On Sunday night, Leonardo DiCaprio finally took home an Academy Award for Best Actor. Naturally, the post-show gaiety featured the sort of pomp and revelry befitting the wake of a storied meme. DiCaprio linked up with his actor pals Lukas Haas, Tobey Maguire, and Vincent Laresca for some old-fashioned ritualistic chanting. According to one lucky partygoer, “The crew was literally howling like wolves all night. They kept chanting, ‘Wolf Pack, Wolf Pack, Wolf Pack!’”

The 41-year-old’s merry band of brothers seems to be more bark than bite; after a few drinks and a handful of “puffs of his vaping pipe,” DiCaprio absconded with his shiny trophy and a bottle of champagne. This is a far cry from the ’90s, when a fresh-from-the-raft Leo rode T he Titanic to insta-celebrity status, flanked by his Wolf Pack—more famously known by their original moniker, “The Pussy Posse.”

To do The Pussy Posse justice, we must journey back to a prelapsarian, pre-recession New York City, where Leo and his friends hung out at clubs named after deadly sins and random textures, and Nancy Jo Sales wrote sentences like, “The fires of Leomania licked at my brain.” We speak, of course, of “Leo, Prince of the City,” Sales’s legendary 1998 New York profile of a young man and his devoted bros. Before we had Entourage, we had The Pussy Posse: Lukas Haas, Tobey Maguire, Harmony Korine, David Blaine, Jay Ferguson, Josh Miller, Ethan Suplee, Kevin Connolly, Scott Bloom, Justin Herwick, and occasionally Sara Gilbert—a patchwork quilt of aspiring actors and former child stars.

“I have read it,” Connolly told The Daily Beast of the New York mag piece. “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. 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.”

Native to L.A., The Pussy Posse ravaged NYC like an invading army, marching under the banner of “no homo.” According to Sales, Leo’s friends wanted to be with the star 24/7. They accompanied him to work, acted as “unofficial” (ineffective?) bodyguards, and even carried DiCaprio’s cash. When not acting as glorified man purses, The Pussy Posse unleashed stink bombs at Sky Bar, snuck into Victoria’s Secret events uninvited, took impromptu trips to Vegas, and haunted local clubs and strip joints. The fresh-faced connoisseurs of the Meatpacking District could be found throwing grapes at paparazzi from upstairs at the Mercer Hotel, or dropping trash off of the Brooklyn Promenade into the traffic below. Despite this slumber party, circle jerk mentality, DiCaprio insisted, “If I want to go to a party with a few male friends, it doesn’t mean I’m gay!”

All tea-sipping aside, The Pussy Posse quickly became notorious for treating women with more disrespect than a black teenager gets at a Donald Trump rally. On top of regular accusations of lecherous behavior, player mentalities, and a complete inability to tip strippers, Sales stumbled upon a few instances of outright misogyny. One of the most outrageous incidents involved Elizabeth Berkley, the Showgirls star, who made the grave mistake of walking into the VIP area for The Man in the Iron Mask premiere. Little did she know that she was entering the wolf’s den.

The Pussy Posse spotted Berkley in the crowd, and immediately sent L.A. publicist Karen Tenser over to scoop her up. “She said, ‘Jay Ferguson and Leo are going crazy for you, and they want you to come to Elaine’s after this.’” Berkley, who was dating actor Roger Wilson at the time, politely refused. Case closed, right? Not quite. Allegedly, Berkley was bombarded with calls from both Ferguson and Tenser, inviting her to dinner and out on the town. The harassment became so overwhelming that Wilson decided to step in: “I said, ‘Look, Jay… I know you guys are having a great time and the town is your apple—but not this part of town.’” After a pregnant pause, Ferguson responded, “Fuck you, you fuckin’ faggot motherfucker, we’ll call whoever we want and if you don’t fuckin’ like it, why don’t you come down here and tell us to our face?”

What followed was a surreal interaction at the ritzy restaurant Asia de Cuba in New York City, where The Pussy Posse was gathered at an appropriately dramatic supper. After Wilson arrived and took up Ferguson’s offer to “step outside,” DiCaprio reportedly added “let’s go kick his ass,” leading the Posse in a mass exodus. Someone punched a distracted Wilson in the Adam’s apple, damaging his larynx. Questioning the veracity of Wilson’s claims, one of Leo’s friends later insisted, “That girl would have come in a second if we’d wanted her to. Any girl would.”

Exhibit B is Don’s Plum, a low-budget movie starring, produced, written, and directed by The Posse. The divisive film pitted brother against brother, with producer David Stuntman eventually filing a suit against DiCaprio and Maguire, alleging that the actors used their fame and influence to block Miramax from distributing the film and dissuade the Sundance Film Festival from screening it. According to Stuntman’s lawsuit, “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.” In fact, that’s something of an understatement. In the heavily improvised film, the “public image” projected is one of outright debauchery. At one point, DiCaprio tells a crying girl to “Stop looking at me like that—I’ll fucking throw a bottle at your face, you goddamn whore.” Leonardo DiCaprio is now a nationally beloved Academy Award winner, and David Stuntman is an ex-member of The Pussy Posse.

Oh, and you can watch Don ’ s Plum on YouTube.

But the car crash appeal of The Pussy Posse wasn’t in their rampant misbehavior; it was in our shared fascination with celebrity friendship, and with man-on-man emotional connections. The Pussy Posse was more about pissing contests than pussy, as a tight-knit group of young, handsome competitors raced one another to the forefront of the Hollywood scene. In fact, The Posse might be one of the finest examples of “frenemy” culture in the modern era. Before we had Kim Kardashian passive-aggressively cleaning Paris Hilton’s closet, we had Lukas Haas losing two potentially star-making roles to DiCaprio in the ’90s, before snarkily telling Texas Monthly, “We’re both very lucky. Why should I want to be him?” While Leo’s rising star was the engine that kept his posse sharp, jealous, and mean, he was also the emotional glue that kept them together. Much like a young Regina George, DiCaprio groomed his group of hotties. He told Esquire, “When I want someone to be my friend, I just make them my friend.” When a 12-year-old DiCaprio spotted Maguire on set, “I literally jumped out of the car. I was like, ‘Tobey! Tobey! Hey! Hey! And he was like, ‘Oh, yeah—I know you. You’re… that guy.’ But I just made him my pal.”

These days, the squad formerly known as The Pussy Posse is having a midlife crisis. Tobey Maguire has kept up a steady career with films like Spider-Man and The Great Gatsby. While his celebrity has declined somewhat since the summit of Spider-Man, he’s happily married with two kids. Jay Ferguson of “possibly assaulted Elizabeth Berkley’s boyfriend” fame also has a happy family (and was Stan Rizzo on Mad Men!), as does Ethan Suplee. Harmony Korine is married, and seems to be keeping a low profile since gifting the world with Spring Breakers, an ode to jailbait in neon bikinis and James Franco in cornrows. Kevin Connolly, who truly did The Pussy Posse proud by starring in Entourage, seems incapable of escaping the name E. David Blaine is still a magician, which is still pretty embarrassing. As for Academy Award winner Leonardo DiCaprio, exclusively dating millennials appears to be the last remaining vestige of his Pussy Posse prowess. The actor’s gone from stiffing strippers to spending millions of dollars annually to promote environmental awareness. So while we respect the Posse’s rebranding push, it feels like The Wolf Pack is already on its last legs. Sorry, Leo—roving bands of former child stars are so 1998.