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For example, both auditioned for the same part in the 1990 TV series based on the 1989 comedy Parenthood.
Di Caprio was cast, and Maguire later got a guest role at least partly on Di Caprio's recommendation.
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.
He gained recognition for his role as Peter Parker/Spider-Man in Sam Raimi's Spider-Man trilogy.
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.
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.