- 1995 – Gained early attention as the eccentric hacker Emmanuel Goldstein, known as Cereal Killer, in the cyber-thriller Hackers.
- 1996 – Broke into the mainstream with his energetic performance as Stu Macher in Wes Craven’s influential horror hit Scream.
- 1999 – Won Best Actor at the Mar del Plata International Film Festival for his leading performance as Stevo in the cult independent film SLC Punk!.
- 2002 – Entered a major family-film franchise by portraying Shaggy Rogers in the live-action Scooby-Doo, establishing one of his signature roles.
- 2009 – Succeeded Casey Kasem as the principal voice of Shaggy, extending the role into animated films, television series and games.
- 2011 – Took a notable dramatic turn as Brian Speer in Alexander Payne’s The Descendants; the cast subsequently received a Screen Actors Guild Award nomination for ensemble performance.
- 2012 – Made his feature-directing debut with Fat Kid Rules the World, which won the SXSW audience prize for the Narrative Spotlight section.
- 2023 – Returned prominently to theatrical horror as William Afton in Five Nights at Freddy’s, a hit that earned more than $291 million worldwide.
Milestones
