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- The Spider-Man: No Way Home actor celebrated his birthday at a pool party on Sunday alongside celebrity friends like Leonardo DiCaprio and Kevin Connolly.
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...
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Jun 30, 2022 · The Spider-Man: No Way Home actor celebrated his birthday at a pool party on Sunday alongside celebrity friends like Leonardo DiCaprio and Kevin Connolly . In photos from the bash, a...
- The Members
- Tobey Maguire Was Leo’s Right-Hand Man
- The Unofficial Female Member
- They Were Hoodlums
- They Hounded Elizabeth Berkeley
- Leo Allegedly Propositioned A Reporter
- They Came Up Together
- Kevin Connolly Pretty Much Plays Himself on Entourage
- Harmony Korine Tried to Rob Meryl Streep
- They Loved to Brawl
Leonardo DiCaprio was the undisputed leader of the group. It simply wouldn’t have existed without him. The others basked in his glory and took advantage of the many perks that came with being a hot young movie star. The inner circle consisted of actor Tobey Maguire (freshly dusted with buzz from The Ice Storm), magician David Blaine, director Harmo...
Though David Blaine and Kevin Connolly were almost always in the mix, Leonardo DiCaprio’s first mate was Tobey Maguire. When they met as pre-teens, Leo liked the cut of Maguire’s jib so much that he tapped him for BFF status. In 2014, Leo recounted their meeting to Esquire. “I literally jumped out of the car. I was like, ‘Tobey! Tobey! Hey! Hey! An...
Though the Posse was a boy’s club, Leonardo DiCaprio recruited Sara Gilbert as the female ambassador. They met when Leo landed the prestigious role of “Darlene’s Classmate” on Roseanne. In the NY Magarticle, Sales quoted an anonymous actor, who compared Gilbert to Shirley MacLaine in the Rat Pack. She was deemed cool enough to “hang with the boys” ...
An anonymous early '90s director noted that, though Leonardo DiCaprio behaved himself when he worked in L.A., he and his pals would get up to all sorts of tomfoolery in the Big Apple. "They used to set off stink bombs at Sky Bar. But Leo's not going to act up [in LA] now. Anyone [in the movie industry] could be sitting at the next table. No one in ...
The lads were accustomed to getting what they wanted, and didn’t take rejection well. When Showgirls'Elizabeth Berkeley declined to join Leonardo DiCaprio and Jay R. Ferguson for dinner, they reportedly harassed her by phone. Then they allegedly recruited L.A. publicist Karen Tenzer to “get” Berkeley by any means necessary, including repeated phone...
One remarkable aspect of the Sales piece is that she manages to paint a vivid picture of the Posse without ever interviewing Leonardo DiCaprio. Though Sales made repeated efforts to meet up with Leo, he never returned her calls. At least not officially. Sales wrote, “One night when I got home after looking for Leo, there was a message on my answeri...
Leonardo DiCaprio’s entourage would agree that he is biggest celebrity of the bunch. But they all knew Leo before he was a major movie star. The young actors frequently ran into each other at auditions, where they were competing for the same roles. Sales quotes an actor friend of theirs in NY Mag, “They were always betting on who would blow up firs...
The hit HBO show Entourageis based on Mark Wahlberg’s real-life group of friends. Kevin Connolly’s character, Eric “E” Murphy is a composite of Marky Mark’s longtime assistant and his manager. Wahlberg knew that Connolly would be perfect for E, because they met on the set of 1995’s The Basketball Diaries. Connolly wasn’t in the movie. He was there ...
Harmony Korine mined his own troubled life for his 1995 screenplay Kids. But becoming a successful filmmaker wasn’t enough to break him of old habits. In 1998, Korine was scheduled for his fourth appearance on The Late Show. but he never made it to air. David Letterman declared that Korine was henceforth banned from the show but declined further co...
Violence seemed to follow the Posse everywhere they went. Of course, there’s the Elizabeth Berkeley incident incited by Leonardo DiCaprio and Jay R. Ferguson. But paparazzo John Barrett told Sales that Leo’s unofficial bodyguards were also keen to protect their boy from anyone they thought was infringing on his carefree lifestyle. “’They were rushi...
Jun 29, 2022 · Tobey Maguire channeled his youthful side to celebrate his birthday this year, throwing a classic pool party with A-list pals like Leonardo DiCaprio and Kevin Connelly.
- Caitlyn Becker
- 1 min
May 16, 2023 · Maguire, Haas, and Suplee were seated by Connolly's side in a 2015 Instagram photo of a Pussy Posse reunion, while a man whose face appeared to be DiCaprio had his face covered by a gold star. Leonardo DiCaprio and his group of less famous friends besieged the streets of New York City in 1998.
May 29, 2020 · One of the longest-lasting Hollywood friendships is between none other than The Great Gatsby co-stars Leonardo DiCaprio and Tobey Maguire. But how did they meet? And are Leo and Tobey still friends today?
May 9, 2022 · But beneath their hard-partying ways is a friendship between DiCaprio and Maguire that's lasted for decades. The two first met – quite literally – on the street of all places, when DiCaprio recognized Maguire from the window of his mom's car.
