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1. Witch Hunt (2008)
directed by Dana Nachman, Don Hardy
featuring Sean Penn
Academy Award-winner Sean Penn serves as producer and narrator of this documentary detailing the disturbing spike in child-molestation allegations ... More
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2. War Made Easy: How Presidents & Pundits Keep Spinning Us to Death (2007)
directed by Jeremy Earp, Loretta Alper
featuring Norman Solomon, Sean Penn
Author Norman Soloman teams with activist/actor Sean Penn to encourage critical thinking about media spin during wartime by introducing viewers to ... More
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3. Deflating the Elephant: The Framed Messages Behind Conservative Dialogue (2009)
directed by Aldo Vidali
featuring George Lakoff, Sean Penn
Discover how language impacts our lives and our political discourse in this documentary featuring Academy Award-winner Sean Penn. When we speak, ... More
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4. The Thin Red Line (1998)
directed by Terrence Malick
featuring Sean Penn, Adrien Brody, James Caviezel, Ben Chaplin, George Clooney
The return of director Terrence Malick to feature filmmaking after a twenty year sabbatical, this World War II drama is an elegiac rumination on man ... More
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5. Shanghai Surprise (1986)
directed by Jim Goddard
featuring Sean Penn, Madonna, Paul Freeman, Philip Sayer
Madonna and Sean Penn, who were husband and wife at the time, starred in this notorious box-office bomb that one critic termed "Flop Suey." The film ... More
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6. I Am Sam (2001)
directed by Jessie Nelson
featuring Sean Penn, Michelle Pfeiffer, Dakota Fanning
Sean Penn stars in this drama as Sam Dawson, a developmentally disabled adult who has been working at a coffee shop and raising his daughter Lucy ... More
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7. She's So Lovely (1997)
directed by Nick Cassavetes
featuring Sean Penn, Robin Wright Penn, John Travolta
Written by the late John Cassavettes in 1987 and filmed by his son Nick a decade later, the comic drama She's So Lovely (originally and more ... More
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8. Milk (2008)
directed by Gus Van Sant
featuring Sean Penn, Emile Hirsch, Josh Brolin, Diego Luna, James Franco
Academy Award winner Sean Penn takes the title role in Gus Van Sant's biopic tracing the last eight years in the life of Harvey Milk, the ill-fated ... More
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9. Persepolis (2007)
directed by Marjane Satrapi, Vincent Paronnaud
featuring Chiara Mastroianni, Catherine Deneuve, Gena Rowlands, Sean Penn, Iggy Pop
Filmmakers Vincent Paronnaud and Marjane Satrapi collaborated to co-write and co-direct this adaptation of Satrapi's bestselling autobiographical ... More
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10. The Interpreter (2005)
directed by Sydney Pollack
featuring Nicole Kidman, Sean Penn, Catherine Keener, Jesper Christensen, Yvan Attal
An overheard conversation leads a woman into a dark world of deadly intrigue in this political thriller. Silvia Broome (Nicole Kidman) is an African ... More
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11. Fair Game (2010)
directed by Doug Liman
featuring Naomi Watts, Sean Penn, Bruce McGill, Michael Kelly, Ty Burrell
The Bourne Identity director Doug Liman teams with screenwriters Jez Butterworth and John-Henry Butterworth to streamline Joseph Wilson's and Valerie ... More
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12. All the King's Men (2006)
directed by Steven Zaillian
featuring Sean Penn, Jude Law, Kate Winslet, James Gandolfini, Mark Ruffalo
The legacy of a populist Southern politician whose lofty ambitions for the future leave him open to corruption and scandal is detailed as author ... More
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13. State of Grace (1990)
directed by Phil Joanou
featuring Sean Penn, Ed Harris, Gary Oldman, Robin Wright, John Turturro
This directorial effort from Phil Joanou stars Sean Penn as an Irish-American undercover cop working the Hell's Kitchen beat. Penn is ostensibly on a ... More
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14. Bad Boys (1983)
directed by Rick Rosenthal
featuring Sean Penn, Reni Santoni, Esai Morales, Eric Gurry, Jim Moody
Following magnetic performances in Taps (1981) and Fast Times at Ridgemont High (1982), young actor Sean Penn sealed his reputation as one of his ... More
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15. Dogtown and Z-Boys (2002)
directed by Stacy Peralta
featuring Henry Rollins, Stacy Peralta, Tony Hawk, Sean Penn
In the mid-'70s, skateboarding was widely seen as a fad of the 1960s that had all but died out, except for a handful of committed fans in California. ... More
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16. Racing with the Moon (1984)
directed by Richard Benjamin
featuring Sean Penn, Elizabeth McGovern, Nicolas Cage, John Karlen, Rutanya Alda
Sean Penn graduated to full stardom with the 1984 drama Racing with the Moon, even though the film itself hardly set new box office records. Set in ... More
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17. The Game (1997)
directed by David Fincher
featuring Michael Douglas, Sean Penn, Deborah Kara Unger, James Rebhorn, Peter Donat
Director David Fincher followed the success of his dark and atmospheric crime thriller Seven (1995) with another exercise in stylish film noir, this ... More
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18. Gangster Squad (2013)
directed by Ruben Fleischer
featuring Sean Penn, Ryan Gosling, Josh Brolin, Emma Stone, Anthony Mackie, Michael Peņa
An elite police squad fights to save the city of Los Angeles from a power-hungry East Coast mobster in this gritty police-detective film set in the ... More
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19. Fast Times at Ridgemont High (1982)
directed by Amy Heckerling
featuring Sean Penn, Jennifer Jason Leigh, Judge Reinhold, Robert Romanus, Brian Backer, Phoebe Cates, Ray Walston
Amy Heckerling's adaptation of Cameron Crowe's Fast Times at Ridgemont High is often considered one of the finest films of a disreputable genre (the ... More
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20. It's All About Love (2004)
directed by Thomas Vinterberg
featuring Joaquin Phoenix, Claire Danes, Sean Penn, Douglas Henshall, Alun Armstrong
An estranged couple are brought back together as they run for their lives in a future world where science as well as emotions have gone haywire in ... More
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21. The Tree of Life (2011)
directed by Terrence Malick
featuring Brad Pitt, Sean Penn, Jessica Chastain, Hunter McCracken, Laramie Eppler, Tye Sheridan
The eldest son of a 1950s-era Midwestern family sets out on an existential journey that leads him to question his faith while seeking the answers to ... More
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22. Crackers (1984)
directed by Louis Malle
featuring Donald Sutherland, Jack Warden, Sean Penn, Wallace Shawn, Larry Riley
A remake of Pigeon by Mario Monicelli, but set on the streets of San Francisco in a contemporary America instead of Italy in the '50s, this comedy ... More
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23. The Falcon and the Snowman (1985)
directed by John Schlesinger
featuring Timothy Hutton, Sean Penn, David Suchet, Lori Singer, Pat Hingle
John Schlesinger directed this fact-based drama - adapted from Robert Lindsay's bestseller of the same title -- about two Californians, friends since ... More
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24. The Weight of Water (2002)
directed by Kathryn Bigelow
featuring Catherine McCormack, Sarah Polley, Sean Penn, Josh Lucas, Elizabeth Hurley
A woman studying a crime of the past finds her own life becoming a morass of suspicion and deceit in this drama based on the novel by Anita Shreve. ... More
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25. Colors (1988)
directed by Dennis Hopper
featuring Sean Penn, Robert Duvall, Maria Conchita Alonso, Randy Brooks, Grand L. Bush
Colors stars Robert Duvall and Sean Penn as partners on the LAPD's gang crime division. Duvall had hoped to spend more time with his family, but he's ... More
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