By age eight, started auditioning for various Chicago theaters; hired by Goodman Theater to appear in Tennessee Williams' "House Not Meant to Stand" and opposite Brian Dennehy in "Galileo"
Acted with Chicago's Absolute Theater Company and at the Cherry Street Theater
Made film debut as Kevin Kline's son in Lawrence Kasdan's "Grand Canyon"
TV debut, opposite Reese Witherspoon in "Desperate Choices: To Save My Child" (NBC)
Moved to Los Angeles and landed the role of Andrew, an epileptic and retarded teenager in "The Care and Custody of Barbara Moon" at Theatre Geo
Starred as a sexually confused, vulnerable and explosive young man in the independent feature "The Crew"
Appeared in Disney's ABC-TV remake of "The Shaggy Dog" as Trey Miller, the hero's cool best friend who invisions himself a teenage Casanova
Played a serial killer in "Hideaway"; first film with Alicia Silverstone
Re-teamed with Alicia Silverstone, playing popular and rich high school student Elton in "Clueless"
Portrayed Gwyneth Paltrow's love interest in "Moonlight and Valentino"
Co-starred in in the ensemble of "White Squall"; directed by Ridley Scott
Acted in the black comedy-thriller "Suicide Kings" as a morphine-addicted medical student
Played distance runner Frank Shorter to Billy Crudup's Steve Prefontaine in "Without Limits"
Featured in the ensemble of the festival-screened "Bongwater," playing Andy Dick's comic love partner
Portrayed Frederick Seward in "The Day Lincoln Was Shot" (TNT)
Starred as a young Hollywood screenwriter who deals with the untimely death of his wife in "This Space Between Us"
Played the over-the-edge radical Kenny Klein in NBC's miniseries "The '60s"
Played the title role in the CBS miniseries "Jesus"
Cast as Jennifer Lopez's troubled brother in "Angel Eyes"
Cast in the award winning HBO series "Six Feet Under" as Billy Chenowith, the troubled brother of Rachel Griffith's character Brenda
Played title role in the TNT miniseries "Julius Caesar"
Co-starred in the indie thriller "Wrong Turn"
Cast opposite Ashton Kutcher and Amanda Peet in the romantic comedy "A Lot Like Love"
Starred alongside Larry Bryggman, Ali MacGraw and Julianna Margulies in the Broadway production of "Festen"
Cast as a hostage rescue specialist in the NBC drama "Kidnapped"
Played a heroin addict opposite Heather Graham in the indie film "Broken"
Co-starred with Keri Russell in the indie feature "Waitress"; helmed by Adrienne Shelly, who was murdered before the film's release
Joined the cast of NBC's "Law & Order" as a detective; series was cancelled after being on the air for 20 years
Co-starred as the father of a Manhattan teen (Jane Levy) who moves from the big city to the suburbs on the ABC comedy series "Suburgatory"