It’s well-documented that Tobey Maguire and Leonardo DiCaprio are good pals. For a time, the duo were part of an illicit partying collective, the poorly named ‘Pussy Posse’, which also featured the likes of Lukas Haas, Kevin Connolly, Harmony Korine, Ethan Suplee and David Blaine.
The first time that Leo laid eyes on Maguire actually came on the streets, a time when he spotted Maguire walking down the road as he rode in the back of his mother’s car. Leo once explained: “I literally jumped out of the car. 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.”
DiCaprio, Maguire and the rest of the posse used to tear around New York City, causing all manner of trouble. An anonymous film director once explained: “New York is like Leo’s playground, his Disneyland. They used to set off stink bombs at Sky Bar. But Leo’s not going to act up out here now. Anyone in the, of course, movie industry could be sitting at the next table. [But] no one in the industry cares what he does in New York.”
However, despite the clear wild nights of debauchery that DiCaprio and Maguire used to get up to, Leo felt that Maguire was a sweet man deserving of his friendship. He once said of his friends: “I really like to have sweet people around me. I can’t stand badasses. There’s too many of them, especially at my age in LA, and you have to peel away so many layers of those people.”
Although both Leo and Maguire came up in Hollywood around the same time and were, therefore, most likely auditioning for the same roles, this never prevented them from striking up a lasting bond and friendship. The duo performed together in 2013’s adaptation of The Great Gatsby, with Leo taking on the titular role while Maguire played his best buddy, Nick Carraway.
So too, did the pair perform together in the unreleased Don’s Plum, an utterly misogynistic picture in which Maguire was said to have a monologue explaining the joys of anal masturbation. However, both actors noted the damaging effect the film was likely to have on their reputations, and, as such, it was thankfully banned.
Maguire has also gone on record to speak glowingly of his friendship with DiCaprio and noted that they did not really care what others thought of their escapades. He said: “We’re both really competitive people. 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.”
