| Year | Title | Role | Notes |
| 1997 | Pleasant Grove | Bedford | Short film |
| 1998 | Physical Pinball | - | Short film |
| 2000 | George Washington | Rico Rice | - |
| 2003 | Security, Colorado | Paul | Filmed in the Dogme 95 style. |
| 2003 | All the Real Girls | Paul | Writer |
| 2003 | Crude | Gabe | - |
| 2004 | 50 Ways to Leave Your Lover | Owen McCabe | - |
| 2005 | Elizabethtown | Jesse Baylor | - |
| 2005 | The Family Stone | Brad Stevenson | - |
| 2006 | Live Free or Die | Jeff Lagrand | - |
| 2007 | The Assassination of Jesse James by the Coward Robert Ford | Dick Liddil | - |
| 2007 | Lars and the Real Girl | Gus | - |
| 2008 | Pretty Bird | Beach Dog Jogger | Writer, director |
| 2009 | Bright Star | Charles Armitage Brown | - |
| 2009 | Away We Go | Courtney Farlander | - |
| 2011 | Water for Elephants | Charlie O'Brien | - |
| 2011 | The Beloved | Henderson | - |
| 2012 | Flowers of War | Terry | - |
| 2012 | The Babymakers | Tommy Macklin | - |
| 2013 | Hello Carter | Aaron | - |
| 2014 | Goodbye to All That | Otto Wall | - |
| 2014 | Black Eyed Dog | - | - |
| 2014 | Straight Men/Same Bed | - | Short film Writer, director, producer |
| 2015 | The Daughter | Christian | - |
| 2016 | Café Society | Steve | - |
| 2016 | Rules Don't Apply | Richard Miskin | - |
| TBA | The Sound of Philadelphia | - | Filming |