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Top Sean Penn movies (based on box office success and rating)

| # | Year | | Movie name |
Director | Cast |
|---|
| 1 |
2003 |
 |
Mystic River |
Clint Eastwood |
Tim Robbins,Sean Penn,Kevin Bacon,Laurence Fishburne,Laura Linney,Marcia Gay Harden,Emmy Rossum,Eli Wallach,Kevin Chapman,Tom Guiry |
| 2 |
2003 |
 |
21 Grams |
Alejandro González Iñárritu |
Naomi Watts,Sean Penn,Benicio Del Toro,Danny Huston,Charlotte Gainsbourg,Clea DuVall,Eddie Marsan,Melissa Leo,Carly Nahon,Denis O'Hare |
| 3 |
1997 |
 |
The Game |
David Fincher |
Sean Penn,Michael Douglas,Deborah Kara Unger,James Rebhorn,Carroll Baker,Armin Mueller-Stahl,Peter Donat,Mark Boone Junior,Anna Katarina,Tommy Flanagan |
| 4 |
1998 |
 |
The Thin Red Line |
Terrence Malick |
John Travolta,Sean Penn,George Clooney,John Cusack,Woody Harrelson,Adrien Brody,John C. Reilly,Nick Nolte,James Caviezel,Elias Koteas |
| 5 |
2008 |
 |
Milk |
Gus Van Sant |
Sean Penn,Josh Brolin,James Franco,Emile Hirsch,Diego Luna,Denis O'Hare,Victor Garber,Alison Pill,Peter Jason,Joseph Cross |
| 6 |
1993 |
 |
Carlito's Way |
Brian De Palma |
Al Pacino,Sean Penn,John Leguizamo,Luis Guzmán,Viggo Mortensen,Penelope Ann Miller,James Rebhorn,John Ortiz,Ingrid Rogers,Joseph Siravo |
| 7 |
2001 |
 |
I Am Sam |
Jessie Nelson |
Michelle Pfeiffer,Sean Penn,Dianne Wiest,Dakota Fanning,Laura Dern,Mary Steenburgen,Loretta Devine,Richard Schiff,Brent Spiner,Doug Hutchison |
| 8 |
1982 |
 |
Fast Times at Ridgemont High |
Amy Heckerling |
Nicolas Cage,Jennifer Jason Leigh,Sean Penn,Forest Whitaker,Judge Reinhold,Eric Stoltz,James Russo,Phoebe Cates,Ray Walston,Vincent Schiavelli |
| 9 |
2005 |
 |
The Interpreter |
Sydney Pollack |
Nicole Kidman,Sean Penn,Catherine Keener,Jesper Christensen,Yvan Attal,Sydney Pollack,George Harris,Clyde Kusatsu,Tsai Chin,Earl Cameron |
| 10 |
1995 |
 |
Dead Man Walking |
Tim Robbins |
Susan Sarandon,Sean Penn,Jack Black,R. Lee Ermey,Raymond J. Barry,Robert Prosky,Celia Weston,Lois Smith,Scott Wilson,Clancy Brown |
| 11 |
1997 |
 |
U Turn |
Oliver Stone |
Sean Penn,Jon Voight,Billy Bob Thornton,Nick Nolte,Claire Danes,Jennifer Lopez,Liv Tyler,Joaquin Phoenix,Powers Boothe,Julie Hagerty |
| 12 |
2004 |
 |
The Assassination of Richard Nixon |
Niels Mueller |
Naomi Watts,Sean Penn,Don Cheadle,Michael Wincott,Jack Thompson,Mykelti Williamson,Nick Searcy,April Grace,Brad William Henke,Russell Means |
| 13 |
1989 |
 |
Casualties of War |
Brian De Palma |
Sean Penn,John Leguizamo,John C. Reilly,Michael J. Fox,Ving Rhames,Amy Irving,Don Harvey,Stephen Baldwin,Dale Dye,Sam Robards |
| 14 |
1999 |
 |
Being John Malkovich |
Spike Jonze |
Cameron Diaz,John Cusack,Brad Pitt,Dustin Hoffman,Catherine Keener,Winona Ryder,John Malkovich,Mary Kay Place,Sean Penn,Ned Bellamy |
| 15 |
2006 |
 |
All the King's Men |
Steven Zaillian |
Anthony Hopkins,Kate Winslet,Sean Penn,Jude Law,Patricia Clarkson,Mark Ruffalo,James Gandolfini,Kathy Baker,Kevin Dunn,Frederic Forrest |
| 16 |
1988 |
 |
Colors |
Dennis Hopper |
Robert Duvall,Sean Penn,Don Cheadle,Seymour Cassel,Maria Conchita Alonso,Tony Todd,Glenn Plummer,Damon Wayans,Grand L. Bush,Jack Nance |
| 17 |
1990 |
 |
State of Grace |
Phil Joanou |
Gary Oldman,Ed Harris,Sean Penn,John Turturro,Robin Wright,John C. Reilly,Burgess Meredith,James Russo,Deirdre O'Connell,Joe Viterelli |
| 18 |
1999 |
 |
Sweet and Lowdown |
Woody Allen |
Uma Thurman,Sean Penn,Woody Allen,Samantha Morton,Anthony LaPaglia,Gretchen Mol,Denis O'Hare,Brad Garrett,Chris Bauer,Tony Darrow |
| 19 |
1989 |
 |
We're No Angels |
Neil Jordan |
Robert De Niro,Sean Penn,Demi Moore,John C. Reilly,Wallace Shawn,James Russo,Bruno Kirby,Jay Brazeau,Hoyt Axton,Frank C. Turner |
| 20 |
1986 |
 |
At Close Range |
James Foley |
Christopher Walken,Sean Penn,Kiefer Sutherland,David Strathairn,Crispin Glover,Chris Penn,Mary Stuart Masterson,Tracey Walter,Candy Clark,Anna Levine |
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