Chris Penn
- Aftermath
2013 Tony Bricker
- The Darwin Awards
2007 Tom
- King of Sorrow
2007 Detective Enola
- Holly
2006 Freddie
- Best of Chris Isaak
2006 (segment "Somebody's Crying") (archive footage) (uncredited)
- After the Sunset
2004 Rowdy Fan
- Starsky & Hutch
2004 Manetti
- Grand Theft Auto: San Andreas - The Introduction
2004 Pulaski (voice)
- Footloose: A Modern Musical
2004 Thanks
- American Pie: Revealed
2004 Stifler's Dad
- Masked and Anonymous
2003 Crew Guy #2
- Shelter Island
2003 Sheriff Deluca
- Murder by Numbers
2002 Ray Feathers
- Stealing Harvard
2002 David Loach
- Redemption
2002 Tony Leggio
- Kiss Kiss (Bang Bang)
2001 Bubba
- Corky Romano
2001 Peter Romano
- Cement
2000 Bill Holt
- Bread and Roses
2000 Party Guest (uncredited)
- The Florentine
1999 Bobbie
- Rush Hour
1998 Clive
- Papertrail
1998 FBI Agent Jason Enola
- One Tough Cop
1998 Duke Finnerly
- Family Attraction
1998 Father
- Flagpole Special
1998
- Deceiver
1997 Detective Phillip Braxton
- Mulholland Falls
1996 Arthur Relyea
- The Funeral
1996 Chez Tempio
- The Boys Club
1996 Luke
- Sacred Cargo
1996 Vince Kanevsky
- Fist of the North Star
1995 Jackal
- Under the Hula Moon
1995 Turk Dickson
- To Wong Foo, Thanks for Everything! Julie Newmar
1995 Sheriff Dollard
- Imaginary Crimes
1994 Jarvis
- Who Do You Think You're Fooling?
1994 Eddie Cabot (archive footage)
- True Romance
1993 Nicky Dimes
- Short Cuts
1993 Jerry Kaiser
- Beethoven's 2nd
1993 Floyd
- Best of the Best 2
1993 Travis Brickley
- The Pickle
1993 Gregory Stone
- The Music of Chance
1993 Floyd
- Josh & S.A.M.
1993 Derek Baxter
- Reservoir Dogs
1992 "Nice Guy" Eddie Cabot
- Leather Jackets
1992 Big Steve
- Future Kick
1991 Bang
- Mobsters
1991 Tommy Reina
- Return from the River Kwai
1989 Lieutenant Crawford
- Best of the Best
1989 Travis Brickley
- Made in U.S.A.
1987 Tuck
- Faerie Tale Theatre: Rip Van Winkle
1987 Will Tussenbrook
- At Close Range
1986 Thomas 'Tommy' Whitewood
- Pale Rider
1985 Josh LaHood
- North Beach and Rawhide
1985 Dan Donnelly
- Footloose
1984 Willard
- The Wild Life
1984 Tom Drake
- Rumble Fish
1983 B.J. Jackson
- All the Right Moves
1983 Brian Riley
- Charlie and the Talking Buzzard
1979 Pete (as Christopher Penn)
