Landed a featured role in "Spy Kids: All the Time in the World in 4D"
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"
Acted as a child in his parents theater company The Piven Theatre Workshop
Cast as Dean Gordon Pritchard in Todd Phillips' comedy "Old School," also starring Luke Wilson, Will Ferrell and Vince Vaughn
First substantial film role, "Judgment Night"
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
Teamed on screen with John Cusack as best friends in "Serendipity"
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
Made feature acting debut in "Lucas"
First film with Cusack, "Say Anything"
Had starring role in the feature comedy "PCU"
Joined cast of the sitcom "Ellen" (ABC), playing the title character's cousin
Joined the Second City National Touring Company
Once again teamed with Cusack in "Grosse Point Blank"
Played a secret service agent in the comedy "Chasing Liberty"
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; earned Golden Globe (2004, 2005, 2006, 2007, 2009), Emmy (2005) and SAG (2007, 2008, 2009) nominations for Supporting and Lead Actor in a Comedy Series
Cast in featured role of a man who accidentally kills a prostitute during a bachelor party in "Very Bad Things"
Cast in the Peter Berg directed "The Kingdom"
Co-founder (with childhood pal John Cusack) of New Criminals theater group
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
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"