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  2. Aug 21, 2019 · 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...

    • Kylie Hemmert
  3. May 9, 2022 · Before there was "Entourage" on HBO, there was the real-life "P***y Posse," led by a young Leonardo DiCaprio and comprised of his closest friends, like Lukas Haas, Kevin Connolly, Harmony Korine, Ethan Suplee, David Blaine, and of course, his BFF, actor Tobey Maguire.

    • Lana Schwartz
  4. Apr 13, 2020 · Maguire ended up getting a supporting role as one of DiCaprio's friends, just as the pairs real life friendship was growing. After This Boy's Life, DiCaprio was cast in What's Eating Gilbert Grape, alongside Johnny Depp, and DiCaprio's fame skyrocketed just at the age of 19.

    • Contributor
  5. Aug 25, 2023 · 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.

    • Faye Bradley
  6. May 29, 2020 · So, yes Leo and Tobey are still friends in 2020. We don’t hear much from Tobey nowadays, though he recently lent his voice as the narrator of the animated film The Boss Baby (2017). As for Leo, the Oscar winner has a few upcoming projects, including a role as Theodore Roosevelt in Roosevelt .

  7. Jan 22, 2022 · It’s not the most auspicious of starts, but actors DiCaprio and Maguire have been friends for a very long time. The pair worked together on This Boy’s Life, a second time for the indie flick Don`’s Plum and were reunited for a big-screen adaptation of The Great Gatsby.

  8. Apr 30, 2017 · Leonardo DiCaprio and Tobey Maguire shared the big screen as pals Jay Gatsby and Nick Carraway in 2013's The Great Gatsby, but their real-life relationship started long ago. Leo and Tobey...