20 Things You Didn’t Know About Leonardo DiCaprio’s '90s Boy Gang

In the ‘90s Leonardo DiCaprio got into all sorts of trouble with his entourage of young, up-and-coming actors. This is their story.

Once upon a time, Leonardo DiCaprio was a fringe child actor known for his precocious performances in indies like This Boy’s Life, The Basketball Diaries, and What’s Eating Gilbert Grape. Then that little scamp boarded the Titanic and became the King of the World.

When DiCaprio became a bona fide heartthrob for drawing Kate Winslet like one of his French girls, he was officially a grown man of 23. But something happens to a person who has had a job since the age of 5. Their transition into adulthood is corrupted. Leo was suddenly the most desired young actor in Hollywood, with piles of disposable income. He surrounded himself with a posse of other young male actors. Though they were at various stages of success, they shared their fierce loyalty to Leo and a penchant for going buck wild.

Nancy Jo Sales introduced Leo’s boy gang to the world via 1998’s “Leo, Prince of the City”. The now legendary NY Mag piece details some of their more infamous antics. The internet is rife with the finer points of their often-horrifying shenanigans. This list covers the most egregious moments of their privileged antics.

Here are 20 Things You Didn’t Know About Leonardo DiCaprio’s '90s Boy Gang.

20 The Members

Leonardo DiCaprio was the undisputed leader of the group. It simply wouldn’t have existed without him. The others basked in his glory and took advantage of the many perks that came with being a hot young movie star. The inner circle consisted of actor Tobey Maguire (freshly dusted with buzz from The Ice Storm), magician David Blaine, director Harmony Korine, and actors Kevin Connolly, Jay R. Ferguson, and Lukas Haas. Tertiary members included director R.D. Robb, and actors Josh Miller, Ethan Suplee, Scott Bloom, and Justin Herwick.

Together, they wreaked havoc on NYC society, binge drinking, pulling pranks, and chasing skirts. The Posse was young, dumb, and full of comely charm. Their notorious womanizing even earned a vulgar nickname for their "Posse."

19 Tobey Maguire Was Leo’s Right-Hand Man

Though David Blaine and Kevin Connolly were almost always in the mix, Leonardo DiCaprio’s first mate was Tobey Maguire. When they met as pre-teens, Leo liked the cut of Maguire’s jib so much that he tapped him for BFF status. In 2014, Leo recounted their meeting to Esquire. “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.”

They met at an audition and bonded over their burgeoning careers and single mothers. Not that it was hard for Leo to make friends. In the same interview, DiCaprio stated, “When I want someone to be my friend, I just make them my friend.”

18 The Unofficial Female Member

Though the Posse was a boy’s club, Leonardo DiCaprio recruited Sara Gilbert as the female ambassador. They met when Leo landed the prestigious role of “Darlene’s Classmate” on Roseanne. In the NY Mag article, Sales quoted an anonymous actor, who compared Gilbert to Shirley MacLaine in the Rat Pack. She was deemed cool enough to “hang with the boys” without creating any romantic tension or putting a damper on their antics.

Though she didn’t come out publicly until 2010, The Talk host discovered her preference for the ladies while dating her Roseanne co-star, Johnny Galecki. At the time, her orientation was an open secret in Hollywood, and something she could share with the other members of the Posse.

Gilbert doesn’t feature in any of their more infamous escapades, so that hopefully means her presence had a positive influence on them.

17 They Were Hoodlums

An anonymous early '90s director noted that, though Leonardo DiCaprio behaved himself when he worked in L.A., he and his pals would get up to all sorts of tomfoolery in the Big Apple. "They used to set off stink bombs at Sky Bar. But Leo's not going to act up [in LA] now. Anyone [in the movie industry] could be sitting at the next table. No one in the industry cares what he does in New York."

Leo’s pals were always eager for opportunities to show their loyalty to their leader. Paparazzo John Barrett recalls, “They get off on protecting him - they're always ready to start yelling and swinging." Other paparazzi claimed that Leo pelted them with grapes from his Mercer Hotel window.

The New York Post reported that he was spotted throwing garbage off the Brooklyn Promenade, “before speeding away in his chauffeur-driven Mercedes."

16 They Hounded Elizabeth Berkeley

The lads were accustomed to getting what they wanted, and didn’t take rejection well. When Showgirls' Elizabeth Berkeley declined to join Leonardo DiCaprio and Jay R. Ferguson for dinner, they reportedly harassed her by phone. Then they allegedly recruited L.A. publicist Karen Tenzer to “get” Berkeley by any means necessary, including repeated phone calls. Berkeley’s boyfriend, Roger Wilson, asked them to kindly knock it off. Instead, they swore at him and goaded him into meeting them at their hotel.

After a verbal confrontation, a still unidentified member of the crew reportedly punched Wilson in the throat, irreparably damaging his larynx. There are numerous shady details surrounding the incident. A hotel employee was fired after testifying against the Posse and the judge threw out Wilson’s $45 million lawsuit against DiCaprio. All this because Elizabeth Berkeley refused their advances?

15 Leo Allegedly Propositioned A Reporter

One remarkable aspect of the Sales piece is that she manages to paint a vivid picture of the Posse without ever interviewing Leonardo DiCaprio. Though Sales made repeated efforts to meet up with Leo, he never returned her calls. At least not officially.

Sales wrote, “One night when I got home after looking for Leo, there was a message on my answering machine. A group of young guys - they all sounded drunk - were laughing and cutting up in the background. It was kind of strange. The speaker was telling me that if I wanted an interview with him, I'd have to ‘make a deal’ along the lines of doing something for him that Monica did for Bill. ‘Then maybe we'll talk!’ he laughed.”

14 They Came Up Together

Leonardo DiCaprio’s entourage would agree that he is biggest celebrity of the bunch. But they all knew Leo before he was a major movie star. The young actors frequently ran into each other at auditions, where they were competing for the same roles.

Sales quotes an actor friend of theirs in NY Mag, “They were always betting on who would blow up first… Tobey was into more of a Tom Hanks track. Leo was modeling his career after Nicholson and De Niro." In the 1997 biography, The Leonardo DiCaprio Album, the actor expressed a preference for more dynamic roles, saying, "Portraying emotionally ill characters gives me the chance to really act."

Though they all got work, Leo’s was the one who got to work with legends like Robert De Niro and Johnny Depp. The Posse were peers, but also competitors, and eventually Leo rose to the top.

13 Kevin Connolly Pretty Much Plays Himself On Entourage

The hit HBO show Entourage is based on Mark Wahlberg’s real-life group of friends. Kevin Connolly’s character, Eric “E” Murphy is a composite of Marky Mark’s longtime assistant and his manager.

Wahlberg knew that Connolly would be perfect for E, because they met on the set of 1995’s The Basketball Diaries. Connolly wasn’t in the movie. He was there as part of star Leonardo DiCaprio’s real-life entourage.

What’s more, Jeremy Piven claims he improvised his most famous Ari Gold line as a way to get Connolly’s goat. Because Connolly doesn’t like to be touched, Piven “thought it would be very unsettling to hug him, and so it just kind of happened." Fans loved the interaction, and “Let’s hug it out, b***h” became the show’s standout line.

12 Harmony Korine tried to rob Meryl Streep

Harmony Korine mined his own troubled life for his 1995 screenplay Kids. But becoming a successful filmmaker wasn’t enough to break him of old habits. In 1998, Korine was scheduled for his fourth appearance on The Late Show. but he never made it to air. David Letterman declared that Korine was henceforth banned from the show but declined further comment.

In 2013, Spring Breakers star James Franco brought up Korine’s ban during his Letterman interview, saying he’d heard it was for pushing Meryl Streep backstage. That’s when Dave told the whole story.

"I went upstairs to greet Meryl Streep and welcome her to the show, and I knock on the door...and she was not in there. And I looked around… and I found Harmony going through her purse… And so I said, 'That's it, put her things back in her bag and then get out.'"

11 They Loved to Brawl

Violence seemed to follow the Posse everywhere they went. Of course, there’s the Elizabeth Berkeley incident incited by Leonardo DiCaprio and Jay R. Ferguson. But paparazzo John Barrett told Sales that Leo’s unofficial bodyguards were also keen to protect their boy from anyone they thought was infringing on his carefree lifestyle. “’They were rushing me outside Moomba’ on the night of James Toback's after-party for the premiere of Two Girls and a Guy, says the photographer, sighing, "’Here I am at my age dealing with a pack of little brats like that.’”

Trouble would find them even if they weren’t looking for it. In 2005, model Aretha Wilson attacked Leo at a party with a broken beer bottle. Wilson’s attorney argued that she was acting in self-defense after Leo took a swing at her for calling his crew, “a bunch of f***.”

10 They Refused To Tip

Despite his vast fortune, Leonardo DiCaprio calls himself, “the cheapest b*****d in the world… You never know, I may go bankrupt, or lose my career, or have a Hugh Grant situation." Just to be on the safe side, Leo stopped carrying money altogether, and “let” his friends pick up the tab.

In the Sales piece, a French bartender from one of their favorite haunts complained, “He does not [tip]! He gets his friends go to the bar for his drinks. He was in here with Julie Delpy -- I could not understand it. She's a very nice girl -- French. He is cheap.”

Sales tracked the Posse to “Ten's, the strip club on West 21st Street. I just missed them, but a dancer whispered hotly in my ear: 'He comes in here with all his friends and sits back like the Mack Daddy -- he doesn't even tip!'"

9 They Sabotaged Their Own Movie

Don’s Plum is one of those “lost films” of legend. Directed by R.D. Robb and shot in black and white, it was designed as an indie comedy akin to Clerks and Slacker. It starred many Posse members - including Leonardo DiCaprio, Tobey Maguire, and Kevin Connolly - as wise-cracking, foul-mouthed lotharios who drank coffee and compared romantic conquests.

Those who have managed to see it report that the mostly ad-libbed dialogue is often more tedious than offensive. Nonetheless, DiCaprio and Maguire didn’t want it released. Producer David Stutman filed a $10 million lawsuit on Maguire’s behalf, on the grounds that, "improvisational comments [Maguire] had made during the Film revealed personal experiences or tendencies that would undermine his public image."

Don’s Plum was pulled from Sundance, Miramax rescinded their investment offer, and Robb was banished from the Posse.

8 Their Antics Cost Them Jobs

In the early days, the crew wound up at the same auditions. According to one of Sales’ sources, Haas, who was a rising star from the age of 8 due to his role in Witness, lost two roles to DiCaprio: This Boy's Life and What's Eating Gilbert Grape. Leo scored a Best Supporting Actor nomination for Gilbert Grape.

Coincidentally, Haas also appeared in supporting roles in Inception and The Revenant, two DiCaprio-starring films. Leo famously earned his first Oscar for The Revenant.

Leo continued to land the best parts while his friends seemed relegated to his supporting cast instead of forging their own careers. Said Sales’ source, "All they do now is hang out with Leo… The people closest to him have Leomania worse than anyone.”

7 Tobey Maguire Is Keeping The Dream Alive

For a while, it seemed that Tobey Maguire settled into his role as a family man, raising 2 kids with Jennifer Meyer. But in 2015, the Spider-Man star filed for divorce from his wife of 9 years, and was soon back on the prowl. Some say Maguire never really gave up the Posse lifestyle.

Aaron Sorkin claims the antagonist of Molly’s Game is an amalgamation of poorly behaved celebrities from underground high-stakes poker tournaments. Readers of Molly Bloom’s memoir know that Maguire is responsible for many of Player X’s transgressions.

In a head-to-head hand, Maguire bluffed by swearing on his mother life that he held losing cards. After his opponent folded, Maguire rubbed in his victory by unnecessarily revealing his deception. Maguire also asked Bloom to “bark like a seal who wants a fish” in order to “earn” a $1000 poker chip. (She refused.)

6 Leo Is "Winning”

It probably comes as no surprise that though the Posse used their womanizing as a source of friendly competition, Leonardo DiCaprio has always held a commanding lead.

While promoting the Entourage movie, Kevin Connolly appeared on Watch What Happens Live. Host Andy Cohen who named Connolly as a member of the Posse, alongside Leo and Tobey Maguire, asked Kevin, “who got the most [women].” While a flustered Connolly took umbrage with Cohen using their infamous nickname, co-star Kevin Dillon quipped, “but the answer is Leo.”

Connolly agreed stammering, “…Yeah! I mean, the [NY Mag] article was written about him. We… you know… We got thrown into it but… It was just weird because we never… we never called ourselves that. But I mean, that answer is probably pretty obvious.”

5 They Want To Sell You A Mattress

If you’re going to be the “winner” of a skirt-chasing competition, you’re going to need a comfortable mattress. In 2015, Leonardo DiCaprio joined Tobey Maguire, singer Adam Levine, and Justin Bieber’s Manager Scooter Braun to invest in Casper Sleep Inc.

The flourishing e-commerce start-up is known for their quick and convenient mattress delivery. Car-less residents of New York City could order a comfortable “bed in a box”, which would be delivered within a matter of hours via bicycle or Uber. You never know when you’re going to have a mattress emergency.

The celebrity investors loved the business model and became part of a of $55 million investment that took the company to new heights. In 2017, Target offered to buy Caspar Sleep Inc. for $1 billion. Instead, Casper held on to the company, but took $75 million from Target to allow them the privilege of selling the mattresses.

4 There Were Rumors Leo Was Overcompensating

At one point, Sales’ NY Mag article suggests that perhaps Leonardo DiCaprio was motivated to bed as many ladies as possible in order to draw attention away from his secret desire for men. She wondered if the Posse members were really keeping their bro-ing platonic.

“And yet DiCaprio still can't seem to shake the rumor he's less than interested in the company of women. ‘If I want to go to a party with a few male friends, it doesn't mean I'm gay!’ Leo has said.”

Sales insinuated that one of Leo’s public relationships was little more than a P.R. stunt. Star reported that Leo had “fallen hard for a stunning young model,” while those close to DiCaprio said the affair was fabricated.

3 A Journalist Invented Their Name

During Kevin Connolly’s promotion for the Entourage movie, interviewers repeatedly brought up the thematic link between his character and his real-life affiliation with Leonardo DiCaprio’s Posse. A fed-up Connolly took the opportunity to dispel the rumors once and for all – not about the Posse’s antics, but about their name.

Connolly told The Daily Beast, “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 infamous name]. 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… But it was a good time.”

2 They’ve Re-Branded

What title does Leonardo DiCaprio’s merry band of gentlemen prefer? In 2016, fresh off his Best Actor Oscar win for The Revenant, DiCaprio partied with his long-time pals, including Lukas Haas and Tobey Maguire. They took the opportunity of public scrutiny to re-brand. One witness reported that in between “puffs of [Leo’s] vaping pipe,” the gang were “literally howling like wolves all night. They kept chanting, ‘’Wolf Pack, Wolf Pack, Wolf Pack!’”

As if to prove the new name was no flight of fancy, DiCaprio and four other members of the Posse donned Wolfman costumes to George Clooney’s Halloween party later that year. Maguire went his own way with a Monkey mask.

The Wolf Pack may have even adopted a mascot in the form of new recruit Orlando Bloom’s toy poodle, Mighty.

1 They’ve Grown Up (Sort Of)

While Leonardo DiCaprio is still keeping the dream alive by staying child-free and maintaining a steady influx of twenty-something model girlfriends, the other members of the Wolf Pack have taken a stab at settling down. Some have even stuck with it!

Tobey Maguire’s 9-year marriage produced 2 kids. Jay R. Ferguson and Ethan Suplee are also family men. Harmony Korine is married. David Blaine has been dating the same French supermodel (Alizee Guinochet) for 10 years. Leo might not have kids, but he tries to give back to the world through his environmental awareness contributions.

The Wolf Pack still meet up on a regular basis. Sometimes it’s fight night in Vegas. Other times, they take in an elementary school play.


Do you have any other crazy stories about Leonardo DiCaprio’s Posse? Tell us in the comments!

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