Working as an child actor since his early teens, he worked in a variety of commercials and TV and movie roles, until he gained significant attention for with his role in the film, The Ice Storm, directed by Ang Lee. This soon was parlayed in a variety of lead roles where he played a thoughtful boy coming of age in a variety of films such as Pleasantville, The Cider House Rules and Wonder Boys.
In 2002, he shot to stardom in the title role in Spider-Man, where he was praised for his performance of the troubled superhero. He further solidified his stardom in 2003 with a leading role as the jockey, Jonathan "Red" Pollard, in an acclaimed film about the famous American racehorse, Seabiscuit.