Cast as powered Hollywood agent throwing his son the ultimate Bar Mitzvah in the comedy "Keeping Up with the Steins"
Cast opposite Al Pacino in the sports gambling drama "Two for the Money"
Played a used-car liquidator in "The Goods: Live Hard, Sell Hard"
Cast as Dean Gordon Pritchard in Todd Phillips' comedy "Old School," also starring Luke Wilson, Will Ferrell and Vince Vaughn
Had supporting role in "Family Man"
Hired to replace Frank Whaley on the FX black comedy series "Bad News, Mr. Swenson"; left project due to family issues
Once again teamed on screen with longtime friend John Cusack in "Runaway Jury," based on a John Grisham novel
Appeared as a regular in the variety series, "Carol & Company" (NBC) starring Carol Burnett
Co-starred in the action-comedy "Smokin' Aces" directed by Joe Carnahan
Had starring role in the feature comedy "PCU"
Cast in the Peter Berg directed "The Kingdom"
Played the title role on the ABC series "Cupid"
TV-movie debut, "12:01" (Fox)
Co-starred in Mark Pellington's "I Melt with You"
Voiced Black Bellamy in the animated adventure "Pirates! Band of Misfits"
Appeared in the ensemble neo-noir sequel "Sin City: A Dame to Kill For"
Had first substantial film role in "Judgment Night"
Teamed on screen with John Cusack as best friends in "Serendipity"
Made his feature acting debut in "Lucas"
Made his first film with childhood pal John Cusack, "Say Anything"
Joined cast of the sitcom "Ellen" (ABC), playing the title character's cousin
Once again teamed with Cusack in "Grosse Point Blank"
Played a secret service agent in the comedy "Chasing Liberty"
Made his TV acting debut in an episode of "Jack and Mike"
Appeared as a regular on HBO sitcom, "The Larry Sanders Show"
Cast as Ari, the ruthless high-power agent on the HBO series "Entourage," produced by Mark Wahlberg
Cast in featured role of a man who accidentally kills a prostitute during a bachelor party in "Very Bad Things"
Made Broadway debut in a NYC production of David Mamet's "Speed-the-Plow"; ended his run early due to a condition caused by a high mercury count
Landed a featured role in "Spy Kids: All the Time in the World in 4D"
Had an uncredited role in Doug Liman's blockbuster sci-fi actioner "Edge of Tomorrow"
Had the starring role on the drama "Mr Selfridge"
Began co-starring on the police procedural "Wisdom of the Crowd"
Appeared in the TV documentary "Jeremy Piven's Journey of a Lifetime"