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1
Amy Heckerling • Starring: Sean Penn, Jennifer Jason Leigh, Judge Reinhold
Comedy Drama • Comedy • Coming-of-Age
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2
David Fincher • Starring: Michael Douglas, Sean Penn, Deborah Kara Unger
Mindbender • Mystery • Paranoid Thriller
3
Terrence Malick • Starring: Brad Pitt, Sean Penn, Jessica Chastain
Childhood Drama • Drama • Family Drama
4
Clint Eastwood • Starring: Sean Penn, Kevin Bacon, Tim Robbins
Based-on-21st-Century-Literature • Drama • Mystery
5
Gus Van Sant • Starring: Sean Penn, Emile Hirsch, Josh Brolin
Based-on-a-True-Story • Biopic • Drama
6
Brian De Palma • Starring: Sean Penn, Penelope Ann Miller, John Leguizamo
Crime Drama • Crime • Drama
7
Terrence Malick • Starring: Sean Penn, Nick Nolte, Jim Caviezel
Anti-War Film • Based-on-20th-Century-Literature • Combat Films
8
Woody Allen • Starring: Sean Penn, Samantha Morton, Anthony LaPaglia
Comedy Drama • Mockumentary • Tragi-comedy
9
Tim Robbins • Starring: Susan Sarandon, Sean Penn, Robert Prosky
10
Paul Thomas Anderson • Starring: Alana Haim, Cooper Hoffman, Sean Penn
Absurd Comedy • Comedy Drama • Comedy
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