- 2008: Nominated for the 2008 Golden Globe Award for Best Performance by an Actor in a Motion Picture – Musical or Comedy ("Pineapple Express")
- 2008: Portrayed Harvey Milk's (played by Sean Penn) lover in director Gus Van Sant's biopic "Milk"
- 2008: Co-starred with Seth Rogen in "Pineapple Express"; co-wrote and co-produced by Rogen and Judd Apatow
- 2008: Nominated for the 2008 Independent Spirit Award for Best Supporting Male (“Milk”)
- 2007: Once again teamed with Tobey Mcguire and director Sam Raimi to play Harry Osborn for "Spider-Man 3"
- 2007: Made a cameo appearance in Judd Apatow's "Knocked Up"
- 2006: Made directorial debut with "The Ape"; originally co-wrote as a one-act play and later released on video
- 2006: Played the lead role in the WWI adventure "Flyboys"
- 2006: Portrayed legendary hero Tristan, opposite Sophia Myles in Tristan & Isolde"
- 2005: Co-starred in the WWII drama "The Great Raid"
- 2004: Reprised role of Harry Osborn for "Spider-Man 2"
- 2003: Co-starred with Neve Campbell in Robert Altman's "The Company"
- 2002: Played Robert De Niro's son in the drama "City by the Sea"
- 2002: Cast in the supporting role of Harry Osborn, the son of the villainous Green Goblin, in director Sam Raimi's "Spider-Man"
- 2001: Portrayed the titular legend in director Mark Rydell's biographical TV-movie "James Dean" (TNT); earned Emmy and SAG nominations for Lead Actor in a TV-movie
- 2000: First major film role, the romantic comedy, "Whatever It Takes"
- 1999: Appeared in the teen comedy "Never Been Kissed"
- 1999: Featured in the NBC miniseries "To Serve and Protect"
- 1999: Cast on the short-lived, but well-received NBC series "Freaks and Geeks"; produced by Judd Apatow
- 1998: Began to pursue an acting career following a 15-month intensive training course




