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Sean Penn
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| Sean Penn | | Mystic River (2003) |
| Sean Penn | | I Am Sam (2001) |
| Sean Penn | | Dead Man Walking (1995) |
| The Thin Red Line (1998) | | James Caviezel, Sean Penn and George Clooney |
Directed by Terrence Malick
| Carlito's Way (1993) | | Al Pacino, Sean Penn and Penelope Ann Miller |
Director: Brian De Palma
| It’s All About Love (2003) | | Joaquin Phoenix, Claire Danes and Sean Penn |
Director: Thomas Vinterberg
| The Interpreter (2005) | | Nicole Kidman, Sean Penn and Catherine Keener |
Director: Sydney Pollack
| Sean Penn | | Jerry Lee Lewis in Great Balls of Fire! (1989) |
Dennis Quaid got the part
| Willie Stark | | Broderick Crawford & Sean Penn |
Broderick Crawford - All the King's Men (1949), Sean Penn - All the King's Men (2006)
| Sean Penn | | Milk (2008) |
The story of California's first openly gay elected official, Harvey Milk, a San Francisco supervisor who was assassinated along with Mayor George Moscone by San Francisco Supervisor Dan White.
| Sean Penn | | Dead Man Walking |
1995 - Best Male Lead
| Sean Penn | | Mystic River |
Best Actor - Drama, 2003
| Fast Times at Ridgemont High (1982) | | Sean Penn, Judge Reinhold and Phoebe Cates |
"All I need are some tasty waves, a cool buzz, and I'm fine."
| Sweet and Lowdown (1999) | | Sean Penn, Samantha Morton and Uma Thurman |
A Woody Allen Film
| All the King's Men (2006) | | Sean Penn, Jude Law, Anthony Hopkins and Kate Winslet |
Director: Steven Zaillian
| Dead Man Walking (1995) | | Sean Penn, Susan Sarandon and Robert Prosky |
Director: Tim Robbins
| I Am Sam (2001) | | Sean Penn, Michelle Pfeiffer and Dakota Fanning |
Director: Jessie Nelson
| Milk (2008) | | Sean Penn, Emile Hirsch and Josh Brolin |
IMDB:8.1/10. Director: Gus Van Sant. 8 Oscar nominations (winners not yet announced) and 4 Bafta nominations (winners not yet announced)
| Mystic River (2003) | | Sean Penn, Tim Robbins and Kevin Bacon |
Director: Clint Eastwood
| Fast Times at Ridgemont High (1982) | | Sean Penn, Jennifer Jason Leigh and Judge Reinhold |
Director: Amy Heckerling. Also starred Phoebe Cates, Ray Walston, Forest Whitaker and Vincent Schiavelli
| The Assassination of Richard Nixon (2004) | | Sean Penn, Naomi Watts and Don Cheadle |
Director: Niels Mueller