Though he made his breakthrough as a neurotic comedy writer on "The Larry Sanders Show" (HBO, 1992-98),... (Learn more)
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| 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 | |
| Member of the Second City National Touring Company | |
| Raised in Evanston, IL | |
| 1986 | Feature acting debut, "Lucas" |
| 1987 | TV acting debut in an episode of "Jack and Mike" |
| 1989 - 1990 | Appeared as a regular in the variety series, "Carol & Company" (NBC) starring Carol Burnett |
| 1989 | First film with Cusack, "Say Anything" |
| 1992 | Appeared as a regular on HBO sitcom, "The Larry Sanders Show" |
| 1993 | First substantial film role, "Judgment Night" |
| 1993 | TV-movie debut, "12:01" (FOX) |
| 1994 | Had starring role in the feature comedy "PCU" |
| 1995 | Joined cast of the sitcom "Ellen" (ABC), playing the title character's cousin |
| 1997 | Once again teamed with Cusack on "Grosse Point Blank" |
| 1998 | Cast in featured role of a man who accidentally kills a prostitute during a bachelor party in "Very Bad Things" |
| 1998 | Played the title role in the ABC series "Cupid" |
| 2000 | Had supporting role in "Family Man" |
| 2001 | Hired to replace Frank Whaley in the FX black comedy series "Bad News, Mr. Swenson"; left project due to family issues |
| 2001 | Teamed on screen with John Cusack as best friends in "Serendipity" |
| 2003 | Cast as Dean Gordon Pritchard in Todd Phillips' comedy "Old School" also starring Luke Wilson, Will Ferrell and Vince Vaughn |
| 2003 | Once again teamed on screen with longtime friend John Cusack in "Runaway Jury," based on a John Grisham novel |
| 2004 - 0 | 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" |
| 2005 | Cast opposite Al Pacino in the sports gambling drama "Two for the Money" |
| 2006 | Cast as powered Hollywood agent throwing his son the ultimate Bar Mitzvah in the comedy "Keeping Up with the Steins" |
| 2007 | Cast in the Peter Berg directed, "The Kingdom" |
| 2007 | Co-starred in the action-comedy "Smokin' Aces" directed by Joe Carnahan |
| 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 |
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