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He reprised the role in the sequels Spider-Man 2 (2004) and Spider-Man 3 (2007), and has also provided the voice of Spider-Man for the video game adaptations of the films.All three movies went on to be part of the highest-grossing movies each year.Maguire changed his career path slightly to obtain roles where he and Di Caprio would not always be in competition for the same part, and the move paid off when given the role of Paul Hood, a teenage boarding school student whose narration anchors the action, in Ang Lee's 1997 film, The Ice Storm.

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In 1995, he requested director Allan Moyle to release him from his part in the movie Empire Records.

Moyle agreed, and all of Maguire's scenes were deleted from the final film.

The transient nature of his school years began to take a toll on Maguire emotionally, and after another relocation for his freshman year, he dropped out of high school and did not return. Maguire's first appearance in a feature film was in 1989's The Wizard.

He plays one of Lucas Barton's goons (one of three competitors at a video game competition) and had no lines.

Eventually, he was cast as the lead in the FOX TV series Great Scott! During many of his auditions, Maguire found himself auditioning for roles opposite another rising actor, Leonardo Di Caprio.

The pair quickly became friends and made an informal pact to help each other get parts in their movies/TV shows/other projects.

In Ride with the Devil (1999), Maguire portrayed Jakob Roedel, opposite Jewel Kilcher.

Here he played the son of a unionist German immigrant who joins his southern friends in the Missouri riders, avenging the atrocities committed against Missourians by Kansas Jayhawkers and redleggers.

Maguire and Di Caprio once again performed together, in Baz Luhrmann's remake of The Great Gatsby (2013); Di Caprio played the title role, while Maguire played the story's narrator, Nick Carraway. That same year he also established his own production company, Material Pictures, which secured independent financing in 2013 to help it produce more feature films.

His next film, Pawn Sacrifice (2015), was also co-produced by Material Pictures.

Near the end of Tropic Thunder, it is revealed that Maguire's character has been nominated for a Best Actor Oscar for Satan's Alley, which he loses to Tugg Speedman (Ben Stiller) for his role in Tropic Blunder, presented by Kirk Lazarus.

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