According to an onlooker, reporting to the New York Daily News, Leonardo DiCaprio celebrated his long-awaited Oscar win by partying with his close friends Lukas Haas, Tobey Maguire, and Vincent Laresca. Drinks were shared, pipes were vaped, and the crew chanted, ‘Wolf Pack, Wolf Pack, Wolf Pack!’ into the warm California evening. All of this seems rather tame by modern celebrity social standards, but Leo’s infamous “Pussy Posse” remains a quiet staple of the scene. Only this week, DiCaprio and Maguire (who recently split from his wife) were spotted grabbing lunch in New York City with Orlando Bloom, signaling a new addition to the ranks, which has at previous points included Lukas Haas, David Blaine, Kevin Connolly, Harmony Korine, and the irritating little brother from Teen Witch. Together with Maguire and Bloom, still fresh from his split from Katy Perry, the paparazzi photos were subdued, casual, and oddly uncool.
The return of the Posse to our memories reminded me of the notable absence of another ensemble of celebrity friends: The Taylor Swift squad. Following a public dragging by Kim Kardashian and a cringe-worthy showmance with Tom Hiddleston, Swift has smartly kept a low profile. Her newest relationship with another British actor, Joe Alwyn, has been reported on sparingly, and thankfully lacks the twee orchestrations of the Hiddleswift Summer, wherein the most visible private beach party of all time included personalised tank-tops and Instagram ready posing with fellow loved-up couples. If Swift is hanging with her usual crew, which includes model Karlie Kloss, actresses Ruby Rose and Jaime King, and singer Lorde, then she’s locked it down.
Friendship can be a powerful thing, fostering much needed communities and a sense of solidarity during tough times. It’s also a conveniently handy public relations goldmine. Swift knew this better than most when the time came to promote her album, 1989. This was a change for her, a step into straight pop after years with a foot in the country scene. The album features some of her strongest song-writing, and works hard to be more than a series of songs about being wronged by men, as many had accused her previous output of being. It became a game for the social media era to piece together the clues in her songs and liner notes to decipher which song was about Jake Gyllenhaal or Harry Styles or any number of famous men she’s been connected to. That’s a narrative Swift exploited frequently, but there was more to gain from a sense of solidarity, so why not make it one built on the power of female friendships?
Two events signaled Swift’s weaponizing of the squad: The 1989 world tour and the music video for Bad Blood. Swift’s tour, which played to countless sell-out audiences, turned into the ultimate catwalk, where the best and brightest could be seen appreciating Swift’s companionship. Look, there’s Heidi Klum! And the US Women’s Soccer Team! It’s Mariska Hargitay and Cara Delevingne! Now it’s Uzo Aduba and Gigi Hadid! Slow down, now it’s Serena Williams and Kendall Jenner! And there’s Lena Dunham and Hailee Steinfeld! Men did occasionally appear, often to duet with her as Nick Jonas did, but the objective was one of female empowerment, however diluted it may be presented. Every night seemed to bring with it a shiny new celebrity to adore, and a fresh swath of glowing headlines for Swift. Most of the time, these celeb pals didn’t do much - they danced, they waved, they looked like competition winners on stage with their favourite singer - but that wasn’t the point. This was a pure power play by one of pop music’s most precise schemers.
That went into overdrive with the Bad Blood video. Everyone knows the song is about Katy Perry, based on the most asinine of supposed feuds between the two, and Swift wanted everyone to know she was going to win that battle. Releasing a good diss track would be too much - and Bad Blood is most certainly not a good song - but the real death blow came from the video, which featured an overlong hype campaign where posters featuring the array of guest stars were released to fan fervour before the final show was released. Select squad members appear - Steinfeld, Hadid, Delevingne, Kloss - along with older women who really should be above all this - Hargitay, Jessica Alba, and Cindy Crawford - to tell the story of sexy spies and double crossing. It’s elaborate and thin and glossy, like all the best supermodels. It’s also staggeringly inauthentic, which is a major problem for Swift’s squad. Even if some of these friendships are real, they can’t help but play out like a performance.
For DiCaprio, the posse was just as performative, but for different means. A now infamous New York magazine profile by Nancy Jo Sales established the Pussy Posse to outsiders, focusing on then 23-year-old Leo and the young actors who orbited his rising star. The familiar markers of the Leo Life where there: Stories of young models “all over him”, the flurry of celebrities eager to sit in his presence (“He’s got rock stars, Puff Daddy, Donald Trump, going over to his table to sit with him”), impromptu trips to Vegas, and the occasional prank. Like Swift, the opposite sex was not entirely excluded from the fun, as Sara Gilbert took on the Shirley MacLaine role to this Rat Pack of the boy band era.
It would be easy to call them a frat, but that wouldn’t do the dynamic justice. This was a callback to the days of Frank, Dean and Sammy with a dewy-eyed freshness, and it was clear who was King. Leo was always defined in his group as The One: The most talented, the most handsome, the one with the best roles, the one with the hottest girlfriends, the one who had a real chance of becoming one of the greats. That seemed to define the Posse, who Sales describes as being part enraptured, part envious. At one point in the profile, someone says:
“The Titanic stuff has caused this big identity crisis. Some of them have completely lost their careers. 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.” DiCaprio was heard exclaiming to his table at Tomoe on Oscar night, “Let’s rent a plane! I want to go to India!” “The people closest to him have Leomania worse than anyone”.
Both Swift and DiCaprio exude power in their assembled parties: Swift from the clout she radiates that ensures the most beautiful and inspiring young (mostly white) women surround her to appeal to her demographic; DiCaprio through the sheer charisma that keeps those closest to him returning time and time again to sample a morsel of his shine. Why make enemies when you can neutralise the threat and welcome them into your inner circle? Luka Haas, a posse member, was someone Leo beat out for roles in This Boy’s Life and What’s Eating Gilbert Grape? Lorde’s first mention of Taylor Swift in the press was a dig at her being “too flawless and unattainable”, but one big bunch of flowers sent to her by Swift to congratulate her success later and the pair became as thick as thieves. Let’s not forget the Nicki Minaj incident, a minor flurry that exposed some of Swift’s white privilege regarding the music industry, but was solved just in time for the pair to perform hand in hand at the MTV VMAs.
It’s hard to talk about either Swift or DiCaprio and their respective friends without talking about how we view male and female friendships. Men are given the benefit of easy going camaraderie, and a rather simple assumption of their aims, bound together by booze and boobs and boisterousness. They don’t get smeared as catty or bitchy or inherently untrustworthy in the way women’s friendships do. A gathering of women in common interest inspires talk of covens and insidious scheming. We’re constantly questioning the ulterior motives (which I’m perfectly aware I’m doing here too) or wondering when a man is going to inspire the break-up fights. DiCaprio’s posse never lost the sheen of desirability for a certain demographic of men, even though they have been accused of some unsavoury activities.
One incident documented in the Sales profile involves actress Elizabeth Berkley ignoring repeated invites to join the posse’s table at a nightclub as she was already with her boyfriend. When confronted on this by Berkley’s boyfriend Roger Wilson, posse member Jay R. Ferguson screamed homophobic slurs at him. This escalated into threats of a fight, with Leo reportedly overheard saying, “Let’s go kick his ass.” Before a fight could break out, someone punched Wilson in the larynx, causing permanent injury. His assailant was never found. Sales notes the panicked responses of the posse and Wilson’s assertion that “they were protecting him”. It’s not hard to piece together who they believe did the assault.
And then there’s Don’s Plum, a no-budget indie movie featuring DiCaprio and key Posse members Maguire and Connolly, directed by R.D. Robb. Originally intended as a short, the film was edited to feature length but prevented from a proper release by DiCaprio and Maguire, who sued the producer to keep it off screens, at least in North America. This was allegedly because some of the improvised dialogue was said to reveal personal experiences and tendencies of the pair that could dent their public images, which were on the rise following Titanic. The film’s now on YouTube, and it’s the kind of aimless indie film you’d see ten of at any given Sundance. It’s also really misogynistic, chock full of women being treated like objects and called “whores”. That seems like slim pickings in a decade where we saw Leo get an Oscar nomination for playing a drugged up wife beater who snorts cocaine out of women’s arseholes, but the lo-fi casualness of Don’s Plum is easy to define as real for this posse, so perhaps that’s why the pair fought so hard to stop people from seeing it.
All of that makes Swift’s own dealings rather frivolous by comparison. She’s a mean girl, not a douche bro, and the limits for each are very different. Yet where Leo fights to keep his posse out of the headlines, Swift is savvy in keeping hers front page friendly. Few celebrities manage their image with such precision as she does, and you can see that in how she engineers her squad’s social media presence. She knows when to call the paparazzi, but sometimes the personal touch is best. Look at the Summer of Hiddleswift. We all remember the tank-top and ocean frolicking, but remember that holiday was a 4th of July celebration. Everyone’s Instagram photos were released within quick succession of one another, revealing the super coolest red, white and blue weekend of patriotic prettiness you could imagine: Tom Hiddleston leading a bevvy of blonde beauties down a waterslide; the carefully arranged series of Polaroids revealing Swift and Hiddleston’s kiss; A trio of models in matching striped bikinis waving the flag in practiced poise. It’s fun by way of a military procession. If people bought for one moment that Hiddleswift was real - and it hadn’t all come during the glorious Kimye Snapchat spill - then it would have been mightily effective work. As it was, the veil slipped, as evidenced by Ryan Reynolds breaking the rules in one Instagram shot by hinting at bafflement over the entire performance.
The 1989 era saw the peak of #SquadGoals. Everyone wanted or needed a squad, and a vague gathering of pretty people or things in one space inspired hashtag frenzies. Patrick Stewart and Ian McKellen were Squad Goals. The cover of the Hollywood Reporter’s actress roundtable was Squad Goals. Burger King’s meal deal was Squad Goals. Friendship became an aim, a sign of status and something to inspire envy. For Swift, that worked well when she needed it to, but things are a lot quieter now, and different things are expected of her. Many criticised her for her suspect silence during the 2016 Election and a weak token tweet for the Women’s March (contrast that with Kim Kardashian, so often pitched as the “whore” to Swift’s “Madonna” in that insidious complex, who endorsed Hillary Clinton, fundraised for Planned Parenthood and has become the most famous opponent to deniers of the Armenian Genocide). The Hiddleston romance did nothing to quench claims of her inauthenticity, and even she seemed aware of her being overexposed, and so she took a step back. Bye bye to the Squad, and some of those former members felt no need to cry loyalty.
Kendall Jenner, obviously siding with her sister, insisted she was never really a member of the Squad; Most of them only seemed part of the picture when the picture looked good, and Lorde remarked (a tad insensitively, as she herself admitted) upon the unglamorous limitations a splashy celeb friendship has, although she claimed this had nothing to do with Swift. Some still rush to her defence, like Ruby Rose taking a swing at Katy Perry, whose own attempt to respond to Bad Blood fell flat. Swift is said to be working on a new album, which may bring with it a bright new wave of public friendship. In an interview with Vogue, she remarked that the best way to respond to press criticisms was to simply live your life, stating, “If the rumor is that you have fake friendships, all you have to do is continue to be there for each other.” Whether or not she chooses to publicise that is another matter.
As for the Pussy Posse, it lives on, but it cannot fight time. They seem to get together for special nights (and Leo remains the shielded one), and new members swirl around the epicentre, like Orlando Bloom and Jonah Hill, but this isn’t a dynamic of coolness and attainability that can retain its edge when its members are pushing 40. Some grew up, got married, had kids, got divorced. DiCaprio has begun to look like the holdout, with his assembly line of girlfriends always stopping at the age of 25. When even the golden bachelor of Hollywood chooses to marry up and have twins, DiCaprio becomes the true heir to Jack Nicholson, with whom he was often compared as a rising star. His dating habits inspire eyerolls, but he smartly keeps out of the press unless it’s for a film, his environmental activism, or getting that damn Oscar. His between-projects dadbod and vaping men inspire giggles but not cruel ones - he’s still too likeable for that, despite it all. The last of the Pussy Posse standing will always be the one who stayed on top.