| 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 | |