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  1. According to Complex, DiCaprio's infamous group began with Leonardo DiCaprio, Tobey Maguire, Kevin Connolly, and Lukas Haas. They were known to chase girls, set off stink bombs at Sky...

  2. May 9, 2022 · While it might seem like Leonardo DiCaprio and Tobey Maguire should have been competitors – as they were auditioning for the same roles – the two have been supportive of each other throughout the years, with Maguire hoping to take more of a Tom Hanks route and DiCaprio envisioning himself as the next Jack Nicholson (via Rare).

    • Lana Schwartz
  3. Aug 12, 2024 · Tobey Maguire and Leonardo DiCaprio were among the bunch of actors who got their breakthrough in the 90s with many acclaimed performances. DiCaprio starred in some of his most seminal work in the decade with films like What’s Eating Gilbert Grape, This Boy’s Life, and Romeo + Juliet.

  4. Oct 19, 2024 · Leonardo DiCaprio and Tobey Maguire deliberately tried to ban their own film, the indie '90s feature Don's Plum, for a variety of reasons.

    • Witney Seibold
  5. Feb 7, 2022 · Tobey Maguire and Leonardo DiCaprio have been close friends for decades. Here's a list of every movie the two talented actors have done together over the years.

  6. Oct 14, 2022 · It’s well-documented that Tobey Maguire and Leonardo DiCaprio are good pals. For a time, the duo were part of an illicit partying collective, the poorly named ‘Pussy Posse’, which also featured the likes of Lukas Haas, Kevin Connolly, Harmony Korine, Ethan Suplee and David Blaine.

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  8. Jan 22, 2022 · “A little competition rose up between them,” an anonymous actor told Nancy Jo Sales. “They were always betting on who would blow up first.” DiCaprio and Maguire could occasionally be spotted at Victoria’s Secret events in New York City, or on impromptu visits to American playground, Las Vegas.