Film The Best Sean Penn Movies  

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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

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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

100 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

107 37
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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

84 26
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

64 17
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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

87 33
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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

75 27
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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

70 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.

51 21
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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

47 19
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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

48 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

33 12
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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

30 10
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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

27 9
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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

47 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

33 16
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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

32 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.

28 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

20 9
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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.

22 11
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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

22 12
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Kate Winslet, Sean Penn, Jude Law All the King's Men is a 2006 film adaptation of the 1946 Pulitzer Prize-winning novel All the King's Men by Robert Penn Warren. It was directed by Steven Zaillian, who also produced and ...more

23 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

26 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

17 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

19 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

13 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

21 15
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Demi Moore, Robert De Niro, Sean Penn 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

14 9
Gangster Squad is listed (or ranked) 28 on the list The Best Sean Penn Movies
Emma Stone, Sean Penn, Ryan Gosling This film is a 2013 American film directed by Ruben Fleischer, from a screenplay written by Will Beall and starring Josh Brolin, Ryan Gosling, Nick Nolte, Emma Stone, and Sean Penn. The story is ...more

16 12
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Jennifer Lopez, Sean Penn, Claire Danes U Turn is a 1997 romantic comedy thriller film directed by Oliver Stone, based on the book Stray Dogs by John Ridley. It stars Sean Penn, Billy Bob Thornton, Jennifer Lopez, Jon Voight, Powers ...more

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Sean Penn, Martin Sheen, Sam Wanamaker Judgment in Berlin is a 1988 drama film written by Herbert J. Stern, Joshua Sinclair and Leo Penn, and directed by Leo Penn.

20 17
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Brad Pitt, Sean Penn, Jessica Chastain The Tree of Life is a 2011 American experimental drama film written and directed by Terrence Malick and starring Brad Pitt, Sean Penn, and Jessica Chastain. The film chronicles the origins and ...more

15 14
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Naomi Watts, Sean Penn, Ty Burrell Fair Game is a 2010 biographical spy drama film directed by Doug Liman and starring Naomi Watts and Sean Penn. It is based on Valerie Plame's memoir, Fair Game: My Life as a Spy, My Betrayal by ...more

10 9
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Sean Penn, Catherine Deneuve, Iggy Pop Persepolis is a 2007 French-Iranian-American animated film based on Marjane Satrapi's autobiographical graphic novel of the same name. The film was written and directed by Satrapi with Vincent ...more

9 8
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Sean Penn, Claire Danes, Joaquin Phoenix It's All About Love is a 2003 romance-drama film written and directed by Thomas Vinterberg. Its narrative can be classified as apocalyptic science fiction, but Vinterberg prefers to call it ...more

7 6
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Sean Penn, Donald Sutherland, Christine Baranski Crackers is a 1984 American film directed by Louis Malle. It was entered into the 34th Berlin International Film Festival. Written by Jeffrey Fiskin, the film is about a group of small-time ...more

5 4
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Robert De Niro, Robin Williams, Sean Penn Dear America: Letters Home from Vietnam is an American grammy Award–winning 1987 documentary, inspired by the anthology of the same title, directed by Bill Couturié. Using real letters ...more

5 4
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Jodie Foster, Steven Spielberg, Rob Cohen The Cutting Edge: The Magic of Movie Editing is a 2004 documentary film directed by filmmaker Wendy Apple. The film is about the art of film editing. Clips are shown from many groundbreaking ...more

10 10
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Kristen Stewart, Bruce Willis, Robert De Niro What Just Happened is a satirical comedy-drama directed by Barry Levinson and starring Robert De Niro. The supporting cast includes Catherine Keener, Robin Wright Penn, Stanley Tucci, and Sean ...more

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John Travolta, Sean Penn, Robin Wright She's So Lovely is a 1997 film directed by Nick Cassavetes, written by John Cassavetes. At the time of its release, it received special attention because, eight years after his death, it was the ...more

4 4
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Phil Ochs: There but for Fortune Sean Penn, Joan Baez, Christopher Hitchens Phil Ochs: There but for Fortune is a documentary film on the life and times of folk singer-songwriter Phil Ochs. The film, released theatrically in January 2011, was written and directed by ...more

5 6
Heart Stopper is listed (or ranked) 41 on the list The Best Sean Penn Movies
Heart Stopper Morgan Freeman, Sean Penn, Heather Graham Heart Stopper is a 2012 thriller film written by Michael Z. Gordon and directed by Paul Flaherty.

3 4
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Ben Affleck, Matt Damon, Marisa Tomei The People Speak is a documentary tv program/film.

4 6
This So-Called Disaster is listed (or ranked) 43 on the list The Best Sean Penn Movies
This So-Called Disaster Sean Penn, Nick Nolte, T Bone Burnett This So-Called Disaster is a 2003 documentary film directed by Michael Almereyda.

3 5
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A Constant Forge Peter Falk A Constant Forge is a 2000 documentary film directed by Charles Kiselyak about the life and work of John Cassavetes. It contains interviews with Cassavetes himself as well as recollections by ...more

3 5
Buy the Ticket, Take the Ride is listed (or ranked) 45 on the list The Best Sean Penn Movies
Buy the Ticket, Take the Ride Bill Murray, Nick Nolte, Gary Busey Buy the Ticket, Take the Ride is a 2006 documentary film written by Tom Marksbury and directed by Tom Thurman.

6 9
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Love Sean Penn, Robin Wright, William Hurt Loved is a 1997 film directed by Erin Dignam and starring Robin Wright Penn and William Hurt

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Madonna, Sean Penn, George Harrison Shanghai Surprise is a 1986 British adventure comedy film starring then-newlyweds Sean Penn and Madonna, produced by George Harrison's HandMade Films and distributed by Metro-Goldwyn-Mayer. ...more

2 5
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Robert Downey Jr., Alyssa Milano, Sean Penn Hugo Pool is a 1997 American romantic comedy film, directed by Robert Downey, Sr., starring Alyssa Milano and Patrick Dempsey.

2 5
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War Made Easy: How Presidents & Pundits Keep Spinning Us to Death Sean Penn Narrated by Sean Penn and based on the work of media critic and best- selling author Norman Solomon, who traveled with Penn to Baghdad just before the war to call attention to the dangers of a ...more