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The Best Sean Penn Movies 

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Updated November 13, 2019 2.4k votes 516 voters 39.7k views 55 items

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

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

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

List films include Up at the Villa, This So-Called Disaster and many more.

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

Notable directors that have worked with Sean Penn include names like Brian De Palma, Terrence Malick and Woody Allen. Movie fans who love Sean Penn have also been known to enjoy films starring Andrew Dice Clay and Josh Brolin.

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1
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Emmy Rossum, Sean Penn, Kevin Bacon

Released: 2003

Directed by: Clint Eastwood

Mystic River is a 2003 American mystery drama film directed and scored by Clint Eastwood. It stars Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Marcia Gay Harden, and Laura Linney. ...more

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#20 of 253 The Best Psychological Thrillers of All Time #328 of 548 The Greatest Movies for Guyslisted on Every Oscar Winning Film Ever

2
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Nicolas Cage, Sean Penn, Jennifer Jason Leigh

Released: 1982

Directed by: Amy Heckerling

Fast Times at Ridgemont High is a 1982 American coming-of-age teen comedy film written by Cameron Crowe, adapted from his 1981 book of the same name. As a freelance writer for Rolling Stone ...more

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#90 of 349 'Old' Movies Every Young Person Needs To Watch In Their Lifetime #69 of 1,025 The All-Time Greatest Comedy Films #143 of 548 The Greatest Movies for Guys

3
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Sean Penn, Susan Sarandon, Jack Black

Released: 1995

Directed by: Tim Robbins

This film is a 1995 American drama film starring Susan Sarandon and Sean Penn, and co-produced and directed by Tim Robbins, who adapted the screenplay from the non-fiction book of the same name. ...more

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#47 of 157 The Best Movies You Never Want to Watch Again #213 of 710 The Best Movies Roger Ebert Gave Four Starslisted on Every Oscar Winning Film Ever

4
Carlito's Way is listed (or ranked) 4 on the list The Best Sean Penn Movies
Al Pacino, Sean Penn, Viggo Mortensen

Released: 1993

Directed by: Brian De Palma

Carlito's Way is a 1993 American drama film directed by Brian De Palma, based on the novels Carlito's Way and After Hours by Judge Edwin Torres. The film adaptation was scripted by David Koepp. ...more

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#10 of 114 The Best Mafia Films #26 of 529 The Greatest Crime Movies Ever Made #53 of 66 The Best Thriller Movies of the 1990s

5
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Sean Penn, Dakota Fanning, Michelle Pfeiffer

Released: 2001

Directed by: Jessie Nelson

I Am Sam is a 2001 American drama film directed by Jessie Nelson. A mentally handicapped man (Sean Penn) fights for custody of his 7-year-old daughter (Dakota Fanning) and in the process teaches ...more

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#53 of 293 The Top Tearjerker Movies That Make Men Cry #128 of 301 The Greatest Soundtracks of All Time #39 of 70 The Most Pretentious Movies Ever Made

6
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Sean Penn, Michael Douglas, Spike Jonze

Released: 1997

Directed by: David Fincher, Pedro Coutinho

The Game is a 1997 American mystery thriller film directed by David Fincher, starring Michael Douglas and Sean Penn, and produced by Propaganda Films and PolyGram Filmed Entertainment. It tells ...more

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#21 of 253 The Best Psychological Thrillers of All Time #15 of 24 The Best Movies with Twist Endings #27 of 149 The Best and Scariest Psychological Thrillers of All Time

7
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Sean Penn, Ally Sheedy, Clancy Brown

Released: 1983

Directed by: Rick Rosenthal

Bad Boys is a 1983 drama film written by Richard Di Lello and directed by Rick Rosenthal.

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#17 of 26 The Best Brat Pack Movies #31 of 314 The Greatest Teen Movies of the 1980s #22 of 136 The Best Prison Movies

8
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James Franco, Sean Penn, Josh Brolin

Released: 2008

Directed by: Gus Van Sant

Milk is a 2008 American biographical film based on the life of gay rights activist and politician Harvey Milk, who was the first openly gay person to be elected to public office in California, ...more

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#93 of 234 The Best Movies Based On True Stories #122 of 140 The Most Awkward Movies to Watch with Your Parentslisted on Every Oscar Winning Film Ever

9
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Sean Penn, Christopher Walken, Kiefer Sutherland

Released: 1986

Directed by: James 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

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#494 of 571 The Greatest Movies Of The 1980s, Ranked #22 of 101 The Best Christopher Walken Movies #37 of 70 The Best Kiefer Sutherland Movies

10
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Naomi Watts, Sean Penn, Benicio del Toro

Released: 2003

Directed by: Alejandro González Iñárritu

21 Grams is a 2003 American drama film directed by Mexican director Alejandro González Iñárritu from a screenplay written by Guillermo Arriaga. It stars Sean Penn, Naomi ...more

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#109 of 212 The Best Drug Movies of All Time #24 of 32 30+ Great Movies About Depression in Women #56 of 125 The Best Movies About Tragedies

11
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Sean Penn, Robert Duvall, Don Cheadle

Released: 1988

Directed by: Dennis Hopper

Colors is a 1988 American police procedural action film starring Sean Penn and Robert Duvall, and directed by Dennis Hopper. The film takes place in the gang ridden neighborhoods of South ...more

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#523 of 728 The Best Black Movies Ever Made, Ranked #11 of 16 The Most Powerful Movies About Police Brutality #58 of 144 The Best Films Directed by Famous Actors

12
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George Clooney, John Travolta, Sean Penn

Released: 1998

Directed by: Terrence Malick

The Thin Red Line is a 1998 American ensemble epic film written and directed by Terrence Malick. Based on the novel by James Jones, it tells a fictionalized version of the Battle of Mount ...more

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#37 of 375 The 50+ Best War Movies Ever Made, Ranked #49 of 222 The Greatest World War II Movies of All Time #157 of 581 The Greatest Film Scores of All Time

13
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Sean Penn, Timothy Hutton, Michael Ironside

Released: 1985

Directed by: John Schlesinger

The Falcon and the Snowman is a 1985 spy film directed by John Schlesinger about two young American men, Christopher Boyce and Daulton Lee, who sold U.S. security secrets to the Soviet Union. ...more

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#62 of 75 The Greatest Movies About CIA Agents & Operatives #64 of 323 The Best Political Films Ever Made #250 of 305 The Best Military Movies Ever Made

14
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Elizabeth Hurley, Sean Penn, Josh Lucas

Released: 2000

Directed by: Kathryn Bigelow

The Weight of Water is a 2000 French-American mystery thriller film based on Anita Shreve's 1997 novel of the same name. Directed by Kathryn Bigelow, the film stars Elizabeth Hurley, Catherine ...more
15
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Tom Cruise, Sean Penn, George C. Scott

Released: 1981

Directed by: Harold Becker

Taps is a 1981 drama film starring George C. Scott and Timothy Hutton, with Ronny Cox, Tom Cruise, Sean Penn, and Evan Handler in supporting roles. Hutton was nominated for a Golden Globe award ...more

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#297 of 571 The Greatest Movies Of The 1980s, Ranked #34 of 42 The All-Time Best Tom Cruise Movies #80 of 154 The Most Utterly Depressing Movies Ever Made

16
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Sean Penn, Gary Oldman, Robin Wright

Released: 1990

Directed by: Phil Joanou

State of Grace is a 1990 neo-noir film starring Sean Penn, Ed Harris and Gary Oldman, also featuring Robin Wright, John Turturro and John C. Reilly. Written by Dennis McIntyre and directed by ...more

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#52 of 114 The Best Mafia Films #348 of 529 The Greatest Crime Movies Ever Made #98 of 145 The Best Police Movies

17
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Nicole Kidman, Sean Penn, Catherine Keener

Released: 2005

Directed by: Sydney Pollack

The Interpreter is a 2005 political thriller film starring Nicole Kidman, Sean Penn, and Catherine Keener. It was the final film to be directed by Sydney Pollack.

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#25 of 136 The Best Political Thriller Movies #9 of 70 The Best Nicole Kidman Movies #61 of 73 The Best Assassination Movies

18
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Uma Thurman, Sean Penn, Woody Allen

Released: 1999

Directed by: Woody Allen

Sweet and Lowdown is a 1999 American comedy-drama film written and directed by Woody Allen. The film tells the story, set in the 1930s, of a fictional jazz guitarist named Emmet Ray who regards ...more
19
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Sean Penn, Michael J. Fox, John C. Reilly

Released: 1989

Directed by: Brian De Palma

This film is a 1989 drama film directed by Brian De Palma, with a screenplay by David Rabe, based on the actual events of the incident on Hill 192 in 1966 during Vietnam. It stars Michael J. Fox ...more

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#182 of 375 The 50+ Best War Movies Ever Made, Ranked #498 of 571 The Greatest Movies Of The 1980s, Ranked #179 of 305 The Best Military Movies Ever Made

20
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Nicolas Cage, Sean Penn, Crispin Glover

Released: 1984

Directed by: Richard Benjamin

Racing with the Moon is a 1984 American drama film starring Sean Penn, Elizabeth McGovern, and Nicolas Cage. It was directed by Richard Benjamin and written by Steven Kloves. The original music ...more

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#355 of 439 The Funniest '80s Movies #79 of 103 The Best Nicolas Cage Movies #38 of 45 The Best Mainstream Movies That Flash a Lil Male Nudity

21
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Meg Ryan, Anna Paquin, Sean Penn

Released: 1998

Directed by: Anthony Drazan

Hurlyburly is a 1998 independent film, based on the acclaimed 1984 play of the same name by David Rabe, who adapted it into a screenplay for the film. The film was directed by Anthony Drazan. ...more
22
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Sean Penn, Frances McDormand, David Byrne

Released: 2011

Directed by: Paolo Sorrentino

This Must Be the Place is a 2011 European drama film directed by Paolo Sorrentino, written by Sorrentino and Umberto Contarello and released in the U.S. in late 2012. It stars Sean Penn and ...more
23
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Demi Moore, Robert De Niro, Sean Penn

Released: 1989

Directed by: Neil Jordan

We're No Angels is a 1989 comedy film directed by Neil Jordan. It stars Robert De Niro, Sean Penn, and Demi Moore. This was Jordan's last film to receive a PG-13 rating by the MPAA, until Ondine ...more

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#218 of 439 The Funniest '80s Movies #24 of 26 The Best Brat Pack Movies #102 of 136 The Best Prison Movies

24
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Naomi Watts, Sean Penn, Don Cheadle

Released: 2004

Directed by: Niels Mueller

This film is a 2004 American film, directed by Niels Mueller. It stars Sean Penn, Don Cheadle and Naomi Watts, and is based on the story of Samuel Byck, who plotted against Richard Nixon in ...more
25
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Sean Penn, Anne Bancroft, Kristin Scott Thomas

Released: 2000

Directed by: Philip Haas

Up at the Villa is a 2000 drama film written by W. Somerset Maugham and directed by Philip Haas.