 | Darla in Space (2024) as Arnot Pickens |
 | Ghostwritten (2022) as Martin Cline |
 | Cryptozoo (2021) as Nicholas (voice) |
 | Scenes from an Empty Church (2021) as Father James |
 | The Return of Tragedy (2020) as Chief of Police |
 | Dedalus (2018) as William |
 | My Entire High School Sinking Into the Sea (2016) as Principal Grimm (voice) |
 | Burn Country (2016) as Dmitri Sokurov |
 | The Missing Girl (2015) as Stan Colvins |
 | Equals (2015) as Gideon |
 | Ned Rifle (2015) as Henry Fool |
 | My America (2014) |
 | Sabbatical (2014) as Dan Keaton |
 | The Dollar General (2011) as James Baldwin |
| | Years Later: The Unbelievable Truth and Its Consequences (2010) as Himself |
 | My Sweet Misery (2009) as Psychologist |
 | Dream Boy (2008) as Harland Davies |
 | South of Heaven (2008) as Hood 2 |
 | The Making of 'Fay Grim' or: How Do You Spell Espionage? (2007) as Himself |
 | Fay Grim (2007) as Henry Fool |
 | Strange Culture (2007) as Steve Kurtz |
 | The Attic (2006) as Dr. Perry |
 | The Dying Gaul (2005) |
 | The Pigs (2005) as Larry |
 | Tiger: His Fall & Rise (2004) as Joe Luck |
 | Eternal Sunshine of the Spotless Mind (2004) as Frank |
| | The Cloud of Unknowing (2002) |
 | New World Order (2002) as Zeus |
 | Teknolust (2002) as Preacher |
| | Dischord (2001) as Jimmy |
 | The Legend of Bagger Vance (2000) as Spec Hammond |
 | Mary Cassatt: American Impressionist (1999) as Edgar Degas |
 | The Book of Life (1998) as Satan |
 | Henry Fool (1998) as Henry Fool |
 | Degas and the Dancer (1998) as Edgar Degas |
