| Year | Title | Role | Notes |
| 1997 | Hercules | Young Hercules (singing voice) | - |
| 1999 | The Insider | Seelbach Hotel Manager | - |
| 2001 | Lady and the Tramp II: Scamp's Adventure | Scamp (singing voice) | Direct-to-Video |
| 2004 | The Stepford Wives | Roger Bannister | remake of the 1975 film |
| 2005 | The Producers | Carmen Ghia | based on the 1968 musical |
| 2006 | I Want Someone to Eat Cheese With | Burl Cannalo | - |
| 2007 | Hostel: Part II | Stuart | - |
| 2007 | American Gangster | U.S. Attorney | - |
| 2008 | Spy School | Principal Hampton | - |
| 2008 | Harold & Kumar Escape from Guantanamo Bay | Dr. Beecher | - |
| 2008 | The Midnight Meat Train | Jurgis | - |
| 2009 | Law Abiding Citizen | Brian Bringham | - |
| 2011 | One Night Stand | Himself | - |
| 2012 | Excision | Bob | - |
| 2012 | Freaky Deaky | Jerry Baker | - |
| 2012 | A Green Story | Johnson | - |
| 2012 | The Producers | Carmen Ghia | Direct-to-Video |
| 2012 | Smiley | Professor Clayton | - |
| 2012 | The Last Man | Will | Short film |
| 2013 | April Apocalypse | Jack | - |
| 2013 | Last Vegas | Maurice Tischler | - |
| 2015 | Molly | Brad | Short film |
| 2015 | Trumbo | Buddy Ross | - |
| 2016 | Internet Famous | Chris! | - |
| 2017 | Speech & Date | Principal Bellingham | - |
| 2018 | Ghost Light | Henry Asquith | - |
| 2019 | Bayou Tales | Adam | filming |
| TBA | Butterfly in the Typewriter | Les Phillabaum | pre-production |
| TBA | Broadway: The Next Generation | Himself | Documentary filming |