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Lawsuits, lap dogs, and lady-killing: whatever happened to Leonardo DiCaprio's 'Pussy Posse'? 

The Wolf Pack: David Blaine, Leonardo DiCaprio and Lukas Haas in 1995
The Wolf Pack: David Blaine, Leonardo DiCaprio and Lukas Haas in 1995 Credit: getty

In 1998, New York City’s streets were under siege from the most famous movie star in the world and his collection of less-handsome and less-famous friends. They didn’t call themselves the "Pussy Posse", or so they have insisted, but it was a name that came to define their exploits.

Their leader, a tousle-haired 23-year-old by the name of Leonardo DiCaprio, was fresh from Titanic, a regular at hotspots like Spy and the Bubble Lounge, and obsessed over by legions of screaming women. Models were permanently attached to his arm, and his goals involved working with cinema’s greatest auteurs and bedding as many beautiful women as possible.

Swap out some ages and the names of nightclubs, and the image of DiCaprio '98 isn’t much different from the DiCaprio of today. Save for a bit of a belly, the Oscar-winning star of Once Upon a Time in Hollywood has more or less remained consistent in the years since – his latest girlfriend, the actress Camila Morrone, was just five months old when Titanic was released, bringing to mind the old adage, a spin on a classic line from Richard Linklater’s Dazed and Confused, that while DiCaprio might age, his squeezes stay the same.

But those that once surrounded him have more or less scattered. These men have historically included bonafide “names” like Tobey Maguire, along with eternal supporting-actors like Lukas Haas, Ethan Suplee and Kevin Connolly, vaguely recognisable actors like Jay R Ferguson, and starrier non-actors like filmmaker Harmony Korine and magician David Blaine.

There was the occasional woman, too, notably actress Sara Gilbert or the musician Jenny Lewis. Most, like DiCaprio, were former child actors, regulars on the same audition circuit whose individual fortunes had balanced out in the early 1990s, before DiCaprio outpaced them all with almost staggering ease.

Leonardo DiCaprio and David Blaine in 1997 Credit: Ron Galella

Since 1998, the Pussy Posse - as they'll forever be known - have dwindled, individually settled down, been divorced or disinvited from the group chat. Their legend, however, remains intact – forever embodying vaguely grotesque Hollywood party boys whose embarrassing sleaziness is only concealed by a sheen of movie-star respectability.

Back then, there were two DiCaprios at work. There was the DiCaprio of the Seventeen Magazine covers and The Man in the Iron Mask; a teen-dream pin-up known to be thoughtful and serious, with a personal life largely ambiguous outside of a fierce devotion to his mother Irmelin. Then there was another side, one that was more covert if very public if you moved in the right circles: a world of supermodels and bed-hopping and drunken street brawls outside of New York nightclubs.

The latter didn’t truly go public until Nancy Jo Sales’s “Leo, Prince of the City”, an infamous bit of reportage published in the summer of 1998 by New York Magazine, which would rapidly become the “Frank Sinatra Has a Cold” of the Nineties. With neither DiCaprio nor his friends willing to speak on the record, Sales instead followed the Posse across the city’s club circuit, interviewing security guards, publicists, paparazzi photographers and women who had stumbled into their crosshairs. The results remain iconic, if entirely unpleasant.

Nancy Jo Sales's 1998 New York magazine cover story on Leonardo DiCaprio and his cohorts

The image Sales creates is of a sleazy man-child awash in sex, power and money, whose entourage of arrogant, frat-boy party pals both enabled and exploited his worst instincts. Now actors comfortably ensconced under DiCaprio’s shadow, their respective fames had firmly stalled. “Some of them have completely lost their careers,” an unnamed actor tells Sales. “All they do now is hang out with Leo. If Leo wants to go to Paris, it’s let’s go to Paris. Las Vegas? No problem… The people closest to him have Leomania worse than anyone.”

The story is full of priceless anecdotes. DiCaprio doesn’t carry his own money, it claims, leaving his friends to foot the bill wherever they go. There was an incident in which they were seen throwing grapes at paparazzi, another in which they were seen throwing trash down onto the speeding cars below the Brooklyn Promenade, before being driven away by DiCaprio’s personal driver.

In the story’s worst aside, the Showgirls actress Elizabeth Berkley is described as having been pressured into attending a VIP after-party at the behest of DiCaprio and Ferguson, but only if she leaves her long-time boyfriend at home. Berkley declines the invitation, but is then repeatedly called by Ferguson and a publicist.

“She said, ‘Your presence is requested here’,” Berkley recalled to Sales. “Her tone was very impatient. And I said, ‘What, are you trying to deliver me to these guys, Karen?’” Later, Berkley’s boyfriend confronts the posse at dinner, but it then descends into a street brawl outside of the restaurant, leading to Berkley’s boyfriend being assaulted by an unknown man.

Q-Tip, Harmony Korine, Leonardo Dicaprio and Michael Rappaport in New York, 1998 Credit: redferns

In 2000, DiCaprio denied to Rolling Stone that he was involved in the assault on Berkley’s boyfriend, and similarly denied that he was, at any point, an out-of-control party animal. “Truly 90 per cent of what was written about me was fabricated,” he said. “The core might come from somewhat real events, but it’s turned into something completely different. I don’t want to get into specifics, because it’s just a waste of time, but I will comment on one. I don’t know where it was coined, but they started calling me and my friends the Pussy Posse, and I think it’s the most degrading thing toward women I’ve ever heard in my life. I’ve never used that term in my entire life.”

That the tabloids, and even New York Magazine, had concocted such an elaborate ruse about DiCaprio’s personal life wasn’t too tricky to believe. Unfounded rumours that DiCaprio was gay, part of a new-age pyramid-scheme or a tragic River Phoenix-in-waiting were part and parcel of his fame towards the end of the Nineties. But something that only enhanced the speculation was a movie DiCaprio tried everything in his power to bury.

The character DiCaprio plays in Don’s Plum, a starry sort-of student film about rich and unpleasant 20-somethings in Los Angeles, isn’t far off from the DiCaprio painted by Sales. Shot over the course of one night in 1995, Don’s Plum revolves around a group of friends who gather at the diner of the title to swear at each other, talk about their sex lives and call each other “bro”.

Improvised by its cast on set, the film stars DiCaprio along with Pussy Posse luminaries Maguire, Connolly, Suplee and forgotten hanger-on Scott Bloom. Intended to be an ensemble film, with Jenny Lewis, Heather McComb and Meadow Sisto the token women of the group, everyone instead orbits around DiCaprio’s character, hanging on his every word.

“There was a hierarchy in Hollywood at that time. And Leo stood right at the top of it,” writer and producer Dale Wheatley told Vanity Fair in 2016. “Everybody else fell into place, scrambling for second and third place. People vied for that position. And Tobey very blatantly talked about—not just taking that position—but becoming number one.”

Leonardo Dicaprio and Jay Ferguson in the Bahamas, 1998 Credit: hulton

Watched today, there is no question as to why DiCaprio wanted no one to see Don’s Plum. An ugly, disquieting watch, it is Clerks by way of American Psycho, with DiCaprio playing a slovenly, abusive and arrogant creep with a penchant for scattalogical humour who is consistently vile towards women.

Introduced with his hands down his pants and explaining his eagerness to “find some chicks tonight,” he hits rock bottom soon after. Sat at a diner table, he erupts in laughter when a large black woman walks past. “Send her back to sea, bro, that chick is fat,” he remarks. “She was like a f------ tank walking by, bro.”

When a newcomer to the group, played by Buffy the Vampire Slayer’s Amber Benson, condemns DiCaprio’s character for his treatment of women, he threatens her. “How about I take my shoe and shove it in your mouth, how about that? You f------ paranoid freak.” Seconds later, he calls her a “f------ piece of shit hippie c---” before threatening to “f------ throw a bottle at your face, you f------ whore”. Benson’s character is told off by DiCaprio’s friends, and encouraged to leave the diner. She smashes the windows of DiCaprio’s car outside, but is otherwise never seen again.

Through the rest of the film, DiCaprio’s character boasts of his sexual prowess, recalling a time he used a vegetable to satisfy his girlfriend, and asking dim questions like, “Do girls masturbate at all?” He makes incest jokes and continues to threaten women, before confessing later that he’s only the way he is because his father killed himself.

According to Don’s Plum lore, DiCaprio verbally agreed to star in the film, shot his scenes in a single night and was then shocked to discover Wheatley and director RD Robb were attempting to sell the film to studios. Offers to buy the film were reportedly withdrawn soon after, with DiCaprio and Maguire both insisting that they believed they were shooting a short film as a favour to a friend, and not an actual feature. Producer David Stutman then sued the pair, claiming that they had “carried out a fraudulent and coercive campaign to prevent release of the film.” 

Stutman’s lawsuit also alleged that “Maguire and his manager had determined that, in the film, Maguire did not come off as strong a ‘leading man’ as DiCaprio and that some of the improvisational comments Maguire had made during the film revealed personal experiences or tendencies that would undermine the public image he and his manager were trying to project”.

Testifying against the Don’s Plum crew, DiCaprio suggested that his resistance to the film’s release came from feeling betrayed by former friends. “Number one, first and foremost, the agreement had always been that this was a short film,” he said. “I never had any intention of doing a feature film. Whatsoever. When I do a feature film, I have lots of rehearsal. I have script meetings. It takes weeks and weeks and weeks. And I shoot for months and months, up to six months, up to seven months at a time. I would never go in for one night and improvise with my friends and make a feature film. There’s no way I would ever do that.”

“Why did I care?” he continued. “These guys were my friends. And how could they try and change what our word was by editing a feature film? It was a shock to me.”

In 1999, Wheatley and Robb were encouraged to settle with Maguire and DiCaprio, having lost most of their money due to legal fees, and been ostracised from Hollywood as a result of the scandal. In accordance with the settlement, Don’s Plum has never been released in the US or Canada, while Wheatley’s attempts to publish the film for free online in 2016 were quashed by lawyers for the actors. It is currently streaming on YouTube, but could be taken down any day now.

But while DiCaprio and Maguire were vaguely victorious in their war against Don’s Plum, it also appeared to dim the Pussy Posse’s ubiquity, or at least encouraged them to stay indoors more. Since the days of Don’s Plum and “Leo, Prince of the City”, Maguire became Spider-Man and got married, Connolly was cast as the second-string hanger-on to a movie star on the long-running bromantic comedy series Entourage, and Suplee and Ferguson became TV regulars, the former best known for My Name Is Earl and the latter Mad Men, where he played Elisabeth Moss’s office mate and eventual love interest Stan Rizzo.

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Fight night with the boys in Vegas... BIG night!!!!

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Bloom vanished, Korine got married and makes trash epics like Spring Breakers and The Beach Bum. Haas is a jobbing actor, appearing in last year’s Widows and alongside DiCaprio in films like Inception and The Revenant. Blaine is currently under investigation by the New York police department over allegations of sexual assault (he has denied all allegations). Wheatley, meanwhile, is clearly still furious with DiCaprio and desperate to #FreeDonsPlum.

As for DiCaprio, he has by all accounts calmed down since his Pussy Posse heyday, the actor more likely to be found reclining on private yachts with women barely in their 20s rather than getting sloshed at nightclubs with women barely in their 20s. And there’s been hints in recent years that he may be embarrassed by being publicly associated with his old pals. When Connolly posted an image of a Pussy Posse reunion to his Instagram in 2015, with Maguire, Haas and Suplee sat by his side, a man believed to be DiCaprio had his face concealed under a gold star.

It hasn’t stopped the group from occasionally resurfacing since, however. When DiCaprio finally won his Oscar in 2016, he immediately hooked up with Haas and Maguire and brought them to the Vanity Fair Oscar Party, where the trio shared the same vape (aww) and were overheard chanting “Wolf Pack!” and “howling like wolves all night,” a source told the New York Daily News.

DiCaprio, once again, was the star of the night – his friends forever in his orbit.