Cosmic Banditos (2002) 
Adaptation (2001) .... Himself 
Serendipity (2001) .... Jonathan Trager 
America's Sweethearts (2001) .... Eddie Thomas 
High Fidelity (2000) .... Rob 


Being John Malkovich (1999) .... Craig Schwartz 
Cradle Will Rock (1999) .... Nelson Rockefeller 
Pushing Tin (1999) .... Nick Falzone 
Thin Red Line, The (1998) .... Captain John Gaff 
This Is My Father (1998) .... Eddie Sharp, the Pilot 
Chicago Cab (1998) .... Scary Man 
Anastasia (1997) (voice) .... Dimitri 
Midnight in the Garden of Good and Evil (1997) .... John Kelso 
Con Air (1997) .... Vince Larkin 
Grosse Pointe Blank (1997) .... Martin Q. 'Marty' Blank 
City Hall (1996) .... Kevin Calhoun 
Floundering (1994) .... JC 
Road to Wellville, The (1994) .... Charles Ossining 
Bullets Over Broadway (1994) .... David Shayne 
Money for Nothing (1993/I) .... Joey Coyle 
Bob Roberts (1992) .... Cutting Edge Host 
Map of the Human Heart (1992) .... The Mapmaker 
Roadside Prophets (1992) .... Serial Eater 
Player, The (1992) .... Himself 
Shadows and Fog (1992) .... Student Jack 
True Colors (1991) .... Peter Burton 
Grifters, The (1990) .... Roy Dillon 


Elvis Stories (1989) .... Corky 
Fat Man and Little Boy (1989) .... Michael Merriman 
Say Anything... (1989) .... Lloyd Dobler 
Eight Men Out (1988) .... Buck Weaver 
Tapeheads (1988) .... Ivan Alexeev 
Broadcast News (1987) .... Angry Messenger 
Hot Pursuit (1987) .... Dan Bartlett 
One Crazy Summer (1986) .... Hoops McCann 
Stand by Me (1986) .... Denny Lachance 
Better Off Dead... (1985) .... Lane Myer 
Journey of Natty Gann, The (1985) .... Harry 
Sure Thing, The (1985) .... Walter (Gib) Gibson 
Grandview, U.S.A. (1984) .... Johnny Maine 
Sixteen Candles (1984) .... Bryce 
Class (1983) .... Roscoe