There are a lot of long time friendships in Hollywood, some stranger than others, but the friendship of Leonardo DiCaprio and Tobey Maguire is one of those friendships that have stood the test of time... and fame.
DiCaprio and Maguire's long time friendship is interesting to say the least, and has been constantly tested over it's 30 years. What really drew them together though, when they were just hitting the age of 12, was the fact that they had a similar background. They were both raised in Los Angeles in by single mothers, and both entered into the child acting scene in Hollywood in the 80s.
According to Esquire, DiCaprio saw Maguire filming on the streets of L.A. and recognized him from auditions. He immediately recognized himself in Maguire because it looked like he had the same determination to make it as a child star, just as DiCaprio was trying. When he spotted Maguire, DiCaprio told his mother to stop the car.
"I literally jumped out of the car," DiCaprio told Esquire. "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."
Their famous friendship started from that day, and from that day on they had each other's backs no matter what, even when DiCaprio beat Maguire for the leading role in This Boy's Life, which helped catapult DiCaprio into the spotlight. Maguire ended up getting a supporting role as one of DiCaprio's friends, just as the pairs real life friendship was growing.
After This Boy's Life, DiCaprio was cast in What's Eating Gilbert Grape, alongside Johnny Depp, and DiCaprio's fame skyrocketed just at the age of 19. But he was still just an ordinary guy, still trolling the streets of L.A. with Maguire and their other child star friends, Lukas Haas and Kevin Connolly, who would become Leonardo's "Pussy Posse".
While the "Pussy Posse" were still struggling with getting roles, DiCaprio became the biggest name in Hollywood for his roles as Romeo in Baz Luhrmann's Romeo + Juliet, and Jack in James Cameron's Titanic. But even as DiCaprio was struggling with this new-found fame, his friendship with Maguire and the "Pussy Posse" never changed.
In fact the parties just escalated for the infamous group, and they were dubbed the "Pussy Posse" because of their constant shenanigans with girls. DiCaprio even flew the gang to Australia with him when he was shooting Romeo + Juliet, so they could continue to chase girls. But more importantly they protected one another, and had each others backs, even when things got rough.
The group ended up making a black and white movie called Don's Plum, which was shot over six days in the summer of 1995 and late 1996. According to Vanity Fair that movie featured the group at the L.A. diner Don's Plum, where they go to meet up and talk about vulgar things, shout at girls, and revealing their own demons. After the film was done, DiCaprio and Maguire fought to have it not released in any American theater ever, and since then has become a sort of lost myth.
After the 90s came to a close, Maguire was cast in the Spider-Man franchise and went on to make a trilogy as the friendly neighborhood spider, while DiCaprio went on the make films like The Beach, Gang's of New York, and Catch Me If You Can. But their friendship became even more special when they finally got to star in the same movie, Luhrmann's The Great Gatsby, in 2013.
The Oklahoman reports, DiCaprio didn't have to go far to ask Maguire if he'd star in the F. Scott. Fitzgerald's adaptation, because they lived right next door from one another. "I happened to live next door to Leo at the time, so it wasn't a far journey," Maguire said. "I was like, 'Oh, yeah. Sure. I can be over in 30 seconds if that's good for you.'"
DiCaprio was once again the star of the film and Maguire the supporting role, and oddly enough they lived right next to each other in the film as well. The movie was a sort of metaphor for their relationship, but the pair didn't see it as that, they were just happy to finally be acting together, after working on Don's Plum years before.
"Every project we do, we talk about," DiCaprio told The Oklahoman. "Every single choice I've made, I've talked to Tobey about and vice versa. We've had endless conversations about certain projects and argued with one another and supported one another along the way."
Luhrmann saw the pairs potential as well. "I would have looked at Tobey anyway in the role of Nick Carraway because Tobey is exquisite with the still-waters-run-deep characterization," Luhrmann said. ''He and Leonardo's relationship really counted for something. We all knew that if we were going to go through this journey, it would be a plus that we were friends."
"I can't tell you how many countless times on set we would do a scene and come up to one another and say, 'What's your take on that? What was I doing, do you think?'" DiCaprio continued. "We had our own very distinct private conversations about everything."
Since staring in Gatsby together, DiCaprio has become a steady figure in Maguire's household, and is known as Uncle Leo to his kids. They support each other on and off-screen, hold parties for each other, hanging out, and even go to charity events with one another. They have respect for each other, and have essentially become brothers over the decades.
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