Joined the Second City National Touring Company
Acted as a child in his parents theater company The Piven Theatre Workshop
Made feature acting debut in "Lucas"
TV acting debut in an episode of "Jack and Mike"
Co-founder (with childhood pal John Cusack) of New Criminals theater group
First film with Cusack, "Say Anything"
Appeared as a regular in the variety series, "Carol & Company" (NBC) starring Carol Burnett
Appeared as a regular on HBO sitcom, "The Larry Sanders Show"
First substantial film role, "Judgment Night"
TV-movie debut, "12:01" (Fox)
Had starring role in the feature comedy "PCU"
Joined cast of the sitcom "Ellen" (ABC), playing the title character's cousin
Once again teamed with Cusack in "Grosse Point Blank"
Played the title role on the ABC series "Cupid"
Cast in featured role of a man who accidentally kills a prostitute during a bachelor party in "Very Bad Things"
Had supporting role in "Family Man"
Teamed on screen with John Cusack as best friends in "Serendipity"
Hired to replace Frank Whaley on the FX black comedy series "Bad News, Mr. Swenson"; left project due to family issues
Cast as Dean Gordon Pritchard in Todd Phillips' comedy "Old School," also starring Luke Wilson, Will Ferrell and Vince Vaughn
Once again teamed on screen with longtime friend John Cusack in "Runaway Jury," based on a John Grisham novel
Played a secret service agent in the comedy "Chasing Liberty"
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 opposite Al Pacino in the sports gambling drama "Two for the Money"
Cast as powered Hollywood agent throwing his son the ultimate Bar Mitzvah in the comedy "Keeping Up with the Steins"
Co-starred in the action-comedy "Smokin' Aces" directed by Joe Carnahan
Cast in the Peter Berg directed "The Kingdom"
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 a used-car liquidator in "The Goods: Live Hard, Sell Hard"
Co-starred in Mark Pellington's "I Melt with You"
Voiced Black Bellamy in the animated adventure "Pirates! Band of Misfits"