Leonardo DiCaprio and Tobey Maguire’s Epic Bromance Over the Years

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

Leonardo DiCaprio’s friendship with Tobey Maguire has endured as his longest-standing relationship to this day. The two first crossed paths as young actors in the 1980s, frequently auditioning for the same roles. DiCaprio fondly recounted the moment he spotted Maguire on the street while driving with his mother, leaping out of the car with excitement to greet him. In a 2014 interview with Esquire, DiCaprio shared, “I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah—I know you. You’re … that guy.’ But I simply made him my friend. When I want someone to be my friend, I just make them my friend.”

Over the years, Maguire and DiCaprio’s bond has deepened as they shared their experiences and journeys in the entertainment industry. Their connection has remained steadfast, with both of them starring in movies together and even embarking on vacations as close companions.

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


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.


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


After almost ten years since their initial collaboration, DiCaprio and Maguire serendipitously reunited for the cinematic adaptation of “The Great Gatsby.” In the film, DiCaprio portrayed the enigmatic Jay Gatsby, while Maguire took on the role of the observant Nick Carraway. The set was filled with an air of camaraderie as the duo appeared to share numerous lighthearted moments and laughter during the production of the movie.


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

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