- 2007: Once again collaborated with director Sam Raimi for "Spider-Man 3"
- 2006: Co-starred with George Clooney and Cate Blanchett in "The Good German"; directed by Steven Soderbergh
- 2004: Reprised his role in the blockbuster, "Spider-Man 2"
- 2003: Re-teamed with Gary Ross to play jockey Red Pollard in the acclaimed film, "Seabiscuit"; also executive produced
- 2002: Made debut as a producer with "The 25th Hour"
- 2002: Played the title role in Sam Raimi's feature adaptation of the popular comic book, "Spider-Man"
- 2000: Teamed with Michael Douglas for Curtis Hanson's "Wonder Boys"; adapted from Michael Chabon's novel
- 1999: Played the film's protagonist, Homer Wells in Lasse Hallstrom's film adaptation of John Irving's novel, "The Cider House Rules"
- 1999: Re-teamed with director Ang Lee for the American Civil War drama, "Ride With the Devil"
- 1998: Co-starred with Reese Witherspoon in Gary Ross' "Pleasantville"; second collaboration with Joan Allen playing his mother
- 1997: Played a leading role in the independent feature, "Joyride"
- 1997: Played one of the alter egos of Woody Allen's novelist Harry Block in "Deconstructing Harry"
- 1997: Played the son of Kevin Kline and Joan Allen in Ang Lee's "The Ice Storm"; also narrated
- 1996: Cast in the NBC true crime TV-movie, "Seduced by Madness: The Diana Borchardt Story"
- 1995: 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
- 1995: Co-starred with Kate Capshaw in Griffin Dunne's Oscar-nominated short, "The Duke of Groove"
- 1995: 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
- 1994: First film lead in the horror feature, "Revenge of the Red Baron"
- 1993: Made feature film debut with a small role in "This Boy's Life" starring Leonardo DiCaprio
- 1992: Played leading role in short-lived FOX sitcom, "Great Scott!"
- 1990: 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
- 1990: Starred in the Nickelodeon special, "Tales From the Whoop: Hot Rod Brown, Class Clown"
- 1988: 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)
- 1987: Began studying acting at the suggestion of neighbor, who was an entertainment manager
- Made TV debut in an ad for Doritos
- Took drama as a school elective as a sixth grader




