Inside Leonardo DiCaprio and Tobey Maguire’s epic bromance: from meeting as kids in Hollywood and starring in The Great Gatsby together, to partying on yachts with models Neelam Gill and Rose Bertram

Aug 25 , 2023

Hollywood A-listers Leonardo DiCaprio and Tobey Maguire are long-time friends. Photo: Getty Images

DiCaprio and Maguire have a long-time friendship that extends nearly four decades, with the two meeting in their childhood and going on to land huge roles on Titanic and Spider-Man, respectively

They’ve kept their bromance tight, from starring in The Great Gatsby together and heading to events with LeBron James, to partying and hanging out with models like Neelam Gill and Rose Bertram

Not every friendship in Hollywood was built to last, but Leonardo DiCaprio and Tobey Maguire have held on firmly to their tight “bromance” since they were kids.

Tobey Maguire as Nick Carraway and Leonardo DiCaprio as Jay Gatsby in The Great Gatsby. Photo: Warner Bros. Pictures

Joining other tight male celebrity friends like Matt Damon and Ben Affleck, these former child actors have proved that fame and fortune don’t come in the way of a real, authentic friendship – something that may be hard to come by in the notoriously cutthroat world of showbiz.

This summer, The Great Gatsby actors have been making headlines for their numerous outings. They were spotted at an event in Hotel Plaza Athénée with LeBron James. They’ve been partying on yachts in Ibiza. In fact, they even have matching necklaces with wolf symbols. Both single, according to reports, with Maguire’s divorce being finalised in 2020, it seems like they’ve been enjoying the bachelor life together.

Here’s what we know about the strong bromance between these two household names.

How did Leonardo DiCaprio and Tobey Maguire meet?

Tobey Maguire and Leonardo DiCaprio in their youth. Photo: @badpostleonardo/Twitter

According to People, the pair first met in the 1980s while they were auditioning for the same roles. “I literally jumped out of the car,” DiCaprio told Esquire 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.”

An immediate friendship

Tobey Maguire and Leonardo DiCaprio have been buddies for decades. Photo: @cigarettes/Instagram

It wasn’t just acting that the kids had in common. According to Distractify, Maguire and DiCaprio share a much deeper connection, especially when it comes to family. Both raised by single mothers, these actors have opened up in interviews about how they overcame their childhood struggles.