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
94 17
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Mystic River Emmy Rossum, Sean Penn, Kevin Bacon

Sean Penn Has Always Been Hollywood's Biggest Psycho The Best Netflix Original Stand-Up Comedy Specials

2
92 19
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Dead Man Walking Sean Penn, Susan Sarandon, Jack Black

3
76 17
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
97 31
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Fast Times at Ridgemont High Nicolas Cage, Sean Penn, Jennifer Jason Leigh

5
81 24
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I Am Sam Michelle Pfeiffer, Sean Penn, Dakota Fanning

6
53 13
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The Game Sean Penn, Michael Douglas, Spike Jonze

7
65 21
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Milk James Franco, Sean Penn, Josh Brolin

8
63 27
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Bad Boys Sean Penn, Ally Sheedy, Clancy Brown

9
43 14
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21 Grams Naomi Watts, Sean Penn, Benicio del Toro

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

11
44 17
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At Close Range Sean Penn, Christopher Walken, Kiefer Sutherland

12
43 18
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Colors Sean Penn, Robert Duvall, Don Cheadle

13
24 6
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Taps Tom Cruise, Sean Penn, George C. Scott

14
43 22
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The Thin Red Line George Clooney, John Travolta, Sean Penn

15
22 5
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Sweet and Lowdown Uma Thurman, Sean Penn, Woody Allen

The Worst A-List Hollywood Actors Mythical Creatures That Were Found in Real Life

16
29 11
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The Interpreter Nicole Kidman, Sean Penn, Catherine Keener

17
29 13
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The Falcon and the Snowman Sean Penn, Timothy Hutton, Michael Ironside

18
24 11
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State of Grace Sean Penn, Gary Oldman, Robin Wright

19
20 8
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Hurlyburly Meg Ryan, Anna Paquin, Sean Penn

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

21
18 8
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This Must Be the Place Sean Penn, Frances McDormand, David Byrne

22
14 5
Gangster Squad is listed (or ranked) 22 on the list The Best Sean Penn Movies
Gangster Squad Emma Stone, Sean Penn, Ryan Gosling

23
17 8
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The Assassination of Richard Nixon Naomi Watts, Sean Penn, Don Cheadle

24
20 11
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We're No Angels Demi Moore, Robert De Niro, Sean Penn

25
15 7
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Racing with the Moon Nicolas Cage, Sean Penn, Crispin Glover

26
18 10
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All the King's Men Kate Winslet, Sean Penn, Jude Law

27
22 14
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Casualties of War Sean Penn, Michael J. Fox, John C. Reilly

28
15 8
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U Turn Jennifer Lopez, Sean Penn, Claire Danes

29
11 5
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Before Night Falls Johnny Depp, Sean Penn, Javier Bardem

The Best Teen Romance Movies 25 Things You Should Probably Stop Blaming on Millennials

30
14 10
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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
9 8
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She's So Lovely John Travolta, Sean Penn, Robin Wright

35
8 7
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Persepolis Sean Penn, Catherine Deneuve, Iggy Pop

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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Hugo Pool Robert Downey Jr., Alyssa Milano, Sean Penn

Sean Penn's Loves & Hookups The Best Reality TV Shows Since 2015

44
2 3
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A Constant Forge Peter Falk

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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War Made Easy: How Presidents & Pundits Keep Spinning Us to Death Sean Penn

47
1 4
Buy the Ticket, Take the Ride is listed (or ranked) 47 on the list The Best Sean Penn Movies
Buy the Ticket, Take the Ride Bill Murray, Nick Nolte, Gary Busey

48
1 4
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Cool Blue Sean Penn, Woody Harrelson, Hank Azaria

49
4 8
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Love Sean Penn, Robin Wright, William Hurt

50
3 7
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Pauly Shore Is Dead Britney Spears, Paris Hilton, Pamela Anderson