| Movie | Role |
|---|---|
| Patch Adams (1998) | Mitch Roman |
| Happiness (1998) | Allen |
| The Big Lebowski (1998) | Brandt |
| The Talented Mr. Ripley (1999) | Freddie Miles |
| 25th Hour (2002) | Jacob Elinsky |
| Mary and Max (2009) | Max Jerry Horovitz (voice) |
| Magnolia (1999) | Phil Parma |
| Synecdoche, New York (2008) | Caden Cotard |
| Moneyball (2011) | Art Howe |
| The Master (2012) | Lancaster Dodd |
| Punch-Drunk Love (2002) | Dean Trumbell |
| Scent of a Woman (1992) | George Willis, Jr. |
| Mission: Impossible III (2006) | Owen Davian |