Entertainment The Best Sean Penn Movies  

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2.2k votes 481 voters 38.5k 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.

list ordered by
1
116 25
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Emmy Rossum, Sean Penn, Kevin Bacon
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
2
105 28
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Sean Penn, Susan Sarandon, Jack Black
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
3
111 40
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Nicolas Cage, Sean Penn, Jennifer Jason Leigh
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
4
88 27
Carlito's Way is listed (or ranked) 4 on the list The Best Sean Penn Movies
Al Pacino, Sean Penn, Viggo Mortensen
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
5
68 18
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Sean Penn, Michael Douglas, Spike Jonze
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
6
91 36
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Michelle Pfeiffer, Sean Penn, Dakota Fanning
I Am Sam is a 2001 American drama film written and directed by Jessie Nelson, and starring Sean Penn as a father with a developmental disability, Dakota Fanning as his inquisitive seven-year-old ...more
7
77 29
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James Franco, Sean Penn, Josh Brolin
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
8
75 35
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Sean Penn, Ally Sheedy, Clancy Brown
Bad Boys is a 1983 drama film written by Richard Di Lello and directed by Rick Rosenthal.
9
55 22
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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
10
51 20
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Naomi Watts, Sean Penn, Benicio del Toro
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
11
53 23
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Sean Penn, Robert Duvall, Don Cheadle
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
12
35 13
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Elizabeth Hurley, Sean Penn, Josh Lucas
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
13
32 11
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Tom Cruise, Sean Penn, George C. Scott
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
14
50 26
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George Clooney, John Travolta, Sean Penn
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
15
36 17
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Sean Penn, Timothy Hutton, Michael Ironside
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
16
28 11
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Uma Thurman, Sean Penn, 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
17
32 15
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Sean Penn, Gary Oldman, Robin Wright
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
18
34 18
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Nicole Kidman, Sean Penn, Catherine Keener
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.
19
25 12
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Meg Ryan, Anna Paquin, Sean Penn
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 title refers to dialogue in Act I, ...more
20
29 17
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Sean Penn, Michael J. Fox, John C. Reilly
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
21
24 13
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Sean Penn, Frances McDormand, David Byrne
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
22
20 10
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Nicolas Cage, Sean Penn, Crispin Glover
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
23
20 11
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Sean Penn, Anne Bancroft, Kristin Scott Thomas
Up at the Villa is a 2000 drama film written by W. Somerset Maugham and directed by Philip Haas.
24
20 12
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Naomi Watts, Sean Penn, Don Cheadle
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
14 7
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Johnny Depp, Sean Penn, Javier Bardem
Before Night Falls is a 2000 American drama film directed by Julian Schnabel. The screenplay is based on the autobiography of the same name of Reinaldo Arenas, which was published in English in ...more