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Milestones
- 2004: Starred in "P.S." with Laura Linney and Topher Grace
- 2004: Portrayed journalist Brian Fantana in the comedy "Anchorman" with Will Ferrell
- 2003: Revised role of Adam in the feature film adaptation of Neil LaBute's "The Shape of Things"
- 2003: Starred in "House Hunting" with Zooey Deschanel and Felicity Huffman; written and
directed by Amy Lippman
- 2001: Portrayed Nick Carraway in the A&E adaptation of "The Great Gatsby"
- 2001: Acted in the London stage production of "The Shape of Things", written and directed by Neil LaBute
- 2000: Made London stage debut playing Jamie Tyrone in "Long Day's Journey Into Night", starring Charles Dance and Jessica Lange
- 2000: Starred opposite Andie MacDowell in the short "Reaching Normal", written and directed by Anne Heche; screened at Sundance before airing on Showtime
- 1999: Co-starred as WWII pilot Wally Worthington in "The Cider House Rules"
- 1999: Returned to the stage to co-star with Calista Flockhart in "Bash", delivering a chilling monologue as a Mormon college student who participated in a brutal attack on a gay couple; reprised role in Los Angeles
- 1999: Appeared opposite Courtney Love as a recently jilted guy depressed over his love life in the indie romantic comedy "200 Cigarettes"
- 1998: First leading role in a mainstream feature, cast as a gay schoolteacher who befriends an unwed pregnant woman in "The Object of My Affection", directed by Nicholas Hytner
- 1998: Returned to the Broadway stage as Orsino to Helen Hunt's Viola in "Twelfth Night", staged by Hytner; production aired on PBS' "Live From Lincoln Center" under the direction of Kirk Browning on August 30
- 1997: Made Broadway stage debut in Alfred Uhry's "The Last Night of Ballyhoo"
- 1997: Reteamed with Ashley Judd in "The Locusts"
- 1996: Made guest appearance on TV sitcom "Clueless" (ABC) as date of Cher (played by Rachel Blanchard)
- 1996: Portrayed glibly preppy Dave Paris in Baz Lurhmann's "William Shakespeare's Romeo and Juliet"
- 1995: Breakthrough screen role in "Clueless", playing Josh, the stepbrother of Alicia Silverstone's Cher
- 1995: Feature film debut, "Halloween: The Curse of Michael Myers"; filmed before "Clueless" but released after
- 1994: Co-starred on short-lived Fox sitcom "Wild Oats"
- 1993: TV miniseries debut, "The Fire Next Time" (CBS)
- From 1992 to 1995: TV acting debut in recurring role as Kirby Philby, the husband of Reed Halsey (originated by Ashley Judd and then played by Noelle Parker) in the NBC series "Sisters"
- Raised in Kansas City, Missouri
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