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The Best Movies Starring Sean Penn

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1

Fast Times at Ridgemont High 1982, 90 min.

Amy Heckerling • Starring: Sean Penn, Jennifer Jason Leigh, Judge Reinhold

Comedy • Comedy Drama • Coming-of-Age

Held position in the past 45 days

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2

The Game 1997, 128 min.

David Fincher • Starring: Michael Douglas, Sean Penn, Deborah Kara Unger

Mindbender • Mystery • Paranoid Thriller

Held position in the past 45 days

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3

The Tree of Life 2011, 138 min.

Terrence Malick • Starring: Brad Pitt, Sean Penn, Jessica Chastain

Childhood Drama • Drama • Family Drama

Up by 1 in the past 45 days

1

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4

Mystic River 2003, 137 min.

Clint Eastwood • Starring: Sean Penn, Kevin Bacon, Tim Robbins

Based-on-21st-Century-Literature • Drama • Mystery

Held position in the past 45 days

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5

Milk 2008, 128 min.

Gus Van Sant • Starring: Sean Penn, Emile Hirsch, Josh Brolin

Based-on-a-True-Story • Biopic • Drama

Held position in the past 45 days

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6

Carlito's Way 1993, 141 min.

Brian De Palma • Starring: Sean Penn, Penelope Ann Miller, John Leguizamo

Crime Drama • Crime • Drama

Held position in the past 45 days

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7

The Thin Red Line 1998, 170 min.

Terrence Malick • Starring: Sean Penn, Nick Nolte, Jim Caviezel

Anti-War Film • Based-on-20th-Century-Literature • Combat Films

Held position in the past 45 days

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8

Dead Man Walking 1995, 122 min.

Tim Robbins • Starring: Susan Sarandon, Sean Penn, Robert Prosky

Crime Drama • Crime • Drama

Down by 2 in the past 45 days

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9

Sweet and Lowdown 1999, 95 min.

Woody Allen • Starring: Sean Penn, Samantha Morton, Anthony LaPaglia

Comedy Drama • Mockumentary • Tragi-comedy

Held position in the past 45 days

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10

Casualties of War 1989, 121 min.

Brian De Palma • Starring: Sean Penn, Michael J. Fox, John C. Reilly

Anti-War Film • Based-on-20th-Century-Literature • Based-on-a-True-Story

Up by 1 in the past 45 days

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11

21 Grams 2003, 124 min.

Alejandro González Iñárritu • Starring: Sean Penn, Naomi Watts, Danny Huston

Anthology Film • Crime Drama • Crime Thriller

Held position in the past 45 days

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12

Taps 1981, 126 min.

Harold Becker • Starring: George C. Scott, Timothy Hutton, Sean Penn

Drama • Action • Teen Movie

Up by 4 in the past 45 days

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13

State of Grace 1990, 134 min.

Phil Joanou • Starring: Sean Penn, Gary Oldman, Robin Wright

Crime Thriller • Crime • Gangster Film

Up by 22 in the past 45 days

22

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14

The Secret Life of Walter Mitty 2013, 125 min.

Ben Stiller • Starring: Ben Stiller, Kristen Wiig, Patton Oswalt

Adventure • Adventure Drama • Comedy Drama

Down by 1 in the past 45 days

1

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15

Colors 1988, 120 min.

Dennis Hopper • Starring: Sean Penn, Robert Duvall, Maria Conchita Alonso

Action • Buddy Film • Crime Drama

Held position in the past 45 days

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16

Bad Boys 1983, 123 min.

Rick Rosenthal • Starring: Sean Penn, Reni Santoni, Esai Morales

Crime • Crime Drama • Drama

Held position in the past 45 days

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17

The Falcon and the Snowman 1985, 131 min.

John Schlesinger • Starring: Timothy Hutton, Sean Penn, Pat Hingle

Docudrama • Drama • Spy Film

Up by 2 in the past 45 days

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18

Dogtown and Z-Boys 2001, 91 min.

Stacy Peralta • Starring: Sean Penn, Jay Adams, Jeff Ament

Biography • Documentary • Social History

Held position in the past 45 days

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19

I Am Sam 2001, 132 min.

Jessie Nelson • Starring: Sean Penn, Michelle Pfeiffer, Dakota Fanning

Courtroom Drama • Drama • Female-Directed Film

Up by 1 in the past 45 days

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20

U Turn 1997, 125 min.

Oliver Stone • Starring: Sean Penn, Billy Bob Thornton, Jon Voight

Black Comedy • Crime Thriller • Crime

Down by 1 in the past 45 days

1

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