The Unbreakable Bond: Inside Leonardo DiCaprio and Tobey Maguire's Timeless Bromance

Leonardo DiCaprio and Tobey Maguire have maintained a strong friendship, which appears to be his longest-lasting relationship so far.

Meeting as child actors in the 1980s while both auditioning for the same roles, DiCaprio was instantly captivated by Maguire when he spotted him on the street while driving with his mother.

DiCaprio recounted the incident to Esquire in 2014, revealing his animated reaction upon spotting Maguire. "I literally jumped out of the car," he exclaimed. "I was like, 'Tobey! Tobey! Hey! Hey!' And he was like, 'Oh, yeah — I know you. You're ... that guy.' However, I effortlessly forged a friendship with him. When I desire someone to be my companion, I simply make them my companion."

Maguire and DiCaprio's bond flourished as they discovered commonalities within the industry. Over the course of several decades, they have maintained a strong friendship, frequently starring in films together and embarking on joint vacations.

Keep scrolling to see Dicaprio and Maguire’s bromance over the years:

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Leonardo DiCaprio and Tobey Maguire’s Epic Bromance Over the Years: Costars, Yacht Buddies and More

Leonardo DiCaprio and Tobey Maguire have been friends for what appears to be the longest period in DiCaprio's dating history. They first crossed paths as young actors in the 1980s while both were auditioning for various roles. DiCaprio shared his determination to establish a friendship with Maguire after spotting him on the street while driving with his mother.

DiCaprio exclaimed to Esquire in 2014, "I leaped out of the car with excitement! I called out to Tobey multiple times, desperately trying to get his attention. He recognized me but only as 'that guy.' Nonetheless, I managed to turn him into my friend, as that's how I approach forming friendships."

As they forged a connection based on their mutual experiences in the industry, Maguire and DiCaprio's relationship flourished. Over the course of decades, the duo has not only acted alongside each other in films but has also enjoyed vacations together, maintaining their close bond.

Keep scrolling to see Dicaprio and Maguire’s bromance over the years:

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1992

Years later, after their initial encounter in Los Angeles, Maguire and DiCaprio collaborated for the very first time on the movie This Boy's Life. Both actors participated in auditions for the leading role, however, DiCaprio ultimately landed the part while Maguire settled for a minor role in the film.

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2009

The duo were all smiles as they attended a Lakers Game at the Staples Center. 

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2011

Nearly ten years after their initial collaboration on screen, DiCaprio and Maguire teamed up once again for the cinematic interpretation of The Great Gatsby, taking on the roles of the main characters Jay Gatsby and Nick Carraway. Throughout the filming process, the duo appeared to have a delightful time together, sharing laughter and creating a joyous atmosphere on set.

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2013

Two years after filming Gatsby, Maguire and DiCaprio attended the Cannes Film Festival premiere of the film.

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2022

The pals were spotted on vacation in St. Tropez. Before heading to their yacht, DiCaprio and Maguire took a walk around the marina. 

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July 2023

Maguire and DiCaprio returned to the south of France the following year for another yachting adventure. 

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August 2023

One month after their stay in St. Tropez, the friends were spotted on a boat in Ibiza, Spain.