Leonardo DiCaprio’s friendship with Tobey Maguire has seemingly been his longest relationship to date.

The buds met as child actors in the ’80s while they were auditioning for the same roles. DiCaprio revealed he was determined to make Maguire his friend when he saw him on the street as DiCaprio and his mom drove by.

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“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.

Maguire and Dicaprio’s connection blossomed as they bonded over shared experiences in the industry. Decades later, the twosome remain close friends who’ve both starred in movies together and taken vacations together.

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

Leonardo DiCaprio and Tobey Maguire s Epic Bromance Over the Years Costars Yacht Buddies and More 337

1992
Years after meeting in Los Angeles, Maguire and Dicaprio worked together for the first time on the film This Boy’s Life. Both actors auditioned for the lead role, but DiCaprio ultimately scored the part and Maguire took a small role in the flick.

Leonardo DiCaprio and Tobey Maguire s Epic Bromance Over the Years Costars Yacht Buddies and More 338

2009
The duo were all smiles as they attended a Lakers Game at the Staples Center.

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2011
Nearly a decade after their first film role together, DiCaprio and Maguire reunited for the film adaptation of The Great Gatsby, in which they played protagonists Jay Gatsby and Nick Carraway, respectively. The pair seemingly shared plenty of laughs while 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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