Entertainment
532 voters

The Best Sean Penn Movies

Updated November 13, 2019 3.1k votes 532 voters 40.5k 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?"

list.itemsDescription

...more
  • 26
    21
    22

    Racing with the Moon

    Nicolas Cage, Sean Penn

    Released1984

    Directed byRichard Benjamin

    Racing with the Moon is a 1984 American drama film starring Sean Penn, Elizabeth McGovern, and Nicolas Cage. It was directed by Richard Benjamin and written by Steven Kloves. The original music score...  more

    More Racing with the Moon 

    #71 of 98 The Best Nicolas Cage Movies#15 of 23 The Best Bowling Movies

  • 27
    5
    0

    The Professor and the Madman

    Mel Gibson, Sean Penn

    Released2019

    Directed byP.B. Shemran

    The Professor and the Madman is a 2019 biographical drama film direted by P.B. Sherman, based on the 1998 book The Surgeon of Crowthorne by Simon Winchester. In 1857, a professor begins compiling the...  more
  • 28
    11
    9

    Released2010

    Directed byKenneth Bowser

    Phil Ochs: There but for Fortune is a documentary film on the life and times of folk singer-songwriter Phil Ochs. The film, released theatrically in January 2011, was written and directed by Kenneth...  more
  • 29
    46
    57

    At Close Range

    Sean Penn, Christopher Walken

    Released1986

    Directed byJames Foley

    At Close Range is a 1986 crime drama film directed by James Foley, based on the real life rural Pennsylvania crime family led by Bruce Johnston, Sr. which operated during the 1960s and 1970s. It...  more
  • 30
    22
    25

    She's So Lovely

    John Travolta, Sean Penn

    Released1997

    Directed byNick Cassavetes

    She's So Lovely is a 1997 film directed by Nick Cassavetes, written by John Cassavetes. At the time of its release, it received special attention because, eight years after his death, it was the...  more
  • 31
    28
    33

    State of Grace

    Sean Penn, Gary Oldman

    Released1990

    Directed byPhil Joanou

    State of Grace is a 1990 neo-noir film starring Sean Penn, Ed Harris and Gary Oldman, also featuring Robin Wright, John Turturro and John C. Reilly. Written by Dennis McIntyre and directed by Phil...  more

    More State of Grace 

    #45 of 128 The Best Mafia Films Of All Time#24 of 82 The Best Gangster Movies Of The 1990s

  • 32
    43
    57

    The Thin Red Line

    George Clooney, John Travolta

    Released1998

    Directed byTerrence Malick

    The Thin Red Line is a 1998 American ensemble epic film written and directed by Terrence Malick. Based on the novel by James Jones, it tells a fictionalized version of the Battle of Mount Austen,...  more

    More The Thin Red Line 

    #154 of 440 The Best Movies Of The 1990s#28 of 55 The Best Memorial Day Movies

  • 33
    21
    26

    Sweet and Lowdown

    Uma Thurman, Sean Penn

    Released1999

    Directed byWoody Allen

    Sweet and Lowdown is a 1999 American comedy-drama film written and directed by Woody Allen. The film tells the story, set in the 1930s, of a fictional jazz guitarist named Emmet Ray who regards...  more
  • 34
    30
    40

    The Falcon and the Snowman

    Sean Penn, Timothy Hutton

    Released1985

    Directed byJohn Schlesinger

    The Falcon and the Snowman is a 1985 spy film directed by John Schlesinger about two young American men, Christopher Boyce and Daulton Lee, who sold U.S. security secrets to the Soviet Union. The...  more

    More The Falcon and the Snowman 

    #59 of 90 The Greatest Movies About CIA Agents & Operatives#61 of 334 The Best Political Films Ever Made

  • 35
    9
    9

    Dear America: Letters Home from Vietnam

    Robert De Niro, Robin Williams

    Released1987

    Directed byBill Couturié

    Dear America: Letters Home from Vietnam is an American grammy Award–winning 1987 documentary, inspired by the anthology of the same title, directed by Bill Couturié. Using real letters written by US...  more

    More Dear America: Letters Home from Vietnam 

    #99 of 389 The Greatest Documentaries of All Time#10 of 51 The Best Documentaries About Vietnam

  • 36
    28
    38

    Casualties of War

    Sean Penn, Michael J. Fox

    Released1989

    Directed byBrian De Palma

    This film is a 1989 drama film directed by Brian De Palma, with a screenplay by David Rabe, based on the actual events of the incident on Hill 192 in 1966 during Vietnam. It stars Michael J. Fox and...  more

    More Casualties of War 

    #193 of 376 The 50+ Best War Movies Ever Made, Ranked#440 of 512 The Greatest Movies Of The 1980s, Ranked

  • 37
    11
    14

    This So-Called Disaster

    Sean Penn, Nick Nolte

    Released2003

    Directed byMichael Almereyda

    This So-Called Disaster is a 2003 documentary film directed by Michael Almereyda....
  • 38
    9
    11

    Buy the Ticket, Take the Ride

    Bill Murray, Nick Nolte

    Released2006

    Directed byTom Thurman

    Buy the Ticket, Take the Ride is a 2006 documentary film written by Tom Marksbury and directed by Tom Thurman....  more
  • 39
    19
    28

    U Turn

    Jennifer Lopez, Sean Penn

    Released1997

    Directed byOliver Stone

    U Turn is a 1997 American neo-noir crime thriller film directed by Oliver Stone and starring Sean Penn, Billy Bob Thornton, Jennifer Lopez, Jon Voight, Powers Boothe, Joaquin Phoenix, Claire Danes,...  more
  • 40
    10
    16

    Heart Stopper

    Morgan Freeman, Sean Penn

    Released2014

    Directed byPaul Flaherty

    Heart Stopper is a 2012 thriller film written by Michael Z. Gordon and directed by Paul Flaherty....
  • 41
    7
    12

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

    Sean Penn

    Released2007

    Directed byJeremy Earp, Loretta Alper

    Narrated by Sean Penn and based on the work of media critic and best- selling author Norman Solomon, who traveled with Penn to Baghdad just before the war to call attention to the dangers of a U.S....  more
  • 42
  • 43
    7
    13

    Cool Blue

    Sean Penn, Woody Harrelson

    Released1990

    Directed byRichard Shepard, Mark Mullin

    Cool Blue is a 1990 English language romantic comedy starring Woody Harrelson, Ely Pouget, and Hank Azaria and directed by Mark Mullin and Richard Shepard. The film received an R rating by the MPAA....  more
  • 44
    6
    13

    The People Speak

    Ben Affleck, Matt Damon

    Released2008

    Directed byHoward Zinn, Chris Moore, Anthony Arnove

    The People Speak is a documentary tv program/film....  more
  • 45
    20
    35

    The Tree of Life

    Brad Pitt, Sean Penn

    Released2011

    Directed byTerrence Malick

    The Tree of Life is a 2011 American experimental drama film written and directed by Terrence Malick and starring Brad Pitt, Sean Penn, and Jessica Chastain. The film chronicles the origins and...  more

    More The Tree of Life 

    #371 of 675 The Best Movies Roger Ebert Gave Four Stars#427 of 549 The Greatest Epic Movies Ever Made

  • 46
    15
    27

    Released2004

    Directed byNiels Mueller

    This film is a 2004 American film, directed by Niels Mueller. It stars Sean Penn, Don Cheadle and Naomi Watts, and is based on the story of Samuel Byck, who plotted against Richard Nixon in 1974. It...  more
  • 47
    18
    34

    Shanghai Surprise

    Madonna, Sean Penn

    Released1986

    Directed byJim Goddard

    Shanghai Surprise is a 1986 British adventure comedy film starring then-newlyweds Sean Penn and Madonna, produced by George Harrison's HandMade Films and distributed by Metro-Goldwyn-Mayer. Harrison...  more

    More Shanghai Surprise 

    #45 of 327 The Best Free Movies On YouTube, Ranked#12 of 25 The Most Infamous Box Office Flop From The Year You Were Born

  • 48
    6
    15

    A Constant Forge

    Peter Falk

    Released2000

    Directed byCharles Kiselyak

    A Constant Forge is a 2000 documentary film directed by Charles Kiselyak about the life and work of John Cassavetes. It contains interviews with Cassavetes himself as well as recollections by actors...  more
  • 49
    7
    16

    Deflating the Elephant

    Sean Penn

    Released2008

    Directed byAldo Vidali

  • 50
    17
    34

    We're No Angels

    Demi Moore, Robert De Niro

    Released1989

    Directed byNeil Jordan

    We're No Angels is a 1989 comedy film directed by Neil Jordan. It stars Robert De Niro, Sean Penn, and Demi Moore. This was Jordan's last film to receive a PG-13 rating by the MPAA, until Ondine in...  more

    More We're No Angels 

    #227 of 305 The Funniest '80s Movies#23 of 26 The Best Brat Pack Movies