Contact Us

‘The ‘Pussy Posse': Leonardo DiCaprio’s Other Hollywood Legacy

Vivien Killilea, Getty Images
Vivien Killilea, Getty Images

The 88th Annual Academy Awards are this Sunday, February 28, and Leonardo DiCaprio is heavily favored to nab Best Performance By an Actor In a Leading Role for The Revenant. DiCaprio earned his first Oscar nomination back in 1994 as Johnny Depp’s mentally-disabled brother in What’s Eating Gilbert Grape, and a win would end his past “always the bridesmaid, never the bride” streak of five nominations and zero wins. But as deserving of a gold statue as he may be, the accolade is just one way to measure Leo’s decades-long impact as a Hollywood figure.

Sure, an Oscar would be the cherry atop the sundae that is his celebrated career; one that boasts a flawless transition from child actor to leading man. But we’re not here to discuss how good Leo was in The Aviator — we’re here to revisit the headiest days of his life as a serial modelizer, when he was the brightest star in a constellation of hard partying New York City skirt-chasers dubiously nicknamed the “Pussy Posse.”

#Friday vibin with the #pussyPosse

A photo posted by Alex Nuñez La Tigresa (@shockingly_unambitious) on

What’s the Pussy Posse?
While there’s no way to trace who originally coined the phrase, Nancy Jo Sales used the term in her 1998 New York magazine story “Leo, Prince of the City.”

“They” are the fun-lovin’ guys you always see Leo around with. Even before there was Leomania, Leo always traveled with his pack of devotees, known in Hollywood circles as “The Pussy Posse.” “They’re all about seeing the girls,” says a magazine photographer in New York who once had to sneak Leo and his boys, then the uninvited, into a Victoria’s Secret event.

Like Frank Sinatra’s Rat Pack, or Molly Ringwald’s ’80s-era Brat Pack AND Ben Stiller and Owen Wilson’s late ’90s Frat Pack, DiCaprio met most of his cohorts on the job, and their boozy nighttime exploits kept their names in the gossip pages. Sales’ piece is considered the definitive Pussy Posse profile and it’s an all-around fascinating and funny read, peppered with contextually-ironic quotes from teenybopper-facing biographies like Leonardo DiCaprio, Modern-Day Romeo. It chronicles a time in the late ’90s when DiCaprio discovered the joys of NYC after shooting The Basketball Diaries there in 1994. These were the days before social media, when high-profile bad behavior was far less documentable.

“New York is like Leo’s playground, his Disneyland,” says an aspiring director who says he’s frequented strip joints with Leo’s posse in L.A. “They used to set off stink bombs at Sky Bar. But Leo’s not going to act up out here now. Anyone in the of course, movie industry could be sitting at the next table. No one in the industry cares what he does in New York.”

"They're saying WHAT about me on Twitter?? After I won!? Man, whatever." #pussyposse

A photo posted by Carlos Herrera (@herreracarlos) on

Most of the exploits reported in the press were fairly pedestrian. Aside from repeated references to Leo’s alleged cheapness — “He does not teep!,” insists a French bartender at NYC then-hot spot Spy, “Leo’s cheap,” his own friend Ethan Suplee says bluntly — it was standard-issue hedonism involving strip clubs, bottles ‘n models, and dumb mischief: Bombarding paparazzi with grapes, throwing litter onto cars on the Brooklyn Queens Expressway from above. But Sales reports an incident involving Saved By the Bell‘s Elizabeth Berkeley and her then-boyfriend Roger Wilson that ended in a well-documented scuffle, and suggests the Pussy Posse didn’t react well in the rare event their wants weren’t met (in this case, what they wanted was attention from Elizabeth Berkeley). You can watch a 1998 Extra story on the alleged assault on Wilson here.

Who Was the Pussy Posse?

The group’s core members constitute a frat house of young men, some of whom are actually famous, like Leo.

Sales’ New York profile illuminates a larger truth about celebrity networks’ interconnectedness: It’s a micro view of the many labyrinthine ways stars know each other, both pre- and post-fame — often from starting out in the biz young together, attending the same auditions, being the child of industry folks and/or attending the same schools. At the time of Sales’ article, Titanic had just hurled Leo’s fame into the stratosphere, while his up-and-coming friends had either plateaued or hit a downward trajectory. And so, the article suggests, some siphoned the glory.

“All they do now is hang out with Leo,” an unnamed actor told Sales. “If Leo wants to go to Paris, it’s let’s go to Paris. Las Vegas? No problem.” Sales’ various sources claim the non-Leo Posse members acted as unofficial bodyguards on movie sets and even held his money for him during group trips. “The people closest to him have Leomania worse than anyone,” the actor said.

Some of the group’s members went on to become more recognizable than they were in the Pussy Posse days; others less so. Here’s a quick review of key members, and where they’ve been since.

Tobey Maguire: Tobey and Leo were pals from boyhood (see above). The Spider-Man actor was, and remains, the most consistently-famous member of the Posse.

Lukas Haas: Also a former child actor, Sales notes that Haas “lost out twice to DiCaprio for plum roles — in This Boy’s Life and What’s Eating Gilbert Grape.” Perhaps his also-ran status, in addition to his talent (watch the movie Brick, if you haven’t) is what’s earned him parts in more recent DiCaprio vehicles Inception and The Revenant.

Kevin Connolly: Yes, he was an actual entourage member before Entourage. Hollywood is so meta.

Jay Ferguson: Painted as the main instigator in the above-mentioned Elizabeth Berkely fracas, fans of Mad Men will recognize the former child actor as Stan Rizzo.

Sara Gilbert: The former Roseanne star met Leo on the set of Poison Ivy. “If they’re a new Rat Pack, she’s the Shirley MacLaine figure,” Sales anonymous actor source said. Gilbert. The actress and The Talk personality is married to 4 Non Blonde singer Linda Perry, which is the ’90s-est couple that ever ’90s-ed.

Harmony Korine: Screenwriter of Kids and Gummo, director of Spring Breakers, NYC mid-90s cool kid.

David Blaine: The New York street magician who rose to national prominence with TV specials (featuring Leo) and a lot of uncomfortable performance art-y “tricks” in NYC during the mid ’00s. He also dated Fiona Apple. “I have fun with him, that’s for sure,” Leo told Nancy Jo Sales for an earlier Blaine profile. “He’ll do some pretty f—king crazy things. He’s like a monkey with electrodes stuck to his head!”

Q-Tip: The most famous member of Tribe Called Quest, the Queens hip hop group that broke up for the first time in 1998.

Ethan Suplee: That one guy from My Name Is Earl! You know the one.

Justin Herwick, Josh Miller and Scott Bloom: You, uh, haven’t heard of them.

David Rappaport, Leonardo DiCaprio, A Tribe Called Quest, Busta Rhymes and Harmony Korine in the '90s.  (via Tumblr, @goodfiends)
Michael Rapaport, Leonardo DiCaprio, A Tribe Called Quest, Busta Rhymes and Harmony Korine in the ’90s. (via Tumblr, @goodfiends)

DiCaprio’s formidable body of work has eclipsed his extra-curricular adventures in the 18 years since the New York‘s investigation, though he’s remained close with several core Pussy Posse members: The photo at the top of this post was taken at a 2012 release party for Mobli, an app that DiCaprio, Maguire and several other pals invested in. Time has mellowed Leo’s squad — while he’s still known for being quite the active bachelor about town(s), grownups don’t have a ton of time to get drunk and throw trash onto traffic. But reports of his Pussy Posse days are a densely-packed time capsule, showing us the ’90s, a celebrity culture in which stars were unencumbered by gawker’s smartphone cameras (and Gawker the website), and a time when people accepted a moniker a gross as “the Pussy Posse” and still liked Leo anyway.

 

Next: Leonardo DiCaprio + Dame Maggie Smith Smooch for Kiss Cam

Recommended for You

Best of the Web

Best of PopCrush

Leave a Comment

It appears that you already have an account created within our VIP network of sites on . To keep your personal information safe, we need to verify that it's really you. To activate your account, please confirm your password. When you have confirmed your password, you will be able to log in through Facebook on both sites.

Forgot your password?

It appears that you already have an account on this site associated with . To connect your existing account just click on the account activation button below. You will maintain your existing VIP profile. After you do this, you will be able to always log in to http://popcrush.com using your original account information.

Please fill out the information below to help us provide you a better experience.

(Forgot your password?)

Not a member? Sign up here

Please solve this simple math problem to prove that you are a real person.

Sign up for PopCrush quickly by connecting your Facebook account. It's just as secure and no password to remember!