- Red Rue Express
2026 himself
- Black Sunflowers
2026 Executive Producer
- Animals in War
2025
- One Battle After Another
2025 Col. Steven J. Lockjaw
- Words of War
2025 Executive Producer
- Manas
2025 Executive Producer
- Asphalt City
2024 Producer
- Daddio
2024 Clark
- September 5
2024 Producer
- Superpower
2023 Director
- Gonzo Girl
2023
- Licorice Pizza
2021 Jack Holden
- Flag Day
2021 Director
- kid 90
2021 Executive Producer
- Fast Times at Ridgemont High: A Virtual Table Read
2020 Pizza Guy
- The Professor and the Madman
2019 Dr. William Chester Minor
- Sound of Sun
2017 Man
- Mad Hannans
2017
- The Last Face
2017 Director
- The Angry Birds Movie
2016 Terence (voice)
- The Human Experiment
2015 Executive Producer
- The Gunman
2015 Screenplay
- Gangster Squad
2013 Mickey Cohen
- The Secret Life of Walter Mitty
2013 Sean O'Connell
- Haiti Untold
2012
- Americans
2012 Story
- The Tree of Life
2011 Jack
- This Must Be the Place
2011 Cheyenne
- I'm Still Here
2010 Sean Penn (uncredited)
- Fair Game
2010 Joseph Wilson
- Deflating the Elephant
2009 Narrator
- Where the Wild Things Are
2009 Thanks
- Milk
2008 Harvey Milk
- What Just Happened
2008 Sean Penn
- War Made Easy
2007 Narrator (Voice)
- Into the Wild
2007 Director
- All the King's Men
2006 Willie Stark
- The Interpreter
2005 Tobin Keller
- The Assassination of Richard Nixon
2004 Samuel Bicke
- Mystic River
2003 Jimmy Markum
- 21 Grams
2003 Paul Rivers
- It's All About Love
2003 Marciello
- Pauly Shore Is Dead
2003 Sean Penn
- This So-Called Disaster
2003 Ray
- Dogtown and Z-Boys
2002 Narrator
- September 11
2002 Director
- I Am Sam
2001 Sam Dawson
- The Weight of Water
2001 Thomas Janes
- The Pledge
2001 Director
- Before Night Falls
2000 Cuco Sanchez
- Beaver Trilogy
2000 "Groovin' Larry" Huff
- Up at the Villa
2000 Rowley Flint
- Sweet and Lowdown
1999 Emmet Ray
- Being John Malkovich
1999 Sean Penn (uncredited)
- Hurlyburly
1998 Eddie
- The Thin Red Line
1998 1st Sgt. Edward Welsh
- U Turn
1997 Bobby Cooper
- The Game
1997 Conrad Van Orton
- Hugo Pool
1997 Strange Hitchhiker
- She's So Lovely
1997 Executive Producer
- Loved
1997 Producer
- Dead Man Walking
1995 Matthew Poncelet
- The Crossing Guard
1995 Director
- Carlito's Way
1993 David Kleinfeld
- Cruise Control
1992
- The Indian Runner
1991 Director
- State of Grace
1990 Terry
- Cool Blue
1990 Phil the Plumber (uncredited)
- Casualties of War
1989 Sgt. Tony Meserve
- We're No Angels
1989 Jim
- Colors
1988 Danny McGavin
- Judgment in Berlin
1988 Guenther X
- Dear America: Letters Home from Vietnam
1987 (voice)
- At Close Range
1986 Bradford 'Brad' Whitewood Jr.
- Shanghai Surprise
1986 Glendon Wasey
- The Falcon and the Snowman
1985 Daulton Lee
- Racing with the Moon
1984 Henry 'Hopper' Nash
- Crackers
1984 Dillard
- Bad Boys
1983 Mick O'Brien
- Summerspell
1983 Buddy
- Risky Business
1983 Passenger in Car (uncredited)
- Fast Times at Ridgemont High
1982 Jeff Spicoli
- Taps
1981 Cadet Captain Alex Dwyer
- The Killing of Randy Webster
1981 Don Fremont
- The Beaver Kid 2
1981 Groovin' Larry
- Hellinger's Law
1981 Bit Part (uncredited)
- Candles
Set Decoration
- Untitled Jamal Khashoggi Project
Director
- Untitled Sean Penn Film
Director
- The Gun on Second Street
Executive Producer
- Untitled Sean Penn Film
Director
