To explain the "should have seen" label, it basically means that I've
had opportunities to see it but for one reason or another, did not.
| Year | Film | Role |
|---|---|---|
| 1983 | Class | Roscoe Maibaum |
| 1984 | Bryce | |
| Grandview, U.S.A. | Johnny Maine | |
| 1985 | The Sure Thing | Walter (Gib) Gibson |
| The Journey of Natty Gann | Harry | |
| Lane Meyer | ||
| 1986 | Denny Lachance | |
| One Crazy Summer | Hoops McCann | |
| 1987 | Hot Pursuit | Dan Bartlett |
| Broadcast News | Angry Messenger | |
| 1988 | Eight Men Out | George 'Buck' Weaver |
| Tapeheads | Ivan Alexeev | |
| 1989 | Elvis Stories | Corky |
| Lloyd Dobler | ||
| Fat Man and Little Boy | Michael Merriman | |
| 1990 | The Grifters | Roy Dillon |
| 1991 | True Colors | Peter Burton |
| 1992 | Shadows and Fog | Student Jack |
| The Player | Self | |
| Bob Roberts | Cutting Edge Host | |
| Roadside Prophets | Caspar | |
| 1993 | Map of the Human Heart | The Mapmaker |
| Money for Nothing | Joey Coyle | |
| 1994 | Floundering | JC |
| Bullets Over Broadway | David Shayne | |
| The Road to Wellville | Charles Ossining | |
| 1996 | City Hall | Deputy Mayor Kevin Calhoun |
| 1997 | Martin Q. Blank | |
| U.S. Marshal Vince Larkin | ||
| Dimitri | ||
| Midnight in the Garden of Good and Evil | John Kelso | |
| 1998 | Chicago Cab | Scary man |
| This Is My Father | Eddie Sharp, the Pilot | |
| The Thin Red Line | Capt. Gaff | |
| 1999 | Pushing Tin | Nick Falzone |
| Cradle Will Rock | Nelson Rockefeller | |
| Being John Malkovich | Craig Schwartz | |
| The Jack Bull | Myrl Redding | |
| 2000 | Rob Gordon | |
| 2001 | Eddie Thomas | |
| Jonathan Trager | ||
| 2002 | Max | Max Rothman |
| Adaptation. | Himself | |
| 2003 | Ed Dakota | |
| Breakfast With Hunter | Himself | |
| Runaway Jury | Nicholas Easter | |
| 2005 | Must Love Dogs | Jake Anderson |
| The Ice Harvest | Charlie Arglist | |
| 2006 | Buy the Ticket, Take the Ride: Hunter S. Thompson on Film | Himself |
| The Contract | Ray Keene | |
| 2007 | Martian Child | David Gordon |
| Mike Enslin | ||
| Grace Is Gone | Stanley Philipps | |
| 2008 | War, Inc. | Brand Hauser |
| Summerhood | Narrator | |
| Igor | Igor | |
| 2009 | 2012 | Jackson Curtis |
| 2010 | Shanghai | Paul Soames |
| The Factory | Mike Fletcher | |
| Hot Tub Time Machine |







