| 2014 | | FuryFury(2014) | Wardaddy | - |
| 2013 | | 12 Years a Slave12 Years a Slave(2013) | Henry B. Northup | - |
| 2013 | | Dirty TricksDirty Tricks(2013) | John Dean | - |
| 2013 | | The CounselorThe Counselor(2013) | Westray | - |
| 2013 | | World War ZWorld War Z(2013) | Gerry Lane | - |
| 2012 | | 88(2012) | Chief Judge Vaughn R. Walker | - |
| 2012 | | Killing Them SoftlyKilling Them Softly(2012) | Jackie Cogan | - |
| 2011 | | Happy Feet TwoHappy Feet Two(2011) | Will the Krill (voice) | - |
| 2011 | | MoneyballMoneyball(2011) | Billy Beane | - |
| 2011 | | The Tree of LifeThe Tree of Life(2011) | Mr. O'Brien | - |
| 2010 | | MegamindMegamind(2010) | Metro Man (voice) | - |
| 2009 | | Inglourious BasterdsInglourious Basterds(2009) | Lt. Aldo Raine | - |
| 2008 | | Burn After ReadingBurn After Reading(2008) | Chad Feldheimer | - |
| 2008 | | The Curious Case of Benjamin ButtonThe Curious Case of Benjamin Button(2008) | Benjamin Button | - |
| 2007 | | Ocean's ThirteenOcean's Thirteen(2007) | Robert “Rusty” Charles Ryan | - |
| 2007 | | The Assassination of Jesse James by the Coward Robert FordThe Assassination of Jesse James by the Coward Robert Ford(2007) | Jesse James | - |
| 2006 | | BabelBabel(2006) | Richard | - |
| 2005 | | Mr. & Mrs. SmithMr. & Mrs. Smith(2005) | John Smith | - |
| 2004 | | Ocean's TwelveOcean's Twelve(2004) | Rusty Ryan | - |
| 2004 | | TroyTroy(2004) | Achilles | - |
| 2003 | | Sinbad: Legend of the Seven SeasSinbad: Legend of the Seven Seas(2003) | Sinbad | - |
| 2002 | | Confessions of a Dangerous MindConfessions of a Dangerous Mind(2002) | Brad 1st Bachelor | - |
| 2002 | | Full FrontalFull Frontal(2002) | Himself | - |
| 2002 | | Ultimate Fights from the MoviesUltimate Fights from the Movies(2002) | Mickey O'Neil (Snatch) (archive footage) | - |
| 2001 | | Ocean's ElevenOcean's Eleven(2001) | Rusty Ryan | - |
| 2001 | | Spy GameSpy Game(2001) | Tom Bishop | - |
| 2001 | | The MexicanThe Mexican(2001) | Jerry Welbach | - |
| 2000 | | Snatch.Snatch.(2000) | Mickey O'Neil | - |
| 1999 | | Being John MalkovichBeing John Malkovich(1999) | Himself | - |
| 1999 | | Fight ClubFight Club(1999) | Tyler Durden | - |
| 1998 | | Meet Joe BlackMeet Joe Black(1998) | Joe Black | - |
| 1997 | | Seven Years in TibetSeven Years in Tibet(1997) | Heinrich Harrer | - |
| 1997 | | The Devil's OwnThe Devil's Own(1997) | Frankie McGuire | - |
| 1996 | | SleepersSleepers(1996) | Michael Sullivan | - |
| 1995 | | Se7enSe7en(1995) | Detective David Mills | - |
| 1995 | | Twelve MonkeysTwelve Monkeys(1995) | Jeffrey Goines | - |
| 1994 | | Interview with the VampireInterview with the Vampire(1994) | Louis de Pointe du Lac | - |
| 1994 | | Legends of the FallLegends of the Fall(1994) | Tristan Ludlow | Young Isabel Two |
| 1994 | | The FavorThe Favor(1994) | Elliott Fowler | - |
| 1993 | | KaliforniaKalifornia(1993) | Early Grayce | - |
| 1993 | | True RomanceTrue Romance(1993) | Floyd | - |
| 1992 | | A River Runs Through ItA River Runs Through It(1992) | Paul Maclean | - |
| 1992 | | Cool WorldCool World(1992) | Detective Frank Harris | - |
| 1991 | | Across the TracksAcross the Tracks(1991) | Joe Maloney | - |
| 1991 | | Johnny SuedeJohnny Suede(1991) | Johnny Suede | - |
| 1991 | | Thelma & LouiseThelma & Louise(1991) | J.D. | - |
| 1990 | | Too Young to Die?Too Young to Die?(1990) | Billy Canton | - |
| 1989 | | Cutting ClassCutting Class(1989) | Dwight Ingalls | - |
| 1989 | | Happy TogetherHappy Together(1989) | Brian | - |
| 1988 | | The Dark Side of the SunThe Dark Side of the Sun(1988) | Rick | - |
