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Over 10,000 of The Top Box Office Movie Hits... Over the Last 75 Years...

Sean Penn's Best Movies

Sean

Sean Penn's Portrait

Penn

Sean Penn has made 8 movies in which he starred in a leading role since his first movie 23 years ago called "U-Turn" (1997) in which he portrayed the character Bobby Cooper.

The highest grossing movie of Sean Penn's career, "Mystic River", sold nearly $90,135,191 at the box office in 2003.

Ranked #45 of All Actors
Sean Penn's Movies

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PopularityYear
Mystic River Poster

Mystic River

Movie Genre: Drama

Running Time: 137 minutes

Starring:

Sean

Sean Penn's Portrait

Penn

Plays as

Jimmy Markum

(Leading Role)

Tim

Tim Robbins's Portrait

Robbins

Plays as

Dave Boyle

(Leading Role)

Kevin

Kevin Bacon's Portrait

Bacon

Plays as

Sean Devine

(Leading Role)

Laurence

Laurence Fishburne's Portrait

Fishburne

Plays as

Whitey Powers

(Supporting Role)

Directed by: Clint Eastwood

Sean Penn's Character Name: Jimmy Markum

Box Office Sales: $90,135,191

Rated: Rated R For language and violence.

Year
Released 2003
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The Interpreter Poster

The Interpreter

Movie Genre: Thriller/Suspense

Running Time: 128 minutes

Starring:

Nicole

Nicole Kidman's Portrait

Kidman

Plays as

Silvia Broome

(Leading Role)

Sean

Sean Penn's Portrait

Penn

Plays as

Tobin Keller

(Leading Role)

Catherine

Catherine Keener's Portrait

Keener

Plays as

Dot Woods

(Supporting Role)

Jesper

Jesper Christensen's Portrait

Christensen

Plays as

Nils Lud

(Supporting Role)

Directed by: Sydney Pollack

Sean Penn's Character Name: Tobin Keller

Box Office Sales: $72,708,161

Rated: Rated PG-13 For violence, some sexual content and brief strong language.

Year
Released 2005
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Milk Poster

Milk

Movie Genre: Drama

Running Time: 128 minutes

Starring:

Sean

Sean Penn's Portrait

Penn

Plays as

Harvey Milk

(Leading Role)

Emile

Emile Hirsch's Portrait

Hirsch

Plays as

Cleve Jones

(Supporting Role)

Josh

Josh Brolin's Portrait

Brolin

Plays as

Dan White

(Supporting Role)

Diego

Diego Luna's Portrait

Luna

Plays as

Jack Lira

(Supporting Role)

Directed by: Gus Van Sant

Sean Penn's Character Name: Harvey Milk

Box Office Sales: $31,841,299

Rated: Rated R For language, some sexual content and brief violence.

Year
Released 2008
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The Tree of Life Poster

The Tree of Life

Movie Genre: Drama

Running Time: 138 minutes

Starring:

Brad

Brad Pitt's Portrait

Pitt

Plays as

Mr. O'Brien

(Leading Role)

Sean

Sean Penn's Portrait

Penn

Plays as

Jack

(Leading Role)

Jessica

Jessica Chastain's Portrait

Chastain

Plays as

Mrs. O'Brien

(Leading Role)

Fiona

Fiona Shaw's Portrait

Shaw

Plays as

Grandmother

(Supporting Role)

Directed by: Terrence Malick

Sean Penn's Character Name: Jack

Box Office Sales: $13,305,665

Rated: Rated PG-13 For some thematic material.

Synopsis: The impressionistic story of a Midwestern family in the 1950's. The film follows the life journey of the eldest son, Jack, through the innocence of childhood to his disillusioned adult years as he tries to reconcile a complicated relationship with his father. Jack finds himself a lost soul in the modern world, seeking answers to the origins and meaning of life while questioning the existence of faith. Through Malick's signature imagery, we see how both brute nature and spiritual grace shape not only our lives as individuals and families, but all life.

Year
Released 2010
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Fair*Game Poster

Fair*Game

Movie Genre: Drama

Running Time: 105 minutes

Starring:

Naomi

Naomi Watts's Portrait

Watts

Plays as

Valerie Plame

(Leading Role)

Sean

Sean Penn's Portrait

Penn

Plays as

Joseph Wilson

(Leading Role)

Sam

Sam Shepard's Portrait

Shepard

Plays as

Sam Plame

(Supporting Role)

Noah

Noah Emmerich's Portrait

Emmerich

Plays as

Bill

(Supporting Role)

Directed by: Doug Liman

Sean Penn's Character Name: Joseph Wilson

Box Office Sales: $9,540,691

Rated: Rated PG-13 For some language.

Synopsis: Fair Game is a drama inspired by the experiences of real-life undercover CIA officer Valarie Plame, whose career is destroyed and her marriage strained to its limits when her covert status is exposed by a White House press leak. As a covert officer in the CIA's Counter-Proliferation Division, Valerie leads an investigation into the existence of weapons of mass destruction in Iraq. Valarie's husband, diplomat Joe Wilson, is drawn into the investigation to substantiate an alleged sale of enriched uranium from Niger. But when the Administration ignores his findings and uses the issue to support the call to war, Joe writes a New York Times editorial outlining his conclusions and ignites a firestorm of controversy.

Year
Released 2010
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All the King's Men Poster

All the King's Men

Movie Genre: Drama

Starring:

Sean

Sean Penn's Portrait

Penn

Plays as

Willie Stark

(Leading Role)

Jude

Jude Law's Portrait

Law

Plays as

Jack Burden

(Leading Role)

Anthony

Anthony Hopkins's Portrait

Hopkins

Plays as

Judge Irwin

(Supporting Role)

Kate

Kate Winslet's Portrait

Winslet

Plays as

Anne Stanton

(Supporting Role)

Directed by: Steven Zaillian

Sean Penn's Character Name: Willie Stark

Box Office Sales: $7,221,458

Rated: Rated PG-13 For an intense sequence of violence, sexual content and partial nudity.

Year
Released 2006
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U-Turn Poster

U-Turn

Movie Genre: Drama

Starring:

Claire

Claire Danes's Portrait

Danes

Plays as

Jenny

(Supporting Role)

Jon

Jon Voight's Portrait

Voight

Plays as

Blind Man

(Supporting Role)

Billy Bob

Billy Bob Thornton's Portrait

Thornton

Plays as

Darrell

(Supporting Role)

Nick

Nick Nolte's Portrait

Nolte

Plays as

Jake McKenna

(Leading Role)

Jennifer

Jennifer Lopez's Portrait

Lopez

Plays as

Grace McKenna

(Leading Role)

Joaquin

Joaquin Phoenix's Portrait

Phoenix

Plays as

Toby N. Tucker

(Supporting Role)

Liv

Liv Tyler's Portrait

Tyler

Plays as

Girl in Bus Station

(Supporting Role)

Sean

Sean Penn's Portrait

Penn

Plays as

Bobby Cooper

(Leading Role)

Directed by: Oliver Stone

Sean Penn's Character Name: Bobby Cooper

Box Office Sales: $6,690,074

Rated: Rated R For strong violence, sexuality and language.

Year
Released 1997
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This Must Be the Place Poster

This Must Be the Place

Movie Genre: Black Comedy

Running Time: 118 minutes

Starring:

Sean

Sean Penn's Portrait

Penn

Plays as

Cheyenne

(Leading Role)

Frances

Frances McDormand's Portrait

McDormand

Plays as

Jane

(Supporting Role)

Judd

Judd Hirsch's Portrait

Hirsch

Plays as

Mordecai Midler

(Supporting Role)

Harry Dean

Harry Dean Stanton's Portrait

Stanton

Plays as

Robert Plath

(Supporting Role)

Directed by: Paolo Sorrentino

Sean Penn's Character Name: Cheyenne

Box Office Sales: $142,242

Rated: Rated R For language, some sexual content and brief disturbing images.

Synopsis: Cheyenne is a former rock star. At 50, he still dresses 'Goth' and lives in Dublin off his royalties. The death of his father, with whom he wasn't on speaking terms, brings him back to New York. He discovers his father had an obsession: to seek revenge for a humiliation he had suffered. Cheyenne decides to pick up where his father left off, and starts a journey, at his own pace, across America.

Year
Released 2010
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