Took drama as a school elective as a sixth grader

Began studying acting at the suggestion of neighbor, who was an entertainment manager

Made TV debut in an ad for Doritos

First acting role was a small part in the HBO special, "On Location: Rodney Dangerfield 'Opening Night at Rodney's Place'" (aired in May 1989)

Starred in the Nickelodeon special, "Tales From the Whoop: Hot Rod Brown, Class Clown"

Met longtime friend Leonardo DiCaprio when they auditioned for a role on NBC's "Parenthood"; DiCaprio got the part, but Maguire got a guest role due to DiCaprio's recommendation

Played leading role in short-lived FOX sitcom, "Great Scott!"

Made feature film debut with a small role in "This Boy's Life" starring Leonardo DiCaprio

First film lead in the horror feature, "Revenge of the Red Baron"

Filmed a small part in "Empire Records"; Maguire later requested director Allan Moyle release him from his part in the movie due to health reasons; Moyle agreed and all of Tobey's scenes were deleted

Appeared with DiCaprio in "Don's Plum"; with DiCaprio filed a 1998 lawsuit to halt distribution of film, claiming it was originally intended to be a short and not a full-length film; settled with producers for a reported $10 million and a guarantee the film would not be released in the US or Canada

Co-starred with Kate Capshaw in Griffin Dunne's Oscar-nominated short, "The Duke of Groove"

Cast in the NBC true crime TV-movie, "Seduced by Madness: The Diana Borchardt Story"

Played a leading role in the independent feature, "Joyride"

Played the son of Kevin Kline and Joan Allen in Ang Lee's "The Ice Storm"; also narrated

Played one of the alter egos of Woody Allen's novelist Harry Block in "Deconstructing Harry"

Co-starred with Reese Witherspoon in Gary Ross' "Pleasantville"; second collaboration with Joan Allen playing his mother

Re-teamed with director Ang Lee for the American Civil War drama, "Ride With the Devil"

Played the film's protagonist, Homer Wells in Lasse Hallstrom's film adaptation of John Irving's novel, "The Cider House Rules"

Teamed with Michael Douglas for Curtis Hanson's "Wonder Boys"; adapted from Michael Chabon's novel

Played the title role in Sam Raimi's feature adaptation of the popular comic book, "Spider-Man"

Made debut as a producer with "The 25th Hour"

Re-teamed with Gary Ross to play jockey Red Pollard in the acclaimed film, "Seabiscuit"; also executive produced

Reprised his role in the blockbuster, "Spider-Man 2"

Co-starred with George Clooney and Cate Blanchett in "The Good German"; directed by Steven Soderbergh

Once again collaborated with director Sam Raimi for "Spider-Man 3"