- 2008: Co-starred with Reese Witherspoon in the holiday comedy "Four Christmases"
- 2007: Played the sarcastic, wild-at-heart younger brother of Santa Claus (Paul Giamatti) in the comedy "Fred Claus"
- 2007: Appeared with Emile Hirsch in Sean Penn's adaptation of the non-fiction book, "Into the Wild"
- 2006: Co-starred (also produced and co-wrote) with Jennifer Aniston in "The Break-Up"
- 2005: Co-starred with Owen Wilson in "Wedding Crashers" as friends who crash weddings to pick up women
- 2005: Traveled across the country performing his "Wild West Comedy Show"; show was subject of the documentary, "Wild West Comedy Show: 30 Days & 30 Nights - Hollywood to the Heartland" (released in 2008)
- 2005: Cast opposite Brad Pitt and Angelina Jolie in "Mr. and Mrs. Smith"
- 2004: Played a shady villain in the big screen adaption of the 1970's cop series "Starsky & Hutch"
- 2004: Starred opposite Ben Stiller in the comedy "Dodgeball: A True Underdog Story"
- 2003: Appeared as a man trying to recapture his frat house glory in the comedy "Old School"
- 2001: Played a mysterious stepfather who may or may not be involved in a murder in "Domestic Disturbance"
- 2001: Reteamed with Favreau to play a pair of low-level mobsters in "Made"; written and directed by Favreau
- 2000: Made guest appearance on an L.A.-set episode of HBO's comedy series "Sex and the City"
- 2000: Played an FBI agent in "The Cell" with Jennifer Lopez
- 1998: Reteamed with Phoenix in "Clay Pigeons"; played a seductive serial killer/con artist
- 1998: Portrayed Norman Bates in Gus Van Sant's shot-for-shot remake of "Psycho"; re-teamed with Anne Heche
- 1998: Starred opposite Anne Heche and Joaquin Phoenix in the drama "Return to Paradise"
- 1997: Cast by director Steven Spielberg in the sequel "The Lost World: Jurassic Park"
- 1997: Appeared opposite Kate Capshaw as a drifter who falls into romance with a widow in "The Locusts"
- 1996: Breakthrough screen role as Trent in "Swingers"; written by and co-starring Favreau
- 1996: Starred in the unsold UPN pilot for remake of "77 Sunset Strip"
- 1993: Film debut, "Rudy"; marked first collaboration with Jon Favreau
- 1992: Guest-starred as a patient on the ABC comedy, "Doogie Howser, M.D."
- 1990: Acted in three "CBS Schoolbreak Specials" playing high school students
- 1989: TV acting debut in the third-season premiere of "China Beach" (ABC)
- 1988: Appeared in TV commercial for Chevrolet's "Heartbeat of America" campaign
- Acted in children's theater
- Raised in the Oak Park-Lake Forest, Illinois, area
- Decided to pursue acting at age 17 after a car accident derailed any hopes of an athletic career
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