The truth about Leonardo DiCaprio and Tobey Maguire’s relationship

Leonardo DiCaprio kicked off his diverse career when he was a kid, first appearing in a couple of TV series and features before What’s Eating Gilbert Grape, The Basketball Diaries, Romeo + Juliet, and, of course, Titanic, catapulted him onto the A-list, making the young actor one of the biggest movie stars in the world. Since then, DiCaprio has been a household name, stacking up his cinematic roles, nominations, and awards, even finally winning his first Oscar for Best Actor in 2015’s The Revenant.

Tobey Maguire’s career began in a similar fashion, starting young in the child acting scene, though his professional life didn’t quite take off the way DiCaprio’s did after they both appeared in 1993’s This Boy’s Life when they were teenagers. Maguire, best known for playing Peter Parker in Sam Raimi’s Spider-Man trilogy that kicked off in 2002, has a handful of acclaimed movies under his belt. In 2010, Maguire earned a Golden Globe nomination as Best Actor for his performance in the drama Brothers and only did a few more projects after that before seemingly stepping away from the acting world to focus on producing. 

DiCaprio and Maguire could have easily ended up as Hollywood rivals, as they were constantly going after the same roles ever since they were kids. Instead, the two formed a quick bond nearly 30 years ago and never looked back, even during times of controversy. This is the truth about Leonardo DiCaprio and Tobey Maguire’s relationship.

The actors have been friends for over three decades, dating back to when the up-and-coming stars were not even teenagers yet. According to a profile DiCaprio did with Esquire in their May 2013 issue, the ease of the two becoming best friends had a lot to do with the fact that they had so much in common. DiCaprio and Maguire were both raised in Los Angeles by single mothers, for example, and were both navigating the LA world of child acting in a competitive Hollywood environment. 

According to Esquire, DiCaprio sought out a friendship with Maguire when the two stars were only 12 years old. The actor was apparently heading home from school when he spotted Maguire filming a TV show in Los Angeles, recognizing the other boy from auditions for other projects. DiCaprio told Esquire that he “literally jumped out of the car” after telling his mother to stop, and excitedly began yelling “Tobey! Tobey!” to grab Maguire’s attention, sparking the beginning of a real friendship. 

Maguire told Esquire that DiCaprio’s sense of purpose is what makes him successful personally and professionally, saying, “You don’t become as successful as Leo if you don’t know how to get what you want,” even friends. DiCaprio shared that when he wants someone to be his friend, “I just make them my friend,” and the rest is history.

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