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The Best Sean Penn Movies

Updated November 13, 2019 3.0k votes 529 voters 40.4k views55 items

List RulesVote 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?"

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    Mystic River

    Emmy Rossum, Sean Penn
    Mystic River is a 2003 American mystery drama film directed and scored by Clint Eastwood. It...  more

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    #29 of 230 The Best Psychological Thrillers of All Time#7 of 38 The Best Movies Coming to Netflix in May 2021

  • 2
    72
    13

    Taps

    Tom Cruise, Sean Penn
    Taps is a 1981 drama film starring George C. Scott and Timothy Hutton, with Ronny Cox, Tom...  more

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    #91 of 173 The Most Utterly Depressing Movies Ever Made#289 of 512 The Greatest Movies Of The 1980s, Ranked

  • 3
    71
    15

    The Interpreter

    Nicole Kidman, Sean Penn
    The Interpreter is a 2005 political thriller film starring Nicole Kidman, Sean Penn, and...  more

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    #28 of 154 The Best Political Thriller Movies#30 of 70 The Best Nicole Kidman Movies

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    82
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    Carlito's Way

    Al Pacino, Sean Penn
    Carlito's Way is a 1993 American drama film directed by Brian De Palma, based on the novels...  more

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    #9 of 123 The Best Mafia Films Of All Time#11 of 82 The Best Gangster Movies of the 1990s

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    82
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    Dead Man Walking

    Sean Penn, Susan Sarandon
    This film is a 1995 American drama film starring Susan Sarandon and Sean Penn, and co-produced...  more

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    #452 of 1,195 Every Oscar Winning Film Ever#157 of 440 Your Favorite Movies of the 1990s

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    91
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    Fast Times at Ridgemont High

    Nicolas Cage, Sean Penn
    Fast Times at Ridgemont High is a 1982 American coming-of-age teen comedy film written by...  more

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    #262 of 1,506 The Most Rewatchable Movies#23 of 306 The Best Ensemble Movies

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    75
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    The Weight of Water

    Elizabeth Hurley, Sean Penn
    The Weight of Water is a 2000 French-American mystery thriller film based on Anita Shreve's...  more
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    61
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    The Game

    Sean Penn, Michael Douglas
    The Game is a 1997 American mystery thriller film directed by David Fincher, starring Michael...  more

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    #15 of 24 The Best Movies with Twist Endings#36 of 162 The Best and Scariest Psychological Thrillers of All Time

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    73
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    Bad Boys

    Sean Penn, Ally Sheedy
    Bad Boys is a 1983 drama film written by Richard Di Lello and directed by Rick Rosenthal....  more
  • 10
    46
    13

    All the King's Men

    Kate Winslet, Sean Penn
    All the King's Men is a 2006 film adaptation of the 1946 Pulitzer Prize-winning novel All the...  more
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    66
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    Milk

    James Franco, Sean Penn
    Milk is a 2008 American biographical film based on the life of gay rights activist and...  more

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    #95 of 301 The Best Movies Based On True Stories#179 of 675 The Best Movies Roger Ebert Gave Four Stars

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    73
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    I Am Sam

    Sean Penn, Dakota Fanning
    I Am Sam is a 2001 American drama film directed by Jessie Nelson. A mentally handicapped man...  more

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    #63 of 277 The Top Tearjerker Movies That Make Men Cry#128 of 291 The Greatest Soundtracks of All Time

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    50
    20

    21 Grams

    Naomi Watts, Sean Penn
    21 Grams is a 2003 American drama film directed by Mexican director Alejandro González...  more

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    #18 of 32 30+ Great Movies About Depression in Women#74 of 157 The Best Movies About Tragedies

  • 14
    55
    26

    Hurlyburly

    Meg Ryan, Anna Paquin
    Hurlyburly is a 1998 independent film, based on the acclaimed 1984 play of the same name by...  more
  • 15
    49
    23

    Colors

    Sean Penn, Robert Duvall
    Colors is a 1988 American police procedural action film starring Sean Penn and Robert Duvall,...  more

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    #32 of 85 The Best Movies About Corrupt Cops#25 of 132 The Best Films Directed by Famous Actors

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    46
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    At Close Range

    Sean Penn, Christopher Walken
    At Close Range is a 1986 crime drama film directed by James Foley, based on the real life...  more
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    43
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    Up at the Villa

    Sean Penn, Anne Bancroft
    Up at the Villa is a 2000 drama film written by W. Somerset Maugham and directed by Philip...  more
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    29
    15

    Before Night Falls

    Johnny Depp, Sean Penn
    Before Night Falls is a 2000 American drama film directed by Julian Schnabel. The screenplay...  more

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    #56 of 106 The Best Movies About Writers#24 of 31 31 Movie Trailers That Made You Weep

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    Judgment in Berlin

    Sean Penn, Martin Sheen
    Judgment in Berlin is a 1988 drama film written by Herbert J. Stern, Joshua Sinclair and Leo...  more
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    36
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    Fair Game

    Naomi Watts, Sean Penn
    Fair Game is a 2010 biographical spy drama film directed by Doug Liman and starring Naomi...  more

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    #46 of 90 The Greatest Movies About CIA Agents & Operatives#219 of 340 The Best Political Films Ever Made

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    21
    13

    This Must Be the Place

    Sean Penn, Frances McDormand
    This Must Be the Place is a 2011 European drama film directed by Paolo Sorrentino, written by...  more
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    17
    12

    Crackers

    Sean Penn, Donald Sutherland
    Crackers is a 1984 American film directed by Louis Malle. It was entered into the 34th Berlin...  more
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    What Just Happened

    Kristen Stewart, Bruce Willis
    What Just Happened is a satirical comedy-drama directed by Barry Levinson and starring Robert...  more
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    13
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    The Cutting Edge: The Magic of Movie Editing

    Jodie Foster, Steven Spielberg
    The Cutting Edge: The Magic of Movie Editing is a 2004 documentary film directed by filmmaker...  more
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    It's All About Love

    Sean Penn, Claire Danes
    It's All About Love is a 2003 romance-drama film written and directed by Thomas Vinterberg....  more