Not every friendship in Hollywood was built to last, but Leonardo DiCaprio and Tobey Maguire have held on firmly to their tight “bromance” since they were kids
Inside the legendary friendship between Leonardo DiCaprio and Tobey Maguire, from their childhood in Hollywood to their costarring roles in The Great Gatsby, to their yacht parties with models Neelam Gill and Rose Bertram
While not every Hollywood connection is meant to stay, Leonardo DiCaprio and Tobey Maguire have clung to their close “bromance” since their early childhood.
These former child actors, who have teamed up with other close male celebrity pals like Matt Damon and Ben Affleck, have demonstrated that success and wealth do not preclude genuine friendships, which may be difficult to find in the infamously competitive entertainment industry.
Actors from The Great Gatsby have been in the news this summer for their many appearances. They were seen with LeBron James at a Hotel Plaza Athénée function. They have been having parties in Ibiza on yachts. They even have matching necklaces with emblems of wolves, in fact. Both reportedly single, it appears that they have been enjoying their single status together. Maguire’s divorce was finalized in 2020.
What is known regarding the close kinship between these two well-known names is as follows.
How did Leonardo DiCaprio and Tobey Maguire meet?
People claims that the two met during their auditions for the same jobs in the 1980s. 2014 saw DiCaprio say, “I literally jumped out of the car,” to Esquire. “I thought, ‘Tobey! Tobey!'” Hi there! Hello there! He responded, “Oh, yeah, I know you.” You’re that guy. But now I’m friends with him. I simply add people as friends when I want them to be mine.
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An immediate friendship
The children shared more than just their acting skills. Distractify claims that there is a deeper bond between Maguire and DiCaprio, particularly in terms of family. These actresses, who were both raised by single mothers, have talked candidly about how they overcome adversity in their early lives in interviews.
Maguire said to People in 2007 that he had “difficult, emotional, and scary times as a kid” as a result of his parents divorcing when he was three years old and him being raised by other family members. According to DiCaprio’s interview with CBS Sunday Morning, he was robbed when he was approximately five years old. His parents divorced when he was a baby, and he grew up in a “hardcore neighborhood.”
According to rumors, DiCaprio and Maguire were members of the ill-famous “P*ssy Posse,” a group of brothers, in the 1990s. According to The Daily Beast, the group also allegedly includes Lukas Haas, Harmony Korine, David Blaine, Jay Ferguson, Josh Miller, Ethan Suplee, Kevin Connolly, Scott Bloom, Justin Herwick, and occasionally Sara Gilbert. They were renowned for controlling the nightlife scene in New York.
Although it’s unclear if this pack ever existed or what kinds of mischievous activities they engaged in, Ranker reports that it has since been dubbed the “Wolf Pack.”
Starring in films together
Either way, the boys have come a long way since the 90s, and have grown up to enjoy fame and success with a more low-key approach.
They’ve also starred in a string of films together, including Don’s Plum (2001), This Boy’s Life (1993) and The Great Gatsby (2013).
DiCaprio’s bond with Maguire’s kids
Maguire and his ex-wife Jennifer Meyer have two teenage children together, Ruby and Otis. Despite not having children of his own, DiCaprio seems to be a natural with his closest friend’s kids, according to Popsugar. According to the same source, the Titanic actor would like spending time with his family at beachside restaurants and brunches and would be a “great dad.”
Furthermore, according to The Things, Maguire appointed DiCaprio Ruby’s godfather in 2006.
Partying, yachts and hanging out with models
Now, nearly four decades later, these long-time pals, both single, are enjoying the high life together – and that includes plenty of five-star holidays, yachts, hang-outs with models and A-list parties.
They took a vacation together to St. Tropez last year. They’ve been out to far more parties this year, including a night at Paris’ Hôtel Costes, boat rides around the French Riviera with Indian-British model Neelam Gill and Dutch model Imaan Hammam, and strolls through New York City with Ukrainian model and activist Alina Baikova. They were sighted in August with Belgian model Rose Bertram at an after-party in Paris. They later traveled to Spain for another boat trip with Arabella Chi, the star of Love Island.