First professional stage role in the off-Broadway Horton Foote play, "Laura Dennis"

Made TV debut in an episode of NBC's "Law & Order"

Feature film debut in Tim Robbins' film "Dead Man Walking" playing one of the young murder victims

Appeared in the Drama Department's off-Broadway production of "Kingdom of Earth"

Featured in the "Underground" segment of HBO's anthology special "Subway Stories"

Portrayed John Malkovich's son and Leonardo DiCaprio's rival in "The Man in the Iron Mask"

Cast in Larry Clark's "Another Day in Paradise"

Played an institutionalized quadriplegic in the Showtime drama "Freak City"

Earned critical recognition for his breakthrough role as real-life killer John Lotter in "Boys Don't Cry"

Played the lead in Wayne Wang's erotic thriller, "Center of the World"

Cast as a meth addict in "The Salton Sea"

Co-starred with Elisabeth Shue in an off-Broadway revival of Lanford Wilson's "Burn This"

Offered a critically acclaimed performance as Hayden Christensen's editor in "Shattered Glass"; earned an Independent Spirit Award and Golden Globe nomination for Best Supporting Actor

Played the sarcastic best friend to Zach Braff's character in Braff's directorial debut "Garden State"

Cast as researcher Clyde Martin in "Kinsey" opposite Liam Neeson as Alfred Kinsey, a pioneer in the area of human sexuality research; received an Independent Spirit Award nomination for Best Supporting Male

Portrayed a bisexual screenwriter in "The Dying Gaul"

Played the local attorney, opposite Kate Hudson in the thriller "Skeleton Key"

Portrayed a marine in Sam Mendes' "Jarhead" based on former Marine Anthony Swofford's best-selling novel

Played an asexual activist opposite Molly Shannon in "Year of the Dog"

Co-starred with Reese Witherspoon in "Rendition"

Made Broadway debut in an adaptation of Anton Chekhov's "The Seagull" alongside Kristin Scott Thomas at the Royal Court Theatre

Co-starred with fiance Maggie Gyllenhaal in the Off-Broadway revival of Anton Chekhov's "Uncle Vanya"

Appeared in the film version of Michael Chabon's novel, "The Mysteries of Pittsburgh"