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1
Amy Heckerling • Starring: Sean Penn, Jennifer Jason Leigh, Judge Reinhold
Comedy • Comedy Drama • 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
Drama • Family Drama • Fantasy
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
Vincent Paronnaud, Marjane Satrapi • Starring: Gena Rowlands, Gabrielle Lopes, Simon Abkarian
Animation • Based-on-a-True-Story • Based-on-Comics
8
Terrence Malick • Starring: Sean Penn, Nick Nolte, Jim Caviezel
Anti-War Film • Based-on-20th-Century-Literature • Combat Films
9
Tim Robbins • Starring: Susan Sarandon, Sean Penn, Robert Prosky
10
Woody Allen • Starring: Sean Penn, Samantha Morton, Anthony LaPaglia
Comedy Drama • Mockumentary • Tragi-comedy
11
Brian De Palma • Starring: Sean Penn, John Leguizamo, Thuy Thu Le
War • Drama • Anti-War Film
12
Alejandro González Iñárritu • Starring: Sean Penn, Naomi Watts, Danny Huston
Anthology Film • Crime Drama • Crime Thriller
13
Harold Becker • Starring: George C. Scott, Timothy Hutton, Sean Penn
Drama • Action • Teen Movie
14
Phil Joanou • Starring: Sean Penn, Gary Oldman, Robin Wright
Crime Thriller • Crime • Gangster Film
15
Ben Stiller • Starring: Ben Stiller, Kristen Wiig, Patton Oswalt
Adventure • Adventure Drama • Comedy Drama
16
Dennis Hopper • Starring: Sean Penn, Robert Duvall, Maria Conchita Alonso
Action • Buddy Film • Crime Drama
17
Rick Rosenthal • Starring: Sean Penn, Reni Santoni, Esai Morales
Crime • Crime Drama • Drama
18
John Schlesinger • Starring: Timothy Hutton, Sean Penn, Pat Hingle
Docudrama • Drama • Spy Film
19
Stacy Peralta • Starring: Sean Penn, Jay Adams, Jeff Ament
Biography • Documentary • Social History
20
Jessie Nelson • Starring: Sean Penn, Michelle Pfeiffer, Dakota Fanning
Courtroom Drama • Drama • Female-Directed Film
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