Filmography
| Year | Title | Role | Notes |
|---|---|---|---|
| 1983 | The Right Stuff | Dwight D. Eisenhower (voice) | uncredited |
| 1987 | Million Dollar Mystery | Officer Quinn | first credited role in a motion picture |
| 1988 | Willow | Rool | |
| 1990 | Coming of Age | Brian Brinker | television series |
| 1990 | Avalon | Izzy Kirk | |
| 1991 | L.A. Story | Frank Swan | |
| 1991 | Another You | Phil | |
| 1991 | Morton & Hayes | Chick Morton | television series |
| 1991 | Ricochet | Larry Doyle | |
| 1992 | The Opposite Sex and How to Live with Them | Eli | |
| 1992 | A Few Good Men | Lt. Sam Weinberg | |
| 1993 | Indian Summer | Brad Berman | |
| 1993 | Wayne's World 2 | Jerry Segel | |
| 1993 | Grumpy Old Men | Jacob Goldman | |
| 1994 | ExtraTERRORestrial Alien Encounter | Spinlok | Disney World Ride (has since been replaced with Stitch's Great Escape!) |
| 1994 | Clean Slate | Rosenheim | |
| 1995 | Usual Suspects, TheThe Usual Suspects | Todd Hockney | National Board of Review Award for Best Cast |
| 1995 | Miami Rhapsody | Jordan Marcus | |
| 1995 | Canadian Bacon | Stu Smiley | |
| 1995 | Casino | Phillip Green | |
| 1995 | Grumpier Old Men | Jacob Goldman | |
| 1995 | Chameleon | Matt Gianni | |
| 1995 | The Drew Carey Show | Mr. Bell | television series, 1st season only |
| 1996 | House Arrest | Ned Beindorf | |
| 1996 | That Thing You Do! | Victor 'Boss Vic Koss' Kosslovich | |
| 1997 | Truth or Consequences, N.M. | Gordon Jacobson | |
| 1998 | Buffalo '66 | TV Sportscaster | |
| 1998 | From the Earth to the Moon | Joe Shea | Nominated - Satellite Award for Best Actor – Miniseries or Television Film |
| 1998 | Hoods | Rudy | |
| 1999 | Outside Ozona | Wit Roy | |
| 1999 | Deal of a Lifetime | Jerry | |
| 1999 | She's All That | Wayne Boggs | |
| 1999 | The Sex Monster | Dr. Jerry Berman | |
| 1999 | Deterrence | President Walter Emerson | |
| 1999 | End of Days | Bobby Chicago | Nominated — Blockbuster Entertainment Award for Favorite Supporting Actor (Action/Science-Fiction) |
| 1999 | Work with Me | Jordan Better | television series |
| 2000 | The Whole Nine Yards | Janni Pytor Gogolak | |
| 2000 | Steal This Movie! | Gerry Lefcourt | |
| 2001 | The Wedding Planner | Dr. John Dojny | |
| 2001 | 3000 Miles to Graceland | Damitry | |
| 2001 | Dr. Dolittle 2 | Riley/Alligator | |
| 2002 | Stolen Summer | Rabbi Jacobsen | |
| 2002 | Frank McKlusky, C.I. | Ronnie Rosengold | |
| 2002 | Juwanna Mann | Lorne Daniels | |
| 2002 | Mother Ghost | Dr. Norris | |
| 2002 | The Santa Clause 2 | Cupid | |
| 2003 | Rolling Kansas | Agent Brinkley | uncredited |
| 2003 | Blizzard | Archimedes | |
| 2004 | Seven Times Lucky | Harlan | |
| 2004 | The Whole Ten Yards | Lazlo Gogolak | |
| 2004 | Our Time is Up | Dr. Stern | Nominated for Academy Award for Live Action Short Film |
| 2005 | Hostage | Walter Smith | |
| 2005 | Magnificent Desolation: Walking on the Moon 3D | Director (Voice) | |
| 2005 | The Aristocrats | Himself | |
| 2006 | The Santa Clause 3: The Escape Clause | Cupid | |
| 2006 | The Lost Room | Karl Kreutzfeld | mini-series |
| 2007 | Numb | Tom | |
| 2007 | Shark | D.A. Leo Cutler | television series |
| 2008 | Otis | Eli | |
| 2008 | Picture This | Tom Gilbert | straight to DVD |
| 2008 | Tortured | Dr. Shaw | straight to DVD |
| 2008 | Entourage | Mr. Bob Levine | television series, episode 503 - The All Out Fall Out |
| 2009 | 2:13 | Walter Smith | |
| 2009 | Middle Men | Curt Allmans | |
| 2010 | Columbus Circle | Klandermann | co-writer & co-executive producer |
| 2010 | Cop Out | Hunsaker | |
| 2010 | Vamped Out | Elliot Finke | web series (also director, creator, writer, and producer) |
| 2011 | Choose | Sheriff Tom Wagner | |
| 2011 | Red State | ASAC Brooks | |
| 2011 | The Big Year | Eli | |
| 2012 | Geezers! | Kevin | post-production |
| 2012 | Chez Upshaw | filming | |
| 2012 | Men at Work | Pavel | television series, episode 105 - Toilet of Eden |
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