- 2009: Played a Vietnam vet in Ang Lee's "Taking Woodstock"
- 2008: Played the lead role in the Wachowski brothers' live action film adaptation of the 1960s Japanese series "Speed Racer"
- 2008: Portrayed activist Cleve Jones in director Gus Van Sant's biopic "Milk"
- 2007: Portrayed the doomed idealist Christopher McCandless in Sean Penn's adaptation of the 1996 non-fiction book "Into the Wild"; earned a SAG nomination for Outstanding Male Actor in a Leading Role
- 2007: Cast as the infamous drug dealer Jesse James Hollywood, who became one of the youngest men ever on the FBI's most wanted list in Nick Cassavetes' "Alpha Dog"
- 2005: Portrayed Jay Adams in the Catherine Hardwicke directed "Lords of Dogtown"; a fictionalized take on a group of skateboarders that originated in Venice, CA during the 1970's
- 2004: Cast opposite Elisha Cuthbert in the comedy "The Girl Next Door"
- 2004: Starred with Sigourney Weaver and Jeff Daniels in the family drama "Imaginary Heroes"
- 2004: Starred as Duncan, a fourteen-year-old misfit farm boy trying to cope with his mother's death in "The Mudge Boy"
- 2002: Co-starred in the drama feature "The Emperor's Club"
- 2002: Made feature debut in "The Dangerous Lives Of Alter Boys"
- 1998: Cast as young Houdini in the made-for-television movie "Houdini"
- 1996: Made television debut on the series "Kindred: The Embraced"




