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| Fred Claus |
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| Fred Claus was released in 2007 in which he played the role of Fred Claus. |
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| 2 |
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| Into the Wild |
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| Into the Wild was released in 2007 and in which he played the role of Wayne Westerberg. |
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| 3 |
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| The Break-Up |
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| The Break-Up was released in 2006 and in which he played the role of Gary Grobowski. |
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| 4 |
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| Wedding Crashers |
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| Wedding Crashers was released in 2005 and in which he played the role of Jeremy Grey. |
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| 5 |
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| Mr. & Mrs. Smith |
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| Mr. & Mrs. Smith was released in 2005 and in which he played the role of Eddie. |
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| 6 |
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| Be Cool |
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| Be Cool was released in 2005 and in which he played the role of Raji. |
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| 7 |
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| Thumbsucker |
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| Thumbsucker was released in 2005 and in which he played the role of Mr. Geary. |
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| 8 |
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| Anchorman: The Legend of Ron Burgundy |
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| Anchorman: The Legend of Ron Burgundy was released in 2004 and in which he played the role of Wes Mantooth. |
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| 9 |
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| Dodgeball: A True Underdog Story |
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| Dodgeball: A True Underdog Story was released in 2004 and in which he played the role of Peter La Fleur. |
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| 10 |
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| Starsky & Hutch |
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| Starsky & Hutch was released in 2004 and in which he played the role of Reese Feldman. |
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| 11 |
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| I Love Your Work |
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| I Love Your Work was released in 2003 and in which he played the role of Stiev. |
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| 12 |
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| Blackball |
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| Blackball was released in 2003 and in which he played the role of Rick Schwartz. |
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| 13 |
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| Old School |
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| Old School was released in 2003 and in which he played the role of Bernard 'Beanie' Campbell. |
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| 14 |
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| Domestic Disturbance |
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| Domestic Disturbance was released in 2001 and in which he played the role of Rick Barnes. |
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| 15 |
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| Zoolander |
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| Zoolander was released in 2001 and in which he played the role of Luke Zoolander. |
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| 16 |
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| Made |
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| Made wass released in 2001 and in which he played the role of Ricky Slade |
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| 17 |
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| The Prime Gig |
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| The Prime Gig was released in 2000 and in which he played the role of Pendelton 'Penny' Wise. |
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| 18 |
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| The Cell |
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| The Cell was released in 2000 and in which he played the role of FBI Agent Peter Novak. |
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| 19 |
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| South of Heaven, West of Hell |
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| South of Heaven, West of Hell was released in 2000 and in which he played the role of Taylor Henry. |
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| 20 |
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| Psycho |
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| Psycho was released in 1998 and in which he played the role of Norman Bates. |
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