Maguire's distinction as one of his generation's best actors was solidified with leading parts in Pleasantville (1998), The Cider House Rules (1999) and Wonder Boys (2000). But it was his performances in Spider-Man (2002) and Spider-Man 2 (2004) that catapulted him to A-list status.
In 2003, Maguire took a break from playing a superhero to portray jockey Red Pollard in Seabiscuit (opposite Jeff Bridges and Chris Cooper). The talented actor racked up a 2009 Golden Globe nod as Best Actor for his role in Brothers.