Milestones

- Will co-star with Kevin Bacon in Black Water Transit (lensed 2007)

- 2007 Starred in An American Crime, directed by Tommy O’Haver

- 2007 Once again reprised his role for Spider-Man 3, opposite Tobey Maguire and Kirsten Dunst

- 2007 Starred in lead role of Gregory Mackenzie’s Camille

- 2006 Starred opposite Brittany Murphy in the mystery drama The Dead Girl

- 2006 Starred opposite Rachel Miner in the short drama Grasshopper

- 2006 Directed and starred in Good Time Max

- 2006 Starred in Tony Bill’s Flyboys

- 2006 Starred opposite Salma Hayek in the gritty art drama Paint

- 2006 Starred opposite Jordana Brewster in the Disney drama Annapolis, directed by Justin Lin

- 2006 Starred in the period drama Tristan & Isolde

- 2006 Made directorial debut with The Ape originally co-wrote as a one-act play; released on DVD

- 2005 Co-starred with Benjamin Bratt in the WWII drama The Great Raid, the true story of the rescue of over
500 American prisoners-of-war from the notorious Cabanatuan Japanese POW camp

- 2004 Returned to co-star with Tobey Maguire and Kirsten Dunst in Spider-Man 2

- 2003 Played the love interest to Neve Campbell in The Company

- 2002 Co-starred with Tobey Maguire and Kirsten Dunst in Spider-Man

- 2002 Cast in lead role of Sonny, as a former gigolo whose family tries to lure him back to his old life

- 2002 Co-starred in the drama City By The Sea

- 2001 Portrayed the titular legend in the TNT biopic James Dean

- 2000 Starred as a popular jock in Whatever It Takes, a modern high school-set take on Edmond Rostand’s Cyrano de Bergerac

- 2000 Featured as a drug-addled musician in the VH1 original movie At Any Cost

- 1999 Was featured in the NBC miniseries To Serve and Protect

- 1999 Appeared in the feature teen comedy Never Been Kissed

- 1999 Guest starred on an episode of NBC’s FBI drama Profiler

- 1999 – 2000 Co-starred on the NBC series Freaks and Geeks, playing nihilistic Daniel

- 1998 Began to pursue an acting career following a 15-month intensive training course