Worked as a production intern on "Bed & Breakfast"; produced by his father and starred his mother

Auditioned for the role of Tom Hanks' matchmaking son in "Sleepless In Seattle"; did not get the part

At age 14, formed band, Phantom Planet

Appeared in the music video for the rock remix of "It's All About the Benjamins" by Puff Daddy

Phantom Planet appeared as guests in an episode of the ABC sitcom "Sabrina, the Teenage Witch"

Feature film acting debut in leading role of Max Fischer in Wes Anderson's quirky comedy "Rushmore"

Co-starred in the comedy film "Slackers" (film originally set for release in 2000, but postponed to 2002)

Appeared in Roman Coppola's feature directing debut, "CQ"; screened out of competition at Cannes

Co-starred in Joe Pantoliano's directorial debut, "Just Like Mona"

Joined Dustin Hoffman and Lily Tomlin in David O. Russell's "I Heart Huckabee's"

Starred in the short-lived FOX comedy "Cracking Up"

Cast opposite Will Ferrell and Nicole Kidman in the big screen adaptation of "Bewitched"

Co-starred as struggling musician Jeremy in "Shopgirl," opposite Claire Danes and Steve Martin; adapted by Martin from his novella

Portrayed Louis XVI, opposite Kirsten Dunst, in Sofia Coppola's "Marie-Antoinette"

Formed the band, Coconut Records

Re-teamed with director Wes Anderson for the film, "The Darjeeling Limited"; also co-wrote with Anderson

Played egotistical actor, Mark Taylor Jackson in Judd Apatow's "Funny People"

Cast as writer Jonathan Ames, who moonlights as a private detective in the HBO drama series, "Bored to Death"