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The Wolf of Hollywood: Inside the sex, parties and lawsuits of Leonardo DiCaprio’s rogue boy gang ‘Pussy Posse’

Leonardo DiCaprio and his group of less famous friends besieged the streets of New York City in 1998
UPDATED MAY 16, 2023
Pussy Posse members- (L-R) Lukas Haas, Leonardo DiCaprio, Kevin Connolly, and Tobey Maguire (Dimitrios Kambouris, Vivien Killilea/Getty Images)
Pussy Posse members- (L-R) Lukas Haas, Leonardo DiCaprio, Kevin Connolly, and Tobey Maguire (Dimitrios Kambouris, Vivien Killilea/Getty Images)

NEW YORK CITY, NEW YORK: Leonardo DiCaprio is free to pursue his interests, especially after he received an Oscar. The man has always followed his heart, long before being recognized with acting's highest prize. The megayacht owner and environmentalist often attend Lakers games when he's not dining at Carbone with a model under the age of 25. And when he's not at a Lakers game, he's out having fun with Tobey Maguire and Kevin Connolly from Pussy Posse.

One might remember the term Leo and his gang of womanizing friends got themselves in the 1990s - Pussy Posse. But it became apparent following the 2016 Oscars that the group had drastically changed that name since then. Partygoers informed that "they (apparently) called themselves The Wolf Pack," The New York Daily News reports.

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What was The Pussy Posse?

For 'Pussy Posse' to be properly appreciated, we must return to a pre-recession, prelapsarian New York City where Leo and his friends visited clubs with names after random creatures and deadly acts. We are referring to Nancy Jo Sales' renowned 1998 New York profile of a young man, "Leo, Prince of the City," and his devoted brothers, The Daily Beast reports.

Before 'Entourage,' there was Pussy Posse, a patchwork of young actors and former child stars that included Tobey Maguire, Lukas Haas, Harmony Korine, Jay Ferguson, David Blaine, Josh Miller, Kevin Connolly, Ethan Suplee, Justin Herwick, Scott Bloom, and occasionally Sara Gilbert.

Leonardo DiCaprio (R) and Tobey Maguire (L) attend the Los Angeles Lakers vs Utah game at Staples Center on April 27, 2009 in Los Angeles, California.
Leonardo DiCaprio (R) and Tobey Maguire (L) attend the Los Angeles Lakers vs Utah game at Staples Center on April 27, 2009, in Los Angeles, California (Noel Vasquez/Getty Images)

Actors Leonardo DiCaprio and Lukas Haas pose with director Kevin Connolly at the premiere of
Leonardo DiCaprio and Lukas Haas pose with director Kevin Connolly at the premiere of 'Gardener Of Eden' at the 2007 Tribeca Film Festival on April 26, 2007, in New York City (Bryan Bedder/Getty Images)

Connolly told The Daily Beast of the New York magazine article, "I have read it, The truth of the matter is [Sales] coined that phrase, and it stuck. Hand on the Bible as we sit here, never did myself or any of our friends refer to ourselves as ‘The Pussy Posse.’ She wrote it in an article, and it stuck." Connolly further added, "There was this idea that we were rolling around referring to ourselves as that, and that’s just not true. It would be absolutely ridiculous. But she said it, and it stuck. We were young and if we did say that in passing it would be something we’d have to live with, but we never said that. But it was a good time."

Leonardo DiCaprio (R) and Kevin Connolly (L) attend the Los Angeles Lakers vs Utah Jazz game at Staples Center on April 21, 2009 in Los Angeles, California.
Leonardo DiCaprio (R) and Kevin Connolly (L) attend the Los Angeles Lakers vs Utah Jazz game at Staples Center on April 21, 2009 in Los Angeles, California (Noel Vasquez/Getty Images)

The Pussy Posse, an LA native, invaded NYC like an army while carrying the "no homo" flag. Sales claimed that Leo's pals yearned to be around him constantly. They went to work with him, served as his "unofficial" bodyguards, and also handled the actor's money. The Pussy Posse soon gained a reputation for treating women with more disdain than a black teen at a Trump rally.

How did Leonardo DiCaprio's 'Pussy Posse' fare?

When not serving as modified man does, The Pussy Posse dropped stink bombs at Sky Bar, broke into Victoria's Secret parties without permission, made last-minute visits to Vegas, and wandered neighborhood bars and nightclubs. The fresh-faced aficionados of the Meatpacking District could be seen tossing rubbish from the Brooklyn Promenade into the street below or tossing grapes at paparazzi from above at the Mercer Hotel.

Sales came across a few instances of open misogyny along with the usual complaints of lecherous actions, player mentalities, and an absolute incapacity to tip strippers. The 'Showgirls' actress Elizabeth Berkley made the terrible error of entering the VIP area during the premiere of 'The Man in the Iron Mask,' which led to one of the most bizarre occurrences. She had no idea that she was going into the wolf's den.

After spotting Berkley among the crowd, the Pussy Posse sent LA publicist Karen Tenser to go get her. "Jay Ferguson and Leo are going crazy for you, and they want you to come to Elaine’s after this," she declared. Berkley, who at the time was seeing actor Roger Wilson, kindly declined. Tenser and Ferguson, allegedly, called Berkley often to invite her out to dinner and other activities. Wilson chose to intervene after the harassment became out of control.

Actress Elizabeth Berkley introduces the Cinespia Screening of
Elizabeth Berkley introduces the Cinespia Screening of 'Showgirls' at the Hollywood Forever Cemetery on June 27, 2015, in Hollywood, California (Michael Buckner/Getty Images)

The Prince of the City

Leo DiCaprio, the leader of Pussy Posse, was a 23-year-old with tousled hair who had just finished filming 'Titanic.' He frequented hotspots like Spy and the Bubble Lounge and was wooed over by throngs of shouting women. His objectives included collaborating with the best auteurs in cinema and dating as many attractive ladies as he could while models were ever-present around his arm, as per The Telegraph.

The portrayal of Leonardo DiCaprio in 1998 wouldn't have changed much if you changed a few details, like the names of the clubs. The Oscar-winning star of 'The Revenant' has largely remained the same over the years. His most recent girlfriend, actress Camila Morrone, was only five months old when 'Titanic' was released, which makes the old saying that while DiCaprio may get older, "his squeezes stay the same."

Actor Leonardo DiCaprio and his girlfriend, model/actress, Camila Morrone watch the Men's Singles final match between Daniil Medvedev of Russia and Novak Djokovic of Serbia on Day Fourteen of the 2021 US Open at the USTA Billie Jean King National Tennis Center on September 12, 2021 in the Flushing neighborhood of the Queens borough of New York City.
Leonardo DiCaprio and his girlfriend Camila Morrone watch the Men's Singles final match on September 12, 2021, in the Flushing neighborhood of the Queens borough of New York City (Sarah Stier/Getty Images)

The portrayal of DiCaprio by Sales is very accurate for the part he portrays in 'Don's Plum,' a star-studded student movie about wealthy and unhappy 20-somethings in Los Angeles. The movie, which was improvised on-site by its actors, features DiCaprio as well as notable Pussy Posse members Maguire, Connolly, Suplee, and overlooked hanger-on Scott Bloom.

Where are the 'Pussy Posse' members today?

Since 1998, the Pussy Posse—as they'll always be called—have diminished, each settled down, gotten married, or been kicked out of the group chat. They continue to be associated with vaguely hideous Hollywood party boys whose humiliating sleaziness is only covered up by a veneer of respectability befitting a movie star, yet their legacy endures.

The actor is more likely to be found lounging on private boats with ladies in their 20s than getting wasted in nightclubs with women in their 20s. As for DiCaprio, he has reportedly cooled down since his Pussy Posse heyday. Additionally, there have been suggestions in recent years that he could feel ashamed to be seen with his old friends in public. 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.



 

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