• Summerhood (2006) (in production) (uncredited) .... Narrator
• 1408 (2007) (post-production) .... Mike Enslin
  
• Brand Hauser: Stuff Happens (2007) (post-production)
  
• The Martian Child (2007) (completed)
  
• Cosmic Banditos (2007)
  
• Grace Is Gone (2007) .... Stanley Philipps
  
• The Contract (2006)
  The Ice Harvest (2005) .... Charlie
  Must Love Dogs (2005) .... Jake
  Runaway Jury (2003) .... Nicholas Easter
  Identity (2003) .... Ed
  Max (2002/I) .... Max Rothman
  Serendipity (2001) .... Jonathan Trager
  America's Sweethearts (2001) .... Eddie Thomas
  High Fidelity (2000) .... Rob Gordon
  Being John Malkovich (1999) .... Craig Schwartz
  
• Cradle Will Rock (1999) .... Nelson Rockefeller
  Pushing Tin (1999) .... Nick Falzone
  
• The Jack Bull (1999) (TV) .... Myrl Redding
  The Thin Red Line (1998) .... Captain John Gaff
  
• This Is My Father (1998/I) .... Eddie Sharp, the Pilot
  
• Chicago Cab (1998) .... Scary Man
  Midnight in the Garden of Good and Evil (1997) .... John Kelso
  Anastasia (1997) (voice) .... Dimitri
  Con Air (1997) .... U.S. Marshal Vince Larkin
  Grosse Pointe Blank (1997) .... Martin Q. Blank
  
• "Frasier" .... Greg (1 episode, 1996)
  City Hall (1996) .... Deputy Mayor Kevin Calhoun
  
• The Road to Wellville (1994) .... Charles Ossining
  Bullets Over Broadway (1994) .... David Shayne
  
• Floundering (1994) .... JC
  Money for Nothing (1993) .... Joey Coyle
  
• Map of the Human Heart (1993) .... The Mapmaker
  
• Bob Roberts (1992) .... Cutting Edge Host
  
• Roadside Prophets (1992) (as John Cusak) .... Casper
  
• Shadows and Fog (1992) .... Student Jack
  True Colors (1991) .... Peter Burton
  The Grifters (1990) .... Roy Dillon
  
• Fat Man and Little Boy (1989) .... Michael Merriman
  Say Anything... (1989) .... Lloyd Dobler
  
• Elvis Stories (1989) .... Corky
  Tapeheads (1988) .... Ivan Alexeev
  Eight Men Out (1988) .... George "Buck" Weaver
  
• Broadcast News (1987) (as John Cusak) .... Angry Messenger
  
• Hot Pursuit (1987) .... Dan Bartlett
  One Crazy Summer (1986) .... Hoops McCann
  Stand by Me (1986) .... Denny Lachance
  
• The Journey of Natty Gann (1985) .... Harry
  Better Off Dead... (1985) .... Lane Meyer
  The Sure Thing (1985) .... Walter (Gib) Gibson
  
• Grandview, U.S.A. (1984) .... Johnny Maine
  Sixteen Candles (1984) .... Bryce
  Class (1983) .... Roscoe Maibaum