Year |
Title |
Role |
Director |
Notes |
1981 |
Taps |
Cadet Capt. Alex Dwyer |
Harold Becker |
|
1982 |
Fast Times at Ridgemont High |
Jeff Spicoli |
Amy Heckerling |
|
1982 |
Bad Boys |
Michael O'Brien |
Rick Rosenthal |
|
1983 |
Risky Business |
Unknown |
Paul Brickman |
Uncredited cameo |
1983 |
Summerspell |
Buddy |
|
|
1984 |
Crackers |
Dillard |
Louis Malle |
|
1984 |
Racing with the Moon |
Henry "Hopper" Nash |
Richard Benjamin |
|
1985 |
Falcon and the Snowman, TheThe Falcon and the Snowman |
Daulton Lee |
John Schlesinger |
|
1986 |
At Close Range |
Brad Whitewood Jr. |
James Foley |
|
1986 |
Shanghai Surprise |
Glendon Wasey |
Jim Goddard |
Nominated—Golden Raspberry Award for Worst Actor |
1987 |
Dear America: Letters Home from Vietnam |
Narrator |
Bill Couturié |
Documentary |
1988 |
Cool Blue |
Phil the Plumber |
Mark Mullin & Richard Shepard |
Uncredited[1] |
1988 |
Colors |
Officer Danny McGavin |
Dennis Hopper |
|
1988 |
Judgment in Berlin |
Guenther X |
Leo Penn |
|
1989 |
Casualties of War |
Sgt. Tony Meserve |
Brian De Palma |
|
1989 |
We're No Angels |
Jim |
Neil Jordan |
|
1990 |
State of Grace |
Terry Noonan |
Phil Joanou |
|
1991 |
Schneeweißrosenrot |
Himself |
|
Documentary |
1991 |
The Beaver Trilogy |
"Groovin' Larry" Huff |
Trent Harris |
|
1991 |
Indian Runner, TheThe Indian Runner |
— |
Sean Penn |
Writer, director Nominated—Locarno International Film Festival Golden Leopard |
1992 |
Cruise Control |
Jeffrey |
|
Short film |
1993 |
Last Party, TheThe Last Party |
Himself |
Mark Benjamin & Marc Levin |
Documentary |
1993 |
Carlito's Way |
David Kleinfeld |
Brian De Palma |
Nominated—Chicago Film Critics Association Award for Best Supporting Actor Nominated—Golden Globe Award for Best Supporting Actor – Motion Picture |
1995 |
Crossing Guard, TheThe Crossing Guard |
— |
Sean Penn |
Writer, director Nominated—Golden Lion |
1995 |
Dead Man Walking |
Matthew Poncelet |
Tim Robbins |
Independent Spirit Award for Best Male Lead National Society of Film Critics Award for Best Actor (2nd place) Silver Bear for Best Actor[2] Sant Jordi Award for Best Foreign Actor Nominated—Academy Award for Best Actor Nominated—Chicago Film Critics Association Award for Best Actor Nominated—Golden Globe Award for Best Actor – Motion Picture Drama Nominated—Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role |
1997 |
Loved |
Michael |
Erin Dignam |
|
1997 |
She's So Lovely |
Eddie Quinn |
Nick Cassavetes |
Cannes Film Festival Award for Best Actor[3] |
1997 |
U Turn |
Bobby Cooper |
Oliver Stone |
|
1997 |
Game, TheThe Game |
Conrad Van Orton |
David Fincher |
|
1997 |
Hugo Pool |
Strange Hitchhiker |
Robert Downey, Sr. |
|
1998 |
Hurlyburly |
Eddie |
Anthony Drazan |
Volpi Cup Nominated—Independent Spirit Award for Best Male Lead |
1998 |
Thin Red Line, TheThe Thin Red Line |
1st Sgt. Welsh |
Terrence Malick |
|
1999 |
Being John Malkovich |
Himself |
Spike Jonze |
Uncredited |
1999 |
Sweet and Lowdown |
Emmet Ray |
Woody Allen |
Nominated—Academy Award for Best Actor Nominated—Golden Globe Award for Best Actor – Motion Picture Musical or Comedy Nominated—Satellite Award for Best Actor - Motion Picture Musical or Comedy |
2000 |
Constant Forge, AA Constant Forge |
Himself |
Charles Kiselyak |
Documentary |
2000 |
Up at the Villa |
Rowley Flint |
Philip Haas |
|
2000 |
Before Night Falls |
Cuco Sánchez |
Julian Schnabel |
|
2000 |
Weight of Water, TheThe Weight of Water |
Thomas Janes |
Kathryn Bigelow |
|
2001 |
Dogtown and Z-Boys |
Narrator |
Stacy Peralta |
Documentary |
2001 |
Beaver Trilogy, TheThe Beaver Trilogy |
Groovin' Larry |
Trent Harris |
Segment: "Beaver Kid 2" |
2001 |
Scene Smoking: Cigarettes, Cinema & the Myth of Cool |
Himself |
|
Documentary |
2001 |
Pledge, TheThe Pledge |
— |
Sean Penn |
Writer, director Nominated—Golden Bear Nominated—Bodil Award for Best Non-European Film Nominated—Palme d'Or |
2001 |
See How They Run |
Himself |
|
Documentary |
2001 |
I Am Sam |
Samuel John "Sam" Dawson |
Jessie Nelson |
Nominated—Academy Award for Best Actor Nominated—Broadcast Film Critics Association Award for Best Actor Nominated—Satellite Award for Best Actor - Motion Picture Drama Nominated—Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role |
2002 |
11'09"01 September 11 |
— |
Sean Penn |
Writer, director (segment: "U.S.A.") UNESCO Award Nominated—César Award for Best Film from the European Union |
2003 |
Pauly Shore Is Dead |
Himself |
Pauly Shore |
Cameo |
2003 |
It's All About Love |
Marciello |
Thomas Vinterberg |
|
2003 |
Mystic River |
James "Jimmy" Markum |
Clint Eastwood |
Academy Award for Best Actor Boston Society of Film Critics Award for Best Cast Boston Society of Film Critics Award for Best Actor (2nd place) Broadcast Film Critics Association Award for Best Actor Central Ohio Film Critics Association Award for Best Actor Dallas-Fort Worth Film Critics Association Award for Best Actor Golden Globe Award for Best Actor – Motion Picture Drama Florida Film Critics Circle Award for Best Actor Kansas City Film Critics Circle Award for Best Actor Las Vegas Film Critics Society Award for Best Actor London Film Critics Circle Award for Best Actor Los Angeles Film Critics Award for Best Actor (2nd place) National Board of Review Award for Best Actor New York Film Critics Circle Award for Best Actor (2nd place) Satellite Award for Best Actor - Motion Picture Drama Southeastern Film Critics Association Award for Best Actor (2nd place) Vancouver Film Critics Circle Award for Best Actor Nominated—BAFTA Award for Best Actor in a Leading Role Nominated—Chicago Film Critics Association Award for Best Actor Nominated—Irish Film & Television Award for Best International Actor Nominated—Online Film Critics Society Award for Best Actor Nominated—Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role Nominated—Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture Nominated—Washington D.C. Area Film Critics Association Award for Best Actor |
2003 |
21 Grams |
Paul Rivers |
Alejandro González Iñárritu |
Florida Film Critics Circle Award for Best Actor Las Vegas Film Critics Society Award for Best Actor Los Angeles Film Critics Award for Best Actor (2nd place) National Board of Review Award for Best Actor Phoenix Film Critics Society Award for Best Cast Satellite Award for Best Actor - Motion Picture Drama Volpi Cup Nominated—BAFTA Award for Best Actor in a Leading Role Nominated—Phoenix Film Critics Society Award for Best Actor |
2004 |
Assassination of Richard Nixon, TheThe Assassination of Richard Nixon |
Samuel J. Bicke |
Niels Mueller |
Nominated—Satellite Award for Best Actor - Motion Picture Drama |
2005 |
Interpreter, TheThe Interpreter |
Tobin Keller |
Sydney Pollack |
|
2006 |
All the King's Men |
Willie Stark |
Steven Zaillian |
|
2007 |
Into the Wild |
— |
Sean Penn |
Writer, director Palm Springs International Film Festival Award for Best Director Rome Film Fest Premiere Prize São Paulo International Film Festival Best Foreign Language Film Nominated—Broadcast Film Critics Association Award for Best Director Nominated—BFCA Critics' Choice Award for Best Writer Nominated—Chicago Film Critics Association Award for Best Adapted Screenplay Nominated—Directors Guild of America Award for Best Director – Motion Picture Nominated—Film Critics Circle of Australia Award for Best Foreign Film – English Language Nominated—Writers Guild of America Award for Best Adapted Screenplay |
2007 |
Persepolis |
Marjane's Father |
Marjane Satrapi & Vincent Paronnaud |
Voice, English dub |
2007 |
War Made Easy |
Narrator[4] |
Loretta Alper & Jeremy Earp |
Documentary |
2008 |
What Just Happened |
Himself |
Barry Levinson |
|
2008 |
Tropic Thunder |
Himself |
Ben Stiller |
Cameo |
2008 |
Milk |
Harvey Milk |
Gus Van Sant |
Academy Award for Best Actor Austin Film Critics Association Award for Best Actor Boston Society of Film Critics Award for Best Actor (tied with Mickey Rourke for The Wrestler) Broadcast Film Critics Association Award for Best Actor Broadcast Film Critics Association Award for Best Cast Central Ohio Film Critics Association Award for Best Actor (2nd place) Dallas-Fort Worth Film Critics Association Award for Best Actor Los Angeles Film Critics Award for Best Actor National Society of Film Critics Award for Best Actor New York Film Critics Circle Award for Best Actor Palm Springs International Film Festival Award for Best Actor Phoenix Film Critics Society Award for Best Actor San Francisco Film Critics Circle Award for Best Actor Screen Actors Guild Award for Outstanding Performance by a Male Actor in a Leading Role Southeastern Film Critics Award for Best Actor Vancouver Film Critics Circle Award for Best Actor Nominated—BAFTA Award for Best Actor in a Leading Role Nominated—Chicago Film Critics Association Award for Best Actor Nominated—Golden Globe Award for Best Actor – Motion Picture Drama Nominated—Independent Spirit Award for Best Lead Male Nominated—London Film Critics Circle Award for Best Actor Nominated—MTV Movie Award for Best Kiss Nominated—Online Film Critics Society Award for Best Actor Nominated—Satellite Award for Best Actor - Motion Picture Drama Nominated—Screen Actors Guild Award for Outstanding Performance by a Cast in a Motion Picture Nominated—Toronto Film Critics Association Award for Best Actor |
2008 |
Witch Hunt |
Narrator |
|
Documentary, also executive producer |
2010 |
Fair Game |
Joseph Wilson |
Doug Liman |
|
2011 |
Tree of Life, TheThe Tree of Life |
Adult Jack |
Terrence Malick |
|
2011 |
This Must Be the Place |
Cheyenne |
Paolo Sorrentino |
|
2012 |
Americans |
Commie |
|
Short, also writer |
2013 |
Gangster Squad |
Mickey Cohen |
Ruben Fleischer |
|
2013 |
The Secret Life of Walter Mitty |
Sean O'Connell |
Ben Stiller |
|
2015 |
The Gunman |
Jim Terrier |
Pierre Morel |
|
2016 |
The Last Face |
— |
Sean Penn |
Director; Completed |
2016 |
The Angry Birds Movie |
Terence |
Fergal Reilly & Clay Kaytis |
|