- 2009: Played a used-car liquidator in "The Goods: Live Hard, Sell Hard"
- 2008: 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
- 2007: Co-starred in the action-comedy "Smokin' Aces" directed by Joe Carnahan
- 2007: Cast in the Peter Berg directed, "The Kingdom"
- 2006: Cast as powered Hollywood agent throwing his son the ultimate Bar Mitzvah in the comedy "Keeping Up with the Steins"
- 2005: Cast opposite Al Pacino in the sports gambling drama "Two for the Money"
- 2004: Cast as Ari, the ruthless high power agent on the HBO series "Entourage," produced by Mark Wahlberg; earned Golden Globe (2005, 2006, 2007, 2009), Emmy (2005) and SAG (2007, 2008, 2009) nominations for Supporting and Lead Actor in a Comedy Series
- 2004: Played a secret service agent in the comedy "Chasing Liberty"
- 2003: Once again teamed on screen with longtime friend John Cusack in "Runaway Jury," based on a John Grisham novel
- 2003: Cast as Dean Gordon Pritchard in Todd Phillips' comedy "Old School" also starring Luke Wilson, Will Ferrell and Vince Vaughn
- 2001: Teamed on screen with John Cusack as best friends in "Serendipity"
- 2001: Hired to replace Frank Whaley in the FX black comedy series "Bad News, Mr. Swenson"; left project due to family issues
- 2000: Had supporting role in "Family Man"
- 1998: Played the title role in the ABC series "Cupid"
- 1998: Cast in featured role of a man who accidentally kills a prostitute during a bachelor party in "Very Bad Things"
- 1997: Once again teamed with Cusack on "Grosse Point Blank"
- 1995: Joined cast of the sitcom "Ellen" (ABC), playing the title character's cousin
- 1994: Had starring role in the feature comedy "PCU"
- 1993: TV-movie debut, "12:01" (FOX)
- 1993: First substantial film role, "Judgment Night"
- 1992: Appeared as a regular on HBO sitcom, "The Larry Sanders Show"
- 1989: First film with Cusack, "Say Anything"
- 1989: Appeared as a regular in the variety series, "Carol & Company" (NBC) starring Carol Burnett
- 1987: TV acting debut in an episode of "Jack and Mike"
- 1986: Feature acting debut, "Lucas"
- Member of the Second City National Touring Company
- Raised in Evanston, IL
- Acted as a child in his parents theater company, The Piven Theatre Workshop
- Co-founder (with childhood pal John Cusack) of New Criminals theater group




