- 2009: Co-starred with Jason Segel in the comedy, "I Love You, Man"
- 2009: Voiced Reese Witherspoon's fiancé in the computer-animated 3-D feature, "Monsters vs. Aliens"
- 2008: Played a supporting role in the Apatow produced, "Forgetting Sarah Marshall"
- 2008: Co-wrote (with David Wain) the comedy feature "Role Models"; also co-starred with Seann William Scott
- 2007: Starred as Katherine Heigl's brother-in-law in the Judd Apatow directed "Knocked Up"
- 2006: Joined Bradley Cooper and Julia Roberts in the Broadway production of Richard Greenberg's "Three Days of Rain"
- 2005: Cast as Steve Carell's buddy in Judd Apatow's "The 40 Year-Old Virgin"
- 2004: Portrayed journalist Brian Fantana in the comedy "Anchorman" with Will Ferrell
- 2003: Reprised role of Adam in the 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
- 2002: Played the recurring role of Mike Hannigan, the boyfriend and later husband of Lisa Kudrow's Phoebe Buffay, in "Friends" (NBC)
- 2001: Played Adam in Neil LaBute's London stage production of "The Shape of Things"
- 2001: Portrayed Nick Carraway in the A&E adaptation of "The Great Gatsby"
- 2000: Made London stage debut playing Jamie Tyrone in "Long Day's Journey Into Night"
- 2000: Starred opposite Andie MacDowell in the short "Reaching Normal"; written and directed by Anne Heche; screened at Sundance before airing on Showtime
- 1999: Appeared as a recently jilted guy depressed over his love life in the indie comedy "200 Cigarettes"
- 1999: Co-starred as WWII pilot Wally Worthington in "The Cider House Rules"
- 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"; production aired on PBS' "Live From Lincoln Center" under the direction of Kirk Browning (August 30)
- 1997: Reteamed with Ashley Judd in "The Locusts"
- 1997: Made Broadway stage debut in Alfred Uhry's "The Last Night of Ballyhoo"
- 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" as 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)
- 1992: TV acting debut 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 Overland Park, KS




