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

Featured in the NBC miniseries "To Serve and Protect"

Appeared in the teen comedy "Never Been Kissed"

Cast on the short-lived but well-received NBC series "Freaks and Geeks"

First major film role, the romantic comedy, "Whatever It Takes"

Portrayed the titular legend in director Mark Rydell's biographical TV film, "James Dean" (TNT); nominated for an Emmy and a Screen Actors Guild Award

Cast in the supporting role of Harry Osborn, the son of the villainous Green Goblin, in director Sam Raimi's "Spider-Man"

Played Robert De Niro's son in the drama "City by the Sea"

Co-starred with Neve Campbell in Robert Altman's "The Company"

Reprised role of Harry Osborn for "Spider-Man 2"

Co-starred in the WWII drama "The Great Raid"

Portrayed legendary hero Tristan, opposite Sophia Myles in Tristan & Isolde"

Made directorial debut with "The Ape"; originally co-wrote as a one-act play and later released on video

Played the lead role in the WWI adventure "Flyboys"

Once again teamed with Tobey Mcguire and director Sam Raimi to play Harry Osborn for "Spider-Man 3"