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June 14, 2022

The Ultimate Hollywood Bromance: Candid Photographs of Leonardo DiCaprio and Tobey Maguire in the 1980s

Celebrity friendships aren’t spoken about much these days, mostly because we don’t know who is considered a “friend,” especially with the romantic scandals and competition for roles out there. However, every now and then the red carpet will roll out a friendship we can’t get enough of. One of the longest-lasting Hollywood friendships is between none other than Leonardo DiCaprio and Tobey Maguire.

Both Tobey and Leo started their acting careers as child actors in the 1980s. One day, while Leo and his mother were driving through L.A., he recognized someone from a past audition. From that point on, the pair have been acting together, partying together, and supporting each other.

“I literally jumped out of the car,” DiCaprio recalled. “I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah — I know you. You’re… that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”

The pair worked together on This Boy’s Life, a second time for the indie flick Don’s Plum and were reunited for a big-screen adaptation of The Great Gatsby. A fourth collaboration, it goes without saying, is more than a certainty.


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