film The Best Sean Penn Movies  

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List Rules Vote for your favorite movies, regardless of critic reviews or how big the role was.

List of the best Sean Penn movies, ranked best to worst with movie trailers when available. Sean Penn's highest grossing movies have received a lot of accolades over the years, earning millions upon millions around the world. The order of these top Sean Penn movies is decided by how many votes they receive, so only highly rated Sean Penn movies will be at the top of the list. Sean Penn has been in a lot of films, so people often debate each other over what the greatest Sean Penn movie of all time is. If you and a friend are arguing about this then use this list of the most entertaining Sean Penn films to end the squabble once and for all.

If you think the best Sean Penn role isn't at the top, then upvote it so it has the chance to become number one. The greatest Sean Penn performances didn't necessarily come from the best movies, but in most cases they go hand in hand.

List films include Up at the Villa, This So-Called Disaster and many more.

"This list answers the questions, "What are the best Sean Penn movies?" and "What are the greatest Sean Penn roles of all time?"

Notable directors that have worked with Sean Penn include names like Brian De Palma, Terrence Malick and Woody Allen. Movie fans who love Sean Penn have also been known to enjoy films starring Andrew Dice Clay and Josh Brolin.

list ordered by

1
+ - 87 16
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Mystic River Emmy Rossum, Sean Penn, Kevin Bacon

23 Times Sean Penn Acted Like a Douche The Best Concert Movies Streaming on Hulu

2
+ - 82 17
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Dead Man Walking Sean Penn, Susan Sarandon, Jack Black

3
+ - 71 16
Carlito's Way is listed (or ranked) 3 on the list The Best Sean Penn Movies
Carlito's Way Al Pacino, Sean Penn, Viggo Mortensen

4
+ - 91 30
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Fast Times at Ridgemont High Nicolas Cage, Sean Penn, Jennifer Jason Leigh

5
+ - 73 24
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I Am Sam Michelle Pfeiffer, Sean Penn, Dakota Fanning

6
+ - 61 20
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Milk James Franco, Sean Penn, Josh Brolin

7
+ - 48 12
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The Game Sean Penn, Michael Douglas, Spike Jonze

8
+ - 41 13
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21 Grams Naomi Watts, Sean Penn, Benicio del Toro

9
+ - 56 25
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Bad Boys Sean Penn, Ally Sheedy, Clancy Brown

10
+ - 31 7
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The Weight of Water Elizabeth Hurley, Sean Penn, Josh Lucas

11
+ - 40 16
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At Close Range Sean Penn, Christopher Walken, Kiefer Sutherland

12
+ - 42 18
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Colors Sean Penn, Robert Duvall, Don Cheadle

13
+ - 23 6
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Taps Tom Cruise, Sean Penn, George C. Scott

14
+ - 29 11
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The Interpreter Nicole Kidman, Sean Penn, Catherine Keener

15
+ - 42 22
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The Thin Red Line George Clooney, John Travolta, Sean Penn

The Best R-Rated Musical Drama Movies 7 Mythical Creatures That Were Found in Real Life

16
+ - 21 5
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Sweet and Lowdown Uma Thurman, Sean Penn, Woody Allen

17
+ - 28 13
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The Falcon and the Snowman Sean Penn, Timothy Hutton, Michael Ironside

18
+ - 20 8
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Hurlyburly Meg Ryan, Anna Paquin, Sean Penn

19
+ - 23 11
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State of Grace Sean Penn, Gary Oldman, Robin Wright

20
+ - 18 7
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Up at the Villa Sean Penn, Anne Bancroft, Kristin Scott Thomas

21
+ - 17 7
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The Assassination of Richard Nixon Naomi Watts, Sean Penn, Don Cheadle

22
+ - 17 7
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This Must Be the Place Sean Penn, Frances McDormand, David Byrne

23
+ - 21 12
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Casualties of War Sean Penn, Michael J. Fox, John C. Reilly

24
+ - 13 5
Gangster Squad is listed (or ranked) 24 on the list The Best Sean Penn Movies
Gangster Squad Emma Stone, Sean Penn, Ryan Gosling

25
+ - 19 11
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We're No Angels Demi Moore, Robert De Niro, Sean Penn

26
+ - 14 7
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Racing with the Moon Nicolas Cage, Sean Penn, Crispin Glover

27
+ - 17 10
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All the King's Men Kate Winslet, Sean Penn, Jude Law

28
+ - 11 5
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Before Night Falls Johnny Depp, Sean Penn, Javier Bardem

29
+ - 14 8
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U Turn Jennifer Lopez, Sean Penn, Claire Danes

The Best Eva Mendes Movies How To Annoy Your Bartender

30
+ - 14 9
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Fair Game Naomi Watts, Sean Penn, Ty Burrell

31
+ - 6 2
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Judgment in Berlin Sean Penn, Martin Sheen, Sam Wanamaker

32
+ - 8 5
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It's All About Love Sean Penn, Claire Danes, Joaquin Phoenix

33
+ - 9 7
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What Just Happened Kristen Stewart, Bruce Willis, Robert De Niro

34
+ - 8 6
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Persepolis Sean Penn, Catherine Deneuve, Iggy Pop

35
+ - 8 7
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She's So Lovely John Travolta, Sean Penn, Robin Wright

36
+ - 4 3
Heart Stopper is listed (or ranked) 36 on the list The Best Sean Penn Movies
Heart Stopper Morgan Freeman, Sean Penn, Heather Graham

37
+ - 15 15
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The Tree of Life Brad Pitt, Sean Penn, Jessica Chastain

38
+ - 5 5
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Crackers Sean Penn, Donald Sutherland, Christine Baranski

39
+ - 3 3
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Dear America: Letters Home from Vietnam Robert De Niro, Robin Williams, Sean Penn

40
+ - 3 3
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The Cutting Edge: The Magic of Movie Editing Jodie Foster, Steven Spielberg, Rob Cohen

41
+ - 2 2
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The People Speak Ben Affleck, Matt Damon, Marisa Tomei

42
+ - 2 3
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Phil Ochs: There but for Fortune Sean Penn, Joan Baez, Christopher Hitchens

43
+ - 2 3
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A Constant Forge Peter Falk

The Best Jeff Goldblum Movies The Funniest TV Shows of All Time

44
+ - 4 6
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Love Sean Penn, Robin Wright, William Hurt

45
+ - 2 4
This So-Called Disaster is listed (or ranked) 45 on the list The Best Sean Penn Movies
This So-Called Disaster Sean Penn, Nick Nolte, T Bone Burnett

46
+ - 1 3
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47
+ - 1 3
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Hugo Pool Robert Downey Jr., Alyssa Milano, Sean Penn

48
+ - 1 4
Buy the Ticket, Take the Ride is listed (or ranked) 48 on the list The Best Sean Penn Movies
Buy the Ticket, Take the Ride Bill Murray, Nick Nolte, Gary Busey

49
+ - 1 4
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Cool Blue Sean Penn, Woody Harrelson, Hank Azaria

50
+ - 7 11
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Shanghai Surprise Madonna, Sean Penn, George Harrison