Hopper, Val...  more

    More True Romance 

    #185 of 440 The Best Movies Of The 1990s#26 of 123 The Best Mafia Films Of All Time

  • 3
    30
    10

    Released1995

    Directed byBeeban Kidron

    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 trip....  more

    More To Wong Foo, Thanks for Everything! Julie Newmar 

    #162 of 252 The Funniest '90s Movies#702 of 783 The Greatest Chick Flicks Ever Made

  • 4
    24
    5

    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, Craig T. Nelson, Lea Thompson, Chris Penn, and Gary Graham. It was filmed on location during WPIAL...  more

    More All the Right Moves 

    #79 of 205 The Best Sports Movies Ever Made#8 of 66 The Best High School Sports Movies

  • 5
    18
    3

    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 the novel Rumble Fish by S. E. Hinton, who also co-wrote the screenplay. The film centers on the...  more

    More Rumble Fish 

    #356 of 386 The Best Movies Based On Books#7 of 36 30+ Great Movies About Juvenile Delinquents

  • 6
    19
    6

    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 McCormack, an upbeat Chicago teen who moves to a small town in which, as a result of the efforts of a...  more

    More Footloose 

    #2100 of 2,809 The Greatest Albums of All-Time#88 of 126 The Greatest Date Movies Of All Time

  • 7
    19
    6

    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 by Altman and Frank Barhydt, it is inspired by nine short stories and a poem by Raymond Carver....  more

    More Short Cuts 

    #84 of 90 The Best Movies That Are Super Long#20 of 20 Robert Downey Jr. Roles (Besides Iron Man) That Prove He's A Great Actor

  • 8
    15
    3

    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 and Peter Wellington, and starring Chris Penn, Devon Sawa, Dominic Zamprogna, and Stuart Stone. It was...  more
  • 9
    13
    4

    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 rural Pennsylvania crime family led by Bruce Johnston, Sr. which operated during the 1960s and 1970s. It...  more
  • 10
    23
    15

    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 a botched diamond heist. The film was the debut of director and writer Quentin Tarantino, and stars...  more

    More Reservoir Dogs 

    #129 of 375 'Old' Movies Every Young Person Needs To Watch In Their Lifetime#930 of 1,141 The Absolute Funniest Movies Of All Time

  • 11
    12
    4

    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 from a screenplay by Zbigniew Kempinski. The film stars Adrian Pasdar and Chris Penn as two young men who...  more
  • 12
    12
    5

    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 written by Larry Charles and Bob Dylan, the latter under the pseudonym "Sergei Petrov". It stars Dylan...  more

    More Masked and Anonymous 

    #24 of 71 The Best Val Kilmer Movies#70 of 73 The Best Jeff Bridges Movies

  • 13
    10
    4

    Aftermath

    Anthony Michael Hall, Tony Danza

    Released2013

    Directed byThomas Farone

    Aftermath is a 2013 crime thriller film written and directed by Thomas Farone....  more
  • 14
    10
    5

    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 written by Pete Dexter. It stars Nick Nolte, Jennifer Connelly, Chazz Palminteri, Michael Madsen, Chris Penn,...  more
  • 15
    10
    5

    Deceiver

    Renée Zellweger, Tim Roth

    Released1997

    Directed byJosh Pate, Jonas Pate

    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....  more
  • 16
    12
    8

    Starsky & Hutch

    Snoop Dogg, Carmen Electra

    Released2004

    Directed byTodd Phillips

    Starsky & Hutch is a 2004 American action comedy film directed by Todd Phillips. The film stars Ben Stiller as David Starsky and Owen Wilson as Ken "Hutch" Hutchinson and is a film adaptation of the...  more

    More Starsky & Hutch 

    #610 of 924 The All-Time Greatest Comedy Films#73 of 117 The Best Movies Based on TV Shows

  • 17
    12
    9

    Beethoven's 2nd

    Bonnie Hunt, Charles Grodin

    Released1993

    Directed byRod Daniel

    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

    More Beethoven's 2nd 

    #28 of 40 The Funniest Movies About Animals#54 of 77 The Best Live Action Animal Movies for Kids

  • 18
    8
    3

    Holly

    Virginie Ledoyen, Chris Penn

    Released2007

    Directed byGuy Moshe

    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 Livingston,...  more
  • 19
    0
    3

    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 of a formerly powerful film director whose recent string of flops has forced him to make a commercial...  more
  • 20
    8
    5

    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 Christopher Walken, Chris Penn, Annabella Sciorra, Isabella Rossellini, Vincent Gallo, Benicio del Toro and...  more
  • 21
    8
    4

    The Darwin Awards

    Winona Ryder, Julianna Margulies

    Released2006

    Directed byFinn Taylor

    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
  • 22
    8
    4

    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 Phillip Rhee, who also co-stars in the film. The film also starring Eric Roberts, James Earl Jones and...  more
  • 23
    7
    4

    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 features Stellan Skarsgård, Chris Penn, and Paul Bettany....  more
  • 24
    0
    3

    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 the Un Certain Regard section at the 1993 Cannes Film Festival. It is based on the book of the same name....  more
  • 25
    0
    3

    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 written by Jeremy Iacone. The movie stars Stephen Baldwin as the protagonist and first-person narrator Bo...  more