1983 ~*~ Class ~*~ Roscoe
1984 ~*~ Sixteen Candles ~*~ Bryce
1984 ~*~ Grandview, U.S.A. ~*~ Johnny Maine
1985 ~*~ The Sure Thing ~*~ Walter (Gib) Gibson
1985 ~*~ The Journey of Natty Gann ~*~ Harry
1985 ~*~ Better Off Dead ~*~ Lane Myer
1986 ~*~ Stand By Me ~*~ Denny Lachance
1986 ~*~ One Crazy Summer ~*~ Hoops McCann
1987 ~*~ Hot Pursuit ~*~ Dan Bartlett
1987 ~*~ Broadcast News ~*~ Angry Messenger
1988 ~*~ Tapeheads ~*~ Ivan Alexeev
1988 ~*~ Eight Men Out ~*~ Buck Weaver
1989 ~*~ Say Anything... ~*~ Lloyd Dobler
1989 ~*~ Fat Man and Little Boy (aka Shadow Makers) ~*~ Michael Merriman
1989 ~*~ Elvis Stories ~*~ Corky
1990 ~*~ The Grifters ~*~ Roy Dillon
1991 ~*~ True Colors ~*~ Peter Burton
1992 ~*~ Shadows and Fog ~*~ Student Jack
1992 ~*~ The Player ~*~ Himself
1992 ~*~ Bob Roberts ~*~ Cutting Edge Host
1992 ~*~ Roadside Prophets ~*~ Casper
1992 ~*~ Map of the Human Heart ~*~ The mapmaker
1993 ~*~ Money for Nothing ~*~ Joey Coyle
1994 ~*~ Bullets Over Broadway ~*~ David Shayne
1994 ~*~ "Baseball" mini TV series ~*~ Himself (voice)
1994 ~*~ The Road to Wellville ~*~ Charles Ossining
1994 ~*~ Floundering ~*~ JC
1996 ~*~ City Hall ~*~ Deputy Major Kevin Calhoun
1997 ~*~ Grosse Pointe Blank ~*~ Martin Q. "Marty" Blank
1997 ~*~ Con Air ~*~ U.S. Marshal Vince Larkin
1997 ~*~ Eastwood on Eastwood (TV) ~*~ Narrator
1997 ~*~ Midnight In The Garden Of Good And Evil ~*~ John Kelso
1997 ~*~ Anastasia ~*~ Dimitri (voice)
1998 ~*~ Chicago Cab (aka Hellcab, US video title) ~*~ Scary Man
1998 ~*~ This Is My Father ~*~ Eddie Sharp, the pilot
1998 ~*~ The Thin Red Line ~*~ Captain John Gaff
1999 ~*~ The Jack Bull (TV) ~*~ Myrl Redding
1999 ~*~ Pushing Tin ~*~ Nick Falzone
1999 ~*~ Cradle Will Rock ~*~ Nelson Rockefeller
1999 ~*~ Being John Malkovich ~*~ Craig Schwartz
2000 ~*~ Life of the Party ~*~ -------
2000 ~*~ Arigo ~*~ -------
2000 ~*~ High Fidelity ~*~ Rob Gordon
2001 ~*~ America's Sweethearts ~*~ Eddie Thomas
2001 ~*~ Serendipity ~*~ Jonathan Trager
2001 ~*~ America: A Tribute To Heros (TV) ~*~ Himself
2001 ~*~ Concert For New York City (TV) ~*~ Himself
2002 ~*~ Adaptation ~*~ Himself
2002 ~*~ Max (aka Hoffman) ~*~ Max Rothman
2003 ~*~ Identity (aka I.D.) ~*~ Ed
2003 ~*~ The Runaway Jury ~*~ Nicholas Easter/Jeff Kerr
