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Tobey Maguire's Most Memorable Film Roles

By Carol Cassada

Tobey Maguire went from a child star to one of Hollywood's most popular actors. Throughout his nearly 30-year acting career, Maguire has shown his acting chops as he's played comedic, dramatic, and action roles.

Maguire had big shoes to fill when he signed on to play Spiderman in the 2002 Sam Raimi film. But Maguire proved critics wrong with his amazing portrayal of the superhero.

Maguire has earned praise and award nominations for his work. Even though he may not be in the spotlight much these days, he's provided us with plenty of memorable film roles over the years.

Let's take a look at a few of his roles.

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Spiderman is no doubt Maguire's most famous role. Director Sam Raimi hired Tobey to play the iconic superhero for his 2002 film. Maguire was the perfect choice to play nerdy Peter Parker, who suddenly finds himself transformed into a superhero thanks to a bite from a spider.

Maguire shined in his role and earned countless praise from movie critics and comic book fans. Maguire would reprise the role for two more sequels before hanging up the Spiderman suit in 2007.

While there have been plenty of other actors to play Spiderman over the years, nobody can beat Tobey Maguire's performance.

The Cider House Rules

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Maguire can a chance to showcase his versatile acting in the 1999 film The Cider House Rules. Starring alongside legendary actor Michael Caine and newcomer Charlize Theron, Maguire won the hearts of movie goers with his performance as Homer Wells.

Throughout the film, Maguire's character goes from being raised in an orphanage by Caine to embarking a new life with Theron. The film was a box-office hit and earned critical acclaim as well. It also helps establish Maguire as one of Hollywood's newest leading men.


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Maguire got a chance to showcase his comedy skills in the 1998 film Pleasantville. In the movie, Maguire and his sister, played by Reese Witherspoon find themselves mysteriously transported into a television series called Pleasantville.

Magure and Witherspoon adjust to living a new life in the black and white sitcom, where everybody seems happy. But as the movie progresses, we see that not everything is pleasant in Pleasantville.

Even though the movie wasn't a box-office hit, critics enjoyed it. Maguire's performance earned him a Saturn Award nomination for Best Performance by a Younger Actor.

The Great Gatsby

In one of his most recent roles, Maguire signed on to play Nick Carraway in the 2013 remake of The Great Gatsby.

Maguire starred alongside his good friend Leonardo DiCaprio, who played the title role of Jay Gatsby. This would be the second time the actors worked together, their first movie was the 1993 film This Boy's Life.

Baz Luhrmann's remake of The Great Gatsby was filled with lots of glitz and glamour. Even though critics panned the film, it did go on to earn over $300 million at the box office.

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