Appeared in Q-Tip commercials from age eight months

First film appearance was as Robert De Niro's son in "Falling in Love"

TV-movie acting debut, "Classified Love"

TV-series acting debut in "The Rainmaker" episode of the anthology series, "Tribeca"

First leading role in a film, Steven Soderbergh's "King of the Hill"

Joined Jonny Lee Miller and Angelina Jolie in the film "Hackers"

Cast as Balthasar in Baz Luhrmann's adaptation of "William Shakespeare's Romeo + Juliet"

Played the adopted French son of an expatriate American writer in "A Soldier's Daughter Never Cries"

Co-starred in "Speedway Junky" (released theatrically in 2001)

Played the romantic interest in "Bring It On"

Starred in the sci-fi comedy "Clockstoppers"

Played the lead in the psychological thriller "Swimfan"

Co-starred in the black comedy "Eulogy"

Joined the ensemble drama feature "Heights"

Played a would-be young filmmaker in "Happy Endings"

Portrayed Rene Gagnon, one of the men who lifted the flag at the battle of Iwo Jima in Clint Eastwood's "Flags of Our Fathers"

Cast as a college buddy of Bush, in Oliver Stone's controversial biopic "W."