Rank of Sean Penn's movies by Box Office performance.
by CZJFan87 | created - 14 Mar 2016 | updated - 13 Dec 2016 | PublicWorldwide performance. Not included voice-overs or films as a director.
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1. The Secret Life of Walter Mitty (2013)
PG | 114 min | Adventure, Comedy, Drama
When both he and a colleague are about to lose their job, Walter takes action by embarking on an adventure more extraordinary than anything he ever imagined.
Director: Ben Stiller | Stars: Ben Stiller, Kristen Wiig, Jon Daly, Kathryn Hahn
Votes: 340,749 | Gross: $58.24M
$189 M.
Role - Sean O'Connell
2. Tropic Thunder (2008)
R | 107 min | Action, Comedy, War
Through a series of freak occurrences, a group of actors shooting a big-budget war movie are forced to become the soldiers they are portraying.
Director: Ben Stiller | Stars: Ben Stiller, Jack Black, Robert Downey Jr., Jeff Kahn
Votes: 447,814 | Gross: $110.52M
$188 M.
Role - Himself
3. The Interpreter (2005)
PG-13 | 128 min | Crime, Mystery, Thriller
Political intrigue and deception unfold inside the United Nations, where a U.S. Secret Service agent is assigned to investigate an interpreter who overhears an assassination plot.
Director: Sydney Pollack | Stars: Nicole Kidman, Sean Penn, Catherine Keener, Jesper Christensen
Votes: 110,909 | Gross: $72.71M
$163 M.
Role - Tobin Keller
4. Mystic River (2003)
R | 138 min | Crime, Drama, Mystery
The tragic murder of a 19-year-old girl reunites three childhood friends still living in Boston--the victim's gangster father, a detective, and the disturbed man they both suspect of killing her.
Director: Clint Eastwood | Stars: Sean Penn, Tim Robbins, Kevin Bacon, Emmy Rossum
Votes: 485,696 | Gross: $90.14M
$157 M.
Role - James "Jimmy" Markum
5. The Game (1997)
R | 129 min | Drama, Mystery, Thriller
After a wealthy San Francisco banker is given an opportunity to participate in a mysterious game, his life is turned upside down as he begins to question if it might really be a concealed conspiracy to destroy him.
Director: David Fincher | Stars: Michael Douglas, Deborah Kara Unger, Sean Penn, James Rebhorn
Votes: 429,060 | Gross: $48.32M
$109 M.
Role - Conrad Van Orton
6. Gangster Squad (2013)
R | 113 min | Action, Crime, Drama
It's 1949 Los Angeles, the city is run by gangsters and a malicious mobster, Mickey Cohen. Determined to end the corruption, John O'Mara assembles a team of cops, ready to take down the ruthless leader and restore peace to the city.
Director: Ruben Fleischer | Stars: Sean Penn, Ryan Gosling, Emma Stone, Giovanni Ribisi
Votes: 222,697 | Gross: $46.00M
$105 M.
Role - Mickey Cohen
7. The Thin Red Line (1998)
R | 170 min | Drama, History, War
Adaptation of James Jones' autobiographical 1962 novel, focusing on the conflict at Guadalcanal during the second World War.
Director: Terrence Malick | Stars: Jim Caviezel, Sean Penn, Nick Nolte, Kirk Acevedo
Votes: 199,537 | Gross: $36.40M
$98 M.
Role - 1st Sgt. Welsh
8. I Am Sam (2001)
PG-13 | 132 min | Drama
An intellectually disabled man fights for custody of his 7-year-old daughter and in the process teaches his cold-hearted lawyer the value of love and family.
Director: Jessie Nelson | Stars: Sean Penn, Michelle Pfeiffer, Dakota Fanning, Dianne Wiest
Votes: 155,274 | Gross: $40.31M
$97 M.
Role - Samuel John "Sam" Dawson
9. Dead Man Walking (1995)
R | 122 min | Crime, Drama
A nun, while comforting a convicted killer on death row, empathizes with both the killer and his victim's families.
Director: Tim Robbins | Stars: Susan Sarandon, Sean Penn, Robert Prosky, Raymond J. Barry
Votes: 101,744 | Gross: $39.39M
$83 M.
Role - Matthew Poncelet
10. Carlito's Way (1993)
R | 144 min | Crime, Drama, Thriller
A Puerto Rican former convict, just released from prison, pledges to stay away from drugs and violence despite the pressure around him and lead on to a better life outside of N.Y.C.
Director: Brian De Palma | Stars: Al Pacino, Sean Penn, Penelope Ann Miller, John Leguizamo
Votes: 232,278 | Gross: $36.95M
$64 M.
Role - David Kleinfeld
11. 21 Grams (2003)
R | 124 min | Crime, Drama, Thriller
A freak accident brings together a critically ill mathematician, a grieving mother, and a born-again ex-con.
Director: Alejandro G. Iñárritu | Stars: Sean Penn, Benicio Del Toro, Naomi Watts, Danny Huston
Votes: 245,815 | Gross: $16.29M
$60 M.
Role - Paul Rivers
12. Colors (1988)
R | 120 min | Action, Crime, Drama
An experienced cop and his rookie partner patrol the streets of East Los Angeles while trying to keep the gang violence under control.
Director: Dennis Hopper | Stars: Sean Penn, Robert Duvall, Maria Conchita Alonso, Randy Brooks
Votes: 29,816 | Gross: $46.62M
$60 M.
Role - Officer Danny McGavin
13. Milk (I) (2008)
R | 128 min | Biography, Drama, History
The story of American gay activist Harvey Milk, who fought for gay rights and was elected as California's first openly gay official.
Director: Gus Van Sant | Stars: Sean Penn, Josh Brolin, Emile Hirsch, Diego Luna
Votes: 179,820 | Gross: $31.84M
$55 M.
Role - Harvey Milk
14. The Tree of Life (2011)
PG-13 | 139 min | Drama, Fantasy
The story of a family in Waco, Texas in 1956. The eldest son witnesses the loss of innocence and struggles with his parents' conflicting teachings.
Director: Terrence Malick | Stars: Brad Pitt, Sean Penn, Jessica Chastain, Hunter McCracken
Votes: 184,081 | Gross: $13.30M
$54 M.
Role - Adult Jack
15. Taps (I) (1981)
PG | 126 min | Drama
Military cadets take extreme measures to ensure the future of their academy when its existence is threatened by local condo developers.
Director: Harold Becker | Stars: George C. Scott, Timothy Hutton, Ronny Cox, Sean Penn
Votes: 20,088 | Gross: $35.86M
$35 M.
Role - Cadet Cpt. Alex Dwyer
16. Fast Times at Ridgemont High (1982)
R | 90 min | Comedy, Drama
A group of Southern California high school students are enjoying their most important subjects: sex, drugs and rock n' roll.
Director: Amy Heckerling | Stars: Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Robert Romanus
Votes: 115,682 | Gross: $27.09M
$27 M.
Role - Jeff Spicoli
17. Fair Game (I) (2010)
PG-13 | 108 min | Biography, Drama, Thriller
CIA operative Valerie Plame discovers her identity is allegedly leaked by the government as payback for an op-ed article her husband wrote criticizing the Bush administration.
Director: Doug Liman | Stars: Naomi Watts, Sean Penn, Sonya Davison, Vanessa Chong
Votes: 51,043 | Gross: $9.53M
$24 M.
Role - Joseph Wilson
18. The Gunman (2015)
R | 115 min | Action, Crime, Mystery
A sniper on a mercenary assassination team kills the minister of mines of the Congo. Terrier's successful kill shot forces him into hiding. Returning to the Congo years later, he becomes the target of a hit squad himself.
Director: Pierre Morel | Stars: Sean Penn, Idris Elba, Jasmine Trinca, Javier Bardem
Votes: 43,379 | Gross: $10.64M
$24 M.
Role - Jim Terrier
19. Casualties of War (1989)
R | 113 min | Action, Crime, Drama
During the Vietnam War, a soldier finds himself the outsider of his own squad when they unnecessarily kidnap a female villager.
Director: Brian De Palma | Stars: Michael J. Fox, Sean Penn, Don Harvey, John C. Reilly
Votes: 48,112 | Gross: $18.67M
$19 M.
Role - Sgt. Tony Meserve
20. The Falcon and the Snowman (1985)
R | 131 min | Biography, Crime, Drama
The true story of a disillusioned military contractor employee and his drug pusher childhood friend who became walk-in spies for the Soviet Union.
Director: John Schlesinger | Stars: Timothy Hutton, Sean Penn, Pat Hingle, Joyce Van Patten
Votes: 12,671 | Gross: $17.10M
$17 M.
Role - Daulton Lee
21. This Must Be the Place (2011)
R | 118 min | Adventure, Comedy, Drama
Cheyenne, a retired rock star living off his royalties in Dublin, returns to New York City to find the man responsible for a humiliation suffered by his recently deceased father during W.W.II.
Director: Paolo Sorrentino | Stars: Sean Penn, Frances McDormand, Judd Hirsch, Eve Hewson
Votes: 36,967 | Gross: $0.14M
$12 M.
Role - Cheyenne
22. We're No Angels (1989)
PG-13 | 106 min | Comedy, Crime
Two escaped cons only prayer to escape is to pass themselves off as priests and pass by the police blockade at the border into the safety of Canada.
Director: Neil Jordan | Stars: Robert De Niro, Sean Penn, Demi Moore, Hoyt Axton
Votes: 24,664 | Gross: $10.56M
$11 M.
Role - Jim
23. All the King's Men (2006)
PG-13 | 128 min | Drama, Thriller
Based on the Robert Penn Warren novel. The life of populist Southerner Willie Stark, a political creature loosely based on Governor Huey Long of Louisiana.
Director: Steven Zaillian | Stars: Sean Penn, Jude Law, Kate Winslet, Anthony Hopkins
Votes: 25,581 | Gross: $7.22M
$10 M.
Role - Willie Stark
24. Bad Boys (1983)
R | 123 min | Crime, Drama, Thriller
Chicago crime kid Mick O'Brien is sent to reform school after accidentally killing a rival's kid brother.
Director: Rick Rosenthal | Stars: Sean Penn, Reni Santoni, Jim Moody, Eric Gurry
Votes: 17,050 | Gross: $9.20M
$9 M.
Role - Michael O'Brien
25. Before Night Falls (2000)
R | 133 min | Biography, Drama, Romance
The life of Cuban poet and novelist, Reinaldo Arenas.
Director: Julian Schnabel | Stars: Javier Bardem, Johnny Depp, Olatz López Garmendia, Giovani Florido
Votes: 26,364 | Gross: $4.22M
$9 M.
Role - Cuco Sánchez
26. She's So Lovely (1997)
R | 100 min | Drama, Romance
After being released from a psychiatric institution, a man tries to redeem himself in the eyes of his now-ex wife from the events that led up to his incarceration.
Director: Nick Cassavetes | Stars: Sean Penn, Robin Wright, John Travolta, James Gandolfini
Votes: 8,737 | Gross: $7.22M
$7 M.
Role - Eddie Quinn
27. What Just Happened (2008)
R | 104 min | Comedy, Drama
Two weeks in the life of a fading Hollywood producer who's having a rough time trying to get his new picture made.
Director: Barry Levinson | Stars: Robert De Niro, John Turturro, Stanley Tucci, Sean Penn
Votes: 28,514 | Gross: $1.09M
$7 M.
Role - Himself
28. U Turn (1997)
R | 125 min | Crime, Drama, Thriller
A man heading to Vegas to pay off his gambling debt before the Russian mafia kills him is forced to stop in an Arizona town where everything that can go wrong does go wrong.
Director: Oliver Stone | Stars: Sean Penn, Jennifer Lopez, Nick Nolte, Billy Bob Thornton
Votes: 54,753 | Gross: $6.63M
$7 M.
Role - Bobby Cooper
29. The Assassination of Richard Nixon (2004)
R | 95 min | Biography, Crime, Drama
Based on real life events, Assassination is set in 1974 and centers on a businessman who decides to take extreme measures to achieve his American dream.
Director: Niels Mueller | Stars: Sean Penn, Naomi Watts, Don Cheadle, Jack Thompson
Votes: 26,109 | Gross: $0.70M
$4 M.
Role - Samuel J. Bicke
30. Sweet and Lowdown (1999)
PG-13 | 95 min | Comedy, Drama, Music
In the 1930s, jazz guitarist Emmet Ray idolizes Django Reinhardt, faces gangsters and falls in love with a mute woman.
Director: Woody Allen | Stars: Sean Penn, Samantha Morton, Woody Allen, Ben Duncan
Votes: 36,662 | Gross: $4.20M
$4 M.
Role - Emmet Ray
31. Shanghai Surprise (1986)
PG-13 | 97 min | Adventure, Comedy, Crime
Shanghai, 1938: A missionary woman hires a fortune hunter to help her find 1100 lbs. opium lost, as wounded need the morphine. Adventure and romance follows.
Director: Jim Goddard | Stars: Sean Penn, Madonna, Paul Freeman, Richard Griffiths
Votes: 5,765 | Gross: $2.32M
$2 M.
Role - Glendon Wasey
32. At Close Range (1986)
R | 111 min | Crime, Drama
Reunited with his career criminal father, tough teen Brad thinks he's found his ticket to an exciting life of crime, only to find out he's wrong.
Director: James Foley | Stars: Sean Penn, Christopher Walken, Mary Stuart Masterson, Chris Penn
Votes: 17,726 | Gross: $2.35M
$2 M.
Role - Brad Whitewood Jr.
33. State of Grace (1990)
R | 134 min | Action, Crime, Drama
A New York cop is recruited to return to his hometown and infiltrate the mob ran by his best friend's brother.
Director: Phil Joanou | Stars: Sean Penn, Ed Harris, Gary Oldman, Robin Wright
Votes: 24,765 | Gross: $1.91M
$2 M.
Role - Terry Noonan
34. Hurlyburly (1998)
R | 122 min | Comedy, Drama
Hollywood movers and shakers dissect their own personal lives when everything seems to clash together.
Director: Anthony Drazan | Stars: Sean Penn, Kevin Spacey, Chazz Palminteri, Robin Wright
Votes: 10,454 | Gross: $1.80M
$2 M.
Role - Eddie
35. The Weight of Water (2000)
R | 114 min | Crime, Drama, Mystery
A newspaper photographer researches an 1873 double homicide and finds her own life paralleling that of a witness who survived the tragic ordeal.
Director: Kathryn Bigelow | Stars: Catherine McCormack, Sean Penn, Sarah Polley, Elizabeth Hurley
Votes: 10,035 | Gross: $0.10M
$0 M.
Role - Thomas Janes
36. Hugo Pool (1997)
R | 92 min | Comedy, Romance
An LA pool cleaner/Alyssa Milano falls in love with a young man with ALS/Lou Gehrig's Disease.
Director: Robert Downey Sr. | Stars: Alyssa Milano, Mark Boone Junior, Malcolm McDowell, Brendan Dawson
Votes: 2,097 | Gross: $0.00M
$0 M.
Role - Strange Hitchhiker
37. Pauly Shore Is Dead (2003)
R | 82 min | Comedy
Hollywood's Pauly Shore loses everything, fakes his own death, and gets caught.
Directors: Adam Freeman, Pauly Shore | Stars: Ashley L. Anderson, Pamela Anderson, Camille Anderson, Beaumont Bacon
Votes: 5,013
$0 M.
Role - Himself
38. Crackers (1984)
PG | 91 min | Adventure, Comedy, Crime
Reduced to minding the counter at a crusty pawn shop, Weslake tumbles onto a scheme by some disgruntled misfit clients to rob the place. Rather than blow the whistle, however, he insinuates himself as the heist's mastermind.
Director: Louis Malle | Stars: Donald Sutherland, Jack Warden, Sean Penn, Wallace Shawn
Votes: 1,544 | Gross: $0.13M
N/A
Role - Dillard
39. Up at the Villa (2000)
PG-13 | 115 min | Drama, Romance
A widow finds choosing a new husband might not be her choice at all, as the actions of her various prospects confine her freedom.
Director: Philip Haas | Stars: Kristin Scott Thomas, Sean Penn, Anne Bancroft, James Fox
Votes: 2,845 | Gross: $2.93M
N/A
Role - Rowley Flint
40. It's All About Love (2003)
R | 106 min | Drama, Romance, Sci-Fi
Two lovers attempt to save their relationship in a near-future world on the brink of cosmic collapse.
Director: Thomas Vinterberg | Stars: Joaquin Phoenix, Claire Danes, Sean Penn, Douglas Henshall
Votes: 9,866 | Gross: $0.01M
N/A
Role - Marciello
41. Loved (1997)
PG-13 | 109 min | Drama, Thriller
After a husband is accused of driving his third wife to suicide, his first wife Hedda, a troubled woman who can't hate or hurt others even if they had wronged her, is subpoenaed to testify on his abusive behavior during their marriage.
Director: Erin Dignam | Stars: Robin Wright, William Hurt, Sean Penn, Evelyn Dignam
Votes: 742
N/A
Role - Michael
42. Judgment in Berlin (1988)
PG | 96 min | Drama
American judge in Germany must decide if the hijacking of an East German plane into West Berlin was justified.
Director: Leo Penn | Stars: Martin Sheen, Sam Wanamaker, Max Gail, Jürgen Heinrich
Votes: 884 | Gross: $0.23M
N/A
Role - Guenther X
43. Racing with the Moon (1984)
PG | 108 min | Comedy, Drama, Romance
In 1942 California, two young men await induction into the U.S. Marines and say goodbye to their girlfriends.
Director: Richard Benjamin | Stars: Sean Penn, Elizabeth McGovern, Nicolas Cage, John Karlen
Votes: 5,246 | Gross: $6.05M
$6 M.
Role - Henry "Hopper" Nash
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