Entertainment

The Best Sean Penn Movies

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?"
Ranked by
  • Mystic River
    1
    Sean Penn, Tim Robbins, Kevin Bacon
    • Released: 2003
    • Directed by: Clint Eastwood
  • Fast Times at Ridgemont High
    2
    Sean Penn, Jennifer Jason Leigh, Judge Reinhold
    • Released: 1982
    • Directed by: Amy Heckerling
  • Carlito's Way
    3
    Al Pacino, Sean Penn, Penelope Ann Miller
    • Released: 1993
    • Directed by: Brian De Palma
  • Dead Man Walking
    4
    Susan Sarandon, Sean Penn, Robert Prosky
    • Released: 1995
    • Directed by: Tim Robbins
  • Bad Boys
    5
    Sean Penn, Reni Santoni, Esai Morales
    • Released: 1983
    • Directed by: Rick Rosenthal
  • The Game
    6
    Sean Penn, Michael Douglas, Spike Jonze
    • Released: 1997
    • Directed by: David Fincher, Pedro Coutinho
  • I Am Sam
    7
    Sean Penn, Michelle Pfeiffer, Dakota Fanning
    • Released: 2001
    • Directed by: Jessie Nelson
  • Colors
    8
    Sean Penn, Robert Duvall, Maria Conchita Alonso
    • Released: 1988
    • Directed by: Dennis Hopper
  • 21 Grams
    9
    Sean Penn, Benicio Del Toro, Naomi Watts
    • Released: 2003
    • Directed by: Alejandro González Iñárritu
  • The Thin Red Line
    10
    Sean Penn, Adrien Brody, Jim Caviezel
    • Released: 1998
    • Directed by: Terrence Malick
  • At Close Range
    11
    Sean Penn, Christopher Walken, Mary Stuart Masterson
    • Released: 1986
    • Directed by: James Foley
  • Milk
    12
    Sean Penn, Emile Hirsch, Josh Brolin
    • Released: 2008
    • Directed by: Gus Van Sant
  • The Falcon and the Snowman
    13
    Timothy Hutton, Sean Penn, David Suchet
    • Released: 1985
    • Directed by: John Schlesinger
  • State of Grace
    14
    Sean Penn, Ed Harris, Gary Oldman
    • Released: 1990
    • Directed by: Phil Joanou
  • Casualties of War
    15
    Michael J. Fox, Sean Penn, Don Harvey
    • Released: 1989
    • Directed by: Brian De Palma
  • Racing with the Moon
    16
    Sean Penn, Elizabeth McGovern, Nicolas Cage
    • Released: 1984
    • Directed by: Richard Benjamin
  • Taps
    17
    Timothy Hutton, George C. Scott, Ronny Cox
    • Released: 1981
    • Directed by: Harold Becker
  • This Must Be the Place
    18
    Sean Penn, Frances McDormand, David Byrne
    • Released: 2011
    • Directed by: Paolo Sorrentino
  • The Professor and the Madman
    19
    Mel Gibson, Sean Penn, Natalie Dormer
    • Released: 2019
    • Directed by: P.B. Shemran
  • Sweet and Lowdown
    20
    Sean Penn, Samantha Morton, Uma Thurman
    • Released: 1999
    • Directed by: Woody Allen
  • U Turn
    21
    Jennifer Lopez, Sean Penn, Claire Danes
    • Released: 1997
    • Directed by: Oliver Stone
  • The Weight of Water
    22
    Catherine McCormack, Sarah Polley, Sean Penn
    • Released: 2000
    • Directed by: Kathryn Bigelow
  • The Tree of Life
    23
    Brad Pitt, Sean Penn, Jessica Chastain
    • Released: 2011
    • Directed by: Terrence Malick
  • We're No Angels
    24
    Robert De Niro, Sean Penn, Demi Moore
    • Released: 1989
    • Directed by: Neil Jordan
  • Gangster Squad
    25
    Josh Brolin, Ryan Gosling, Nick Nolte
    • Released: 2013
    • Directed by: Ruben Fleischer