| 1993 | My Boyfriend's Back | Teenage Moviegoer | |
| 1993 | Dazed and Confused | David Wooderson | |
| 1994 | Angels in the Outfield | Ben Williams | |
| 1995 | Texas Chainsaw Massacre: The Next Generation | Vilmer | limited release |
| Boys on the Side | Officer Abe Lincoln | |
| 1996 | A Time to Kill | Jake Tyler Brigance | |
| Lone Star | Buddy Deeds | |
| Glory Daze | Rental Truck Guy | |
| Larger Than Life | Tip Tucker | |
| Scorpion Spring | El Rojo | |
| 1997 | Amistad | Baldwin | |
| Contact | Palmer Joss | |
| 1998 | The Newton Boys | Willis Newton | |
| 1999 | EDtv | Ed 'Eddie' Pekurny | |
| 2000 | U-571 | Lt. Andrew Tyler, Executive Officer | |
| 2001 | The Wedding Planner | Steve "Eddie" Edison | |
| 2002 | Reign of Fire | Denton Van Zan | |
| Thirteen Conversations About One Thing | Troy | |
| Frailty | Adam Meiks | |
| 2003 | How to Lose a Guy in 10 Days | Benjamin 'Ben' Barry | |
| 2004 | Paparazzi | Himself | |
| 2005 | Two for the Money | Brandon Lang | |
| Sahara | Dirk Pitt | |
| 2006 | We Are Marshall | Jack Lengyel | |
| Failure to Launch | Tripp | |
| 2008 | Fool's Gold | Ben 'Finn' Finnegan | |
| Tropic Thunder | TBA | August 2008 |
| Surfer Dude | Steve Addington | Awaiting release |
| 2009 | The Ghosts of Girlfriends Past | Connor | Filming |
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