All Of Sean Penn's Movies, Ranked

Ranker Film
Updated September 15, 2023 2.8K votes 583 voters 41.7K views
Over 500 Ranker voters have come together to rank this list of All Of Sean Penn's Movies, Ranked
Voting Rules
Vote for your favorite Sean Penn movies, regardless of critic reviews or how big the role was.

With more than 500 movie fans casting votes, this list of the best Sean Penn movies is a great way to explore the work of one of Hollywood's most accomplished actors. During his decades-long career, Sean Penn has consistently captivated audiences with his intense and powerful performances in some of the greatest films ever made.

From memorable roles like Jeff Spicoli in Fast Times at Ridgemont High or David Kleinfeld in Carlito's Way to critically acclaimed turns as Danny McGavin in Colors and Sam Dawson in I Am Sam, Penn has demonstrated an incredible range that few other actors can match. By exploring these emotional depths, he breathes life into characters who are deeply flawed but still capable of love and redemption.

Penn's commitment to realism also comes through vividly on screen; each performance is imbued with an authenticity that only further enhances both character arcs and overall story development. So if you're looking for an unforgettable cinema experience, check out this list for what could be your favorite Sean Penn film yet. Don't forget to vote up your favorites.

Most divisive: She's So Lovely
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  • Mystic River
    1

    Mystic River

    Sean Penn, Tim Robbins, Kevin Bacon
    127 votes
    • Released: 2003
    • Directed by: Clint Eastwood
    In Mystic River, childhood friends Jimmy Markum (Sean Penn), Dave Boyle (Tim Robbins), and Sean Devine (Kevin Bacon) are drawn back together after a horrifying incident shakes their Boston neighborhood. Directed by Clint Eastwood, this gripping drama examines the lasting impact of trauma on friendship and family. It's a tale woven with threads of suspicion, grief, and loss - all underpinned by an unyielding quest for justice. The film won two Academy Awards: Best Actor for Penn and Best Supporting Actor for Robbins. A complex narrative unfolds against the gritty backdrop of working-class Boston, where past demons refuse to rest.

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  • Fast Times at Ridgemont High
    2

    Fast Times at Ridgemont High

    Sean Penn, Jennifer Jason Leigh, Judge Reinhold
    129 votes
    • Released: 1982
    • Directed by: Amy Heckerling
    In the iconic 80s coming-of-age film, Fast Times at Ridgemont High, teenage life is under the microscope. Amidst Southern California's sun-soaked malls and high schools, we follow a group of students as they navigate adolescent adventures. Our key characters include Stacy Hamilton (Jennifer Jason Leigh), a young girl grappling with her burgeoning sexuality, her best friend Linda Barrett (Phoebe Cates), Mark Ratner (Brian Backer) the shy novice in love, and Jeff Spicoli (Sean Penn), the perennial surfer dude. Directed by Amy Heckerling, this movie weaves together tales of love, loss, and teen angst against a backdrop of carefree adolescence and rock 'n' roll.

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  • Dead Man Walking
    3

    Dead Man Walking

    Susan Sarandon, Sean Penn, Robert Prosky
    107 votes
    • Released: 1995
    • Directed by: Tim Robbins
    As death row inmate Matthew Poncelet (Sean Penn) nears his execution date, he calls upon Sister Helen Prejean (Susan Sarandon) to help him with one last appeal, maintaining that he is innocent of the murders of a young couple. Poncelet begins to form a bond with Prejean, and she visits both his family and the relatives of the victims, hoping to learn more about the case. As things begin to look bleak for Poncelet, Prejean does all that she can to comfort and console the hardened convict.

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  • Carlito's Way
    4

    Carlito's Way

    Al Pacino, Sean Penn, Penelope Ann Miller
    102 votes
    • Released: 1993
    • Directed by: Brian De Palma
    A free man after years in prison, Carlito Brigante (Al Pacino) intends to give up his criminal ways, but it's not long before the ex-con is sucked back into the New York City underworld. Reconnecting with his dancer girlfriend, Gail (Penelope Ann Miller), Carlito gets entangled in the shady dealings of his friend Dave Kleinfeld (Sean Penn), who also serves as his lawyer. When Carlito and Kleinfeld run afoul of shifty gangster Benny Blanco (John Alberto Leguizamo), it sets them on a dangerous path.

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  • I Am Sam
    5

    I Am Sam

    Sean Penn, Michelle Pfeiffer, Dakota Fanning
    101 votes
    • Released: 2001
    • Directed by: Jessie Nelson
    I Am Sam is a heartfelt drama that centers around Sam Dawson (Sean Penn), a man with an intellectual disability, who fathers a daughter named Lucy Diamond Dawson (Dakota Fanning). As Lucy grows older, her mental capacity surpasses Sam's, leading to the state deeming him unfit as a parent. The story unfolds as Sam, aided by lawyer Rita Harrison (Michelle Pfeiffer), fights for custody of his daughter. Directed by Jessie Nelson, this film garnered Penn an Academy Award nomination for Best Actor. Notable for its exploration of love and family in unconventional circumstances, I Am Sam challenges societal norms and perceptions.

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  • Bad Boys
    6

    Bad Boys

    Sean Penn, Reni Santoni, Esai Morales
    93 votes
    • Released: 1983
    • Directed by: Rick Rosenthal
    Teen delinquent Mick O'Brien (Sean Penn) is sent to juvenile hall after unintentionally killing the younger sibling of a rival gang leader, Paco Moreno (Esai Morales), in a drug-deal con gone wrong. Prison life proves even more brutal than the streets when Mick is forced to face off against reigning prison toughs Viking (Clancy Brown) and Tweety (Robert Lee Rush). Worse yet, on the outside, Paco is threatening to take revenge on those close to Mick -- including his girlfriend (Ally Sheedy).

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