Movie Talk

Leonardo DiCaprio and Tobey Maguire: A Bromance of 25 Years

Movie Talk

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Leonardo DiCaprio and Tobey Maguire in 'The Great Gatsby' (Warner Bros.)


Despite his many ex-girlfriends, Leonardo DiCaprio really can maintain a long-term relationship. He and his "The Great Gatsby" co-star, Tobey Maguire, have been good friends for nearly 25 years.

What is undoubtedly one of Hollywood's longest-running and most notorious bromances began in their teens while they were auditioning for the same roles in the late-1980s. As the fable goes, the pair quickly became friends and vowed to help each other get parts. That began with the short-lived television comedy "Parenthood," when DiCaprio scored a major role and urged producers to bring Maguire on as a guest star, and continues today with this weekend's big release.

When asked if they could imagine playing the roles of Nick Carraway and Jay Gatsby with other actors, Maguire told Yahoo! Movies, "I can't," while DiCaprio described the casting choice as "very natural."

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"Venturing into a film of this magnitude and trying to adapt such a respected, celebrated novel like 'The Great Gatsby' wouldn't have been easy if I didn't have a trusted ally like Tobey," DiCaprio, 38, told us. "I don't know if I would've as easily dove into this experience if it weren't for him."

"We were kind of collaborators, trusting partners the whole way through in regards to making this movie together," Maguire, 37, explained. "I also think the timing and his position and his abilities as an actor uniquely qualify him for this part right now, and I had a blast doing it with him."

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Maguire and DiCaprio in Hollywood in 1991 (Vincent Zuffante/Star File)

Through the years, the two BFFs have been notorious for having "a blast" together. In the '90s, they formed "The P---- Posse" with several of their co-stars, including Lukas Haas, David Blaine, and Kevin Connolly, and they notoriously partied together, club-hopping and chasing girls. (Of course, DiCaprio disavowed this reputation and his crew's name, telling Rolling Stone in 2000 that he certainly didn't come up with the moniker, adding, "I think it’s the most degrading thing toward women I’ve ever heard in my life.")

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"Gatsby" isn't the pals' first time in a movie together. They shared just a few moments of screen time in "This Boy's Life" in 1993 and co-starred in 1995's "Don's Plum," about Los Angeles teens hanging out at a local diner.

Even though Maguire is married with two kids now, the gents still make time for a little banter … and a little game of hoops.

"We are like any other buddies," Maguire told People. "There's a lot of laughing and chatting between us. We enjoy doing a lot of things we have in common, like basketball. We like to play and talk about basketball."

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