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The lifelong friendship of Tobey Maguire and Leonardo DiCaprio

Due to the fact that they were both child actors when they met, Leonardo DiCaprio and Tobey Maguire were destined to be best friends. “I literally jumped out of the car,” DiCaprio recalled in 2014. “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.”

It’s not the most auspicious of starts, but actors DiCaprio and Maguire have been friends for a very long time. 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.

But what’s more interesting than their collaboration is the friendship, or “bromance”, the pair enjoy. The 1990s was an exciting time to be young, and DiCaprio, the star of Titanic, was exposed to some of the steamier sides of the decade. Luckily, he had a firm friend base with Maguire, Lukas Haas, and Kevin Connolly, all burgeoning actors and revelling in burgeoning fame.

“A little competition rose up between them,” an anonymous actor told Nancy Jo Sales. “They were always betting on who would blow up first.” DiCaprio and Maguire could occasionally be spotted at Victoria’s Secret events in New York City, or on impromptu visits to American playground, Las Vegas. Due to their constant partying, DiCaprio’s troupe was known as the ‘Pussy Posse’ by others within the Hollywood circle. High profile was an unavoidable factor for the blue-eyed boys of mainstream cinema.

The term wasn’t an endearing one, but for DiCaprio, it was a network he could depend on in times of struggle. “I really like to have sweet people around me,” DiCaprio admitted to Detour magazine in 1996. “I can’t stand badasses. There’s too many of them, especially at my age in L.A. and…you have to peel away so many layers of those people.”

Invariably, DiCaprio was the most recognised of the posse, largely due to his stature as a heart-throb. “The Titanic stuff has caused this big identity crisis,” the anonymous actor told Sales. “Some of them have completely lost their careers. All they do now is hang out with Leo.”

Women threw themselves at DiCaprio, and his friends were happy to be in and around the party. It’s to his credit that DiCaprio recognised that this would have a damaging effect on his career, and he and Maguire blocked Don’s Plum from being released in America. They claimed that they had never agreed to a feature, and said they had signed on for a short. But I suspect the film’s dim treatment of women was not something they wanted to be associated with. In one revealing moment, DiCaprio is allegedly caught saying: “Stop looking at me like that—I’ll fucking throw a bottle at your face, you goddamn whore.” Maguire laughs in encouragement.

By the turn of the millennium, Maguire, now cast as Spider-Man, was now in a committed relationship, so he probably didn’t want to be reminded of his “bachelor” days with the Pussy Posse. When he isn’t acting, he’s a father.

As of the time of this article, DiCaprio remains unmarried, although he has been romantically linked to a number of women, many of them younger than him. But he’s remained friends with Maguire. Both of them were linked to Molly Bloom’s high stakes poker tournament in the mid-2000s at The Viper Room. Maguire is said to have influenced Michael Cera’s character in the 2017 film adaptation, Molly’s Game.

Considering his more mellow approach to life, some might think it’s unwise of the Spider-Man star to hang out with an actor who seems to make it his mission not to grow up. Even Ricky Gervais called DiCaprio out with one of his jokes when he said: “Leo DiCaprio attended the premiere and by the end, his date was too old for him,” the comedian said. DiCaprio, caught on camera, laughed nonchalantly. Clearly, he’s heard it before, and it doesn’t bother him.

But like DiCaprio, Maguire isn’t worried about what anyone might think of him. “We’re both really competitive people,” Maguire told The Guardian. “I think we have a lot of confidence in our own individual paths, so whether it’s with each other, or other friends of ours, we root for them. We’re fans of our greatest competitors. We can joke with each other about competition, but are supportive. I have a whole bunch of friends like that. I’m glad that’s the culture of my group.”

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