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1. Mystic River
Year:2003, Director:Clint Eastwood
Cast:Kevin Bacon, Laurence Fishburne, Sean Penn, Marcia Gay Harden, Tim Robbins, Laura Linney
Language:English
Category:Drama, Thriller
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2. Milk
Year:2008, Director:Gus Van Sant
Cast:James Franco, Sean Penn, Josh Brolin, Diego Luna, Emile Hirsch, Alison Pill
Language:English
Category:Drama, History
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3. 21 Grams
Year:2003, Director:Alejandro González Iñárritu
Cast:Sean Penn, Danny Huston, Benicio Del Toro, Naomi Watts, Carly Nahon, Claire Pakis
Language:English
Category:Drama, Thriller
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4. Dead Man Walking
Year:1995, Director:Tim Robbins
Cast:Susan Sarandon, Sean Penn, Raymond J. Barry, R. Lee Ermey, Celia Weston, Robert Prosky
Language:English
Category:Drama, Crime
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5. Carlito's Way
Year:1993, Director:Brian De Palma
Cast:Al Pacino, John Leguizamo, Luis Guzmán, Sean Penn, Penelope Ann Miller, Ingrid Rogers
Language:English
Category:Drama, Thriller
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6. The Game
Year:1997, Director:David Fincher
Cast:Sean Penn, Carroll Baker, Michael Douglas, Deborah Kara Unger, James Rebhorn, Peter Donat
Language:English
Category:Drama, Thriller
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7. Fast Times at Ridgemont High
Year:1982, Director:Amy Heckerling
Cast:Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Phoebe Cates, Robert Romanus, Brian Backer
Language:English
Category:Drama, Comedy
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8. State of Grace
Year:1990, Director:Phil Joanou
Cast:Burgess Meredith, Ed Harris, John Turturro, Gary Oldman, Sean Penn, Robin Wright
Language:English
Category:Drama, Thriller
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9. The Thin Red Line
Year:1998, Director:Terrence Malick
Cast:Nick Nolte, Sean Penn, Elias Koteas, Jim Caviezel, Dash Mihok, Ben Chaplin
Language:English
Category:Drama, War
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10. I Am Sam
Year:2001, Director:Jessie Nelson
Cast:Sean Penn, Michelle Pfeiffer, Richard Schiff, Loretta Devine, Dianne Wiest, Dakota Fanning
Language:English
Category:Drama
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11. The Tree of Life
Year:2011, Director:Terrence Malick
Cast:Brad Pitt, Sean Penn, Jessica Chastain, Hunter McCracken, Laramie Eppler, Tye Sheridan
Language:English
Category:Drama, Fantasy
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12. Casualties of War
Year:1989, Director:Brian De Palma
Cast:John Leguizamo, John C. Reilly, Sean Penn, Michael J. Fox, Don Harvey, Thuy Thu Le
Language:English
Category:Drama, War
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13. At Close Range
Year:1986, Director:James Foley
Cast:Christopher Walken, Sean Penn, Chris Penn, Mary Stuart Masterson, Millie Perkins, Eileen Ryan
Language:English
Category:Drama, Romantic
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14. U Turn
Year:1997, Director:Oliver Stone
Cast:Billy Bob Thornton, Jon Voight, Sean Penn, Jennifer Lopez, Abraham Benrubi, Richard Rutowski
Language:English
Category:Drama, Thriller
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15. This Must Be the Place
Year:2011, Director:Paolo Sorrentino
Cast:Harry Dean Stanton, Sean Penn, Frances McDormand, Judd Hirsch, Kerry Condon, Eve Hewson
Language:English
Category:Drama, Comedy
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16. Colors
Year:1988, Director:Dennis Hopper
Cast:Robert Duvall, Sean Penn, Don Cheadle, Maria Conchita Alonso, Grand L. Bush, Randy Brooks
Language:English
Category:Drama, Romantic
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17. The Falcon and the Snowman
Year:1985, Director:John Schlesinger
Cast:Sean Penn, Pat Hingle, Timothy Hutton, Joyce Van Patten, Rob Reed, Rob Newell
Language:English
Category:Drama, Thriller
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18. The Assassination of Richard Nixon
Year:2004, Director:Niels Mueller
Cast:Sean Penn, Jack Thompson, Don Cheadle, Naomi Watts, Brad William Henke, Nick Searcy
Language:English
Category:Drama, Biography
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19. The Interpreter
Year:2005, Director:Sydney Pollack
Cast:Nicole Kidman, Sean Penn, Catherine Keener, Jesper Christensen, Yvan Attal, Earl Cameron
Language:Aboriginal
Category:Thriller, Mystery
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20. Bad Boys
Year:1983, Director:Rick Rosenthal
Cast:Sean Penn, Clancy Brown, Esai Morales, Reni Santoni, Jim Moody, Eric Gurry
Language:English
Category:Drama, Thriller
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21. Sweet and Lowdown
Year:1999, Director:Woody Allen
Cast:Woody Allen, Sean Penn, Dan Moran, Tony Darrow, Daniel Okrent, Ben Duncan
Language:English
Category:Drama, Comedy
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22. All the King's Men
Year:2006, Director:Steven Zaillian
Cast:Anthony Hopkins, Jude Law, Sean Penn, Patricia Clarkson, Mark Ruffalo, Kate Winslet
Language:English
Category:Drama, Thriller
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23. Taps
Year:1981, Director:Harold Becker
Cast:Sean Penn, George C. Scott, Timothy Hutton, Tom Cruise, Ronny Cox, Brendan Ward
Language:English
Category:Drama
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24. Fair Game
Year:2010, Director:Doug Liman
Cast:Sean Penn, Naomi Watts, Anand Tiwari, Vanessa Chong, Stephanie Chai, Sonya Davison
Language:English
Category:Drama, Thriller
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25. We're No Angels
Year:1989, Director:Neil Jordan
Cast:Robert De Niro, Sean Penn, Demi Moore, Bruno Kirby, Hoyt Axton, Ray McAnally
Language:English
Category:Comedy, Crime
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1. The Tree of Life
Year:2011, Director:Terrence Malick
Cast:Brad Pitt, Sean Penn, Jessica Chastain, Hunter McCracken, Laramie Eppler, Tye Sheridan
Language:English
Category:Drama, Fantasy
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2. Fair Game
Year:2010, Director:Doug Liman
Cast:Sean Penn, Naomi Watts, Anand Tiwari, Vanessa Chong, Stephanie Chai, Sonya Davison
Language:English
Category:Drama, Thriller
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3. This Must Be the Place
Year:2011, Director:Paolo Sorrentino
Cast:Harry Dean Stanton, Sean Penn, Frances McDormand, Judd Hirsch, Kerry Condon, Eve Hewson
Language:English
Category:Drama, Comedy
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4. I'm Still Here
Year:2010, Director:Casey Affleck
Cast:Jack Nicholson, Joaquin Phoenix, Casey Affleck, Antony Langdon, Carey Perloff, Larry McHale
Language:English
Category:Drama, Comedy
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