Tobey Maguire, Leonardo DiCaprio: Besties Since The ’80s


Tobey Maguire and Leonardo DiCaprio are best friends whose relationship spans longer than 30 years. The Spider-Man star and the Titanic heartthrob have partied together and bonded over their challenging upbringings and high-flying careers in the entertainment industry. Both of them understand the myriad perks and pressures that characterize celebrities’ lives.

Even after so much time as friends, they love hanging out together. Most recently, People reported that the pair celebrated Maguire’s 47th birthday together at a laid-back pool party. Here’s a comprehensive look at the dynamic duo’s long-spanning friendship as well as their support for each other over the years.

Maguire And DiCaprio Met As Aspiring Child Actors

In 2014, Esquire shared the story of how the lifelong friends met, and it sounds like an encounter scripted for a movie. When DiCaprio was around 12 years old, his mother was driving him around Los Angeles when he spotted a boy his age on the street filming a television show. DiCaprio immediately recognized him from auditions the pair had done.

“I literally jumped out of the car,” DiCaprio recalled years later. “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.”

Maguire and DiCaprio were drawn together by their similar backgrounds and shared experiences as child actors. They knew first-hand the intense competitiveness that defines the entertainment world and the disappointment that comes from failing to land a dream role.

The boys shared dysfunctional family lives as well. DiCaprio was raised in a dangerous neighborhood after his parents’ divorce. He told CBS Sunday Morning that there was a prostitution ring nearby, drug addicts in the alleyway, and he “got sort of robbed at five years old.”

Maguire’s parents split up when he was 3, and he was passed between different family members throughout his early years. When speaking of his unsettled childhood, he sounded like he had moved on. According to People, Maguire said, “My feelings of love or security or happiness—they were all in my own hands. I had plenty of difficult, emotional, and scary times as a kid, but I don’t dwell on it.”

They Have Supported Each Other Personally And Professionally For Decades

While they’ve appeared together in This Boy’s Life (1993) and The Great Gatsby (2013), Maguire and DiCaprio never let professional ambition derail their relationship—not even when they have gone after the same roles. For example, Maguire was edged out by DiCaprio for a prominent part in the short-lived TV series Parenthood (1990). Hard feelings weren’t in the equation for them after DiCaprio got the meatier part and Maguire was left with a minor one.

The explanation is simple. “Leo and I have a lot of trust and respect for each other,” Maguire told People in 2013, when director Baz Luhrmann’s film adaptation of The Great Gatsby was about to be released. Both of them had roles in the blockbuster: DiCaprio as titular tycoon Jay Gatsby, and Maguire as his friend, Nick Carraway.

“We can joke with each other about competition, said Maguire, “but are supportive. I have a whole bunch of friends like that.”

(L-R):Tobey Maguire, Baz Luhrmann, Carey Mulligan, and Leonardo DiCaprio posing at Cannes film festival
(L-R) Tobey Maguire, Baz Luhrmann, Carey Mulligan, and Leonardo DiCaprio pose to promote “The Great Gatsby.” (VALERY HACHE/AFP via Getty Images)

DiCaprio has also stepped up for Maguire at times. An independent film made on a shoestring budget, Don’s Plum (2001), featured a bunch of actors talking off the cuff and gabbing candidly about various topics including extremely intimate matters. Both DiCaprio and Maguire appeared in the film, but Maguire began to worry that his role could put a big dent in his clean-cut image.

According to New York magazine, Maguire thought the earthy “improvisational comments” he made on camera might come back to haunt him.

DiCaprio apparently agreed with Maguire. The Guardian reported that the pair was “involved in legal action against the [film’s] makers,” which eventually led to a settlement that barred the film from ever being shown or sold in the U.S. and Canada. However, it was shown at the Berlin Film Festival in 2001.

The close friends don’t only support each other professionally—their camaraderie carries into their personal lives as well. DiCaprio doesn’t have kids of his own, but he is close to Maguire’s children, Otis and Ruby. DiCaprio and Maguire also share a keen interest in basketball and enjoy playing casual games together as well as attending professional ones.

They’re Part Of The Same Hard-Partying Crowd

DiCaprio and Maguire used to hang out with “The P*ssy Posse,” a group of celebrities known for their rambunctious hijinks such as clubbing, womanizing, and heavy drinking. They sometimes got into fights and played pranks, which sometimes got out of hand.

New York magazine reported that the pair flung grapes at paparazzi at the Mercer Hotel and used stink bombs at Sky Bar. DiCaprio was even seen with a black eye which he got from “horsing around with his friends,” said his publicist.

Leonardo DiCaprio and Tobey Maguire have a lot in common. The two A-list actors have managed to put their career rivalry aside to sustain a decades-long friendship based upon mutual respect and loyalty. They have resolutely stood beside one another in good times and tough ones. In the relentless, pressure-cooker atmosphere of Hollywood, that is quite a notable feat.





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