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| Movie | Middle Men | Jack Harris | 2010.08.06 |
| Movie | Henry Poole Is Here | Henry Poole | 2008.08.15 |
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| Movie | You Kill Me | Tom | 2007.07.13 |
| Movie | Vacancy | David Fox | 2007.04.20 |
| Movie | My Super Ex-Girlfriend | Matt Saunders | 2006.07.21 |
| Movie | The Family Stone | Ben Stone | 2005.12.16 |
| Movie | Old School | Mitch | 2003.02.21 |
| Movie | Alex & Emma | Alex Sheldon / Adam Shipley | 2003.06.20 |
| Movie | Charlie's Angels: Full Throttle | Pete | 2003.06.27 |
| Movie | Legally Blonde 2: Red, White & Blonde | Emmett Richmond | 2003.07.02 |
| Movie | The Royal Tenenbaums | Richie Tenenbaum | 2002.01.04 |
| Movie | Soul Survivors | Jude | 2001.09.07 |
| Movie | Legally Blonde | Emmett | 2001.07.13 |
| Movie | My Dog Skip | Dink | 2000.03.03 |
| Movie | Charlie's Angels | Pete Komisky | 2000.11.03 |
| Movie | Rushmore | Dr. Peter Flynn | 1999.02.19 |
| Movie | Blue Streak | Carlson | 1999.09.17 |