Catching Up With Leonardo DiCaprio’s ’90s "P*ssy Posse"

At the height of his heartthrob fame, Leo was a notorious party monster. He kept a tight group of semi-celebrity guy friends who lived up to the filthy name they gave themselves.

1. The posse back in their heyday

David Blaine, Leonardo DiCaprio, Tobey Maguire. Click here for the NSFW nude version of this photo, which is probably photoshopped.

In the late ’90s, Titanic had just made Leonardo DiCaprio the most lusted-after heartthrob in the world, and he was enjoying all the rewards of his newfound fame and fortune. DiCaprio kept a close-knit group of guy friends that called themselves “the pussy posse,” named after their love of chasing girls and partying. They became New York City nightlife fixtures, with bad-boy behaviors like getting into fights, setting off stink bombs in nightclubs, and worst of all, being notoriously bad tippers to waitstaff.

A 1998 New York magazine article, “Leo, Prince of the City,” details the rumors of the posse’s exploits. It’s full of amazing moments, like Elizabeth Berkeley’s boyfriend trying to beat up one posse member who kept calling Berkeley and asking her to dinner and a quote by Sen. John McCain saying “Leonardo DiCaprio … is an androgynous wimp.” The article gets really crazy when the writer convinces a Leo look-alike to drive around Times Square in a limo, sending teen girls into a frenzy.

The posse was made up mostly of child actors who got to know one another growing up in L.A. and seeing each other at the same auditions — DiCaprio himself was a child actor before he hit it big. (The close male friendships stoked the fires of rumor that he was gay or bisexual for years, though it seems it was all just a bromance.)

The posse appears to have remained tight to this day, core members going to Lakers games and red carpets together. Several posse members keep popping up in DiCaprio’s films or working behind the scenes for his production company.

It appears the pussy posse didn’t break up; it just went legit.

Blaine, DiCaprio, Haas cavorting on the streets of New York.

5. Tobey Maguire

Lucas Jackson / Reuters

Maguire was already known for being a cute, quirky guy in movies like The Ice Storm. The posse thought of him as having the Tom Hanks–type career of the group — then the Spider-Man series made him a blockbuster star. Maguire’s married with kids now, and probably doesn’t indulge in the kind of carousing they used to do, but he’s still tight with his childhood friends.

This year, Maguire will be starring in Baz Lurhman’s The Great Gatsby as Nick Carraway alongside his old posse pal Leo as Jay Gatsby.

Maguire and DiCaprio as kids.

8. Lukas Haas

Alberto E. Rodriguez / Getty Images

According to the New York magazine story, Haas lost out several roles to DiCaprio, but they still remained close friends. Haas was sort of on the cusp of being a teen heartthrob back in the late ’90s when he starred in Boys with Winona Ryder. Let’s face it, though: He’s cute, but no Leo. Haas lived in DiCaprio’s house with him for seven years, until 2010 when DiCaprio’s then-girlfriend Bar Refaeli reportedly made him kick Haas out.

He has done some TV guest spots and low-budget horror movies, and in 2010 he had a role in Inception as DiCaprio’s old friend who betrays him.

10. Kevin Connolly

Dimitrios Kambouris / Getty Images

Connolly played the teenage son on the WB sitcom Unhappily Ever After during the posse’s reign from 1995–1999. He’s best known as E on HBO’s Entourage and for dating Nicki Hilton for several years. He’ll be in an upcoming Sylvester Stallone movie called Reach Me and a comedy called Elvis & Nixon.

Connolly and DiCaprio are often seen at Lakers games together.

12. David Blaine

Mike Coppola / Getty Images

David Blaine always seemed like the wild card in the group, the only one not involved in the movie business. But he was a New York City nightlife staple and always dated beautiful women, including Fiona Apple and Daryl Hannah. He continues to perform feats of endurance, his most recent one having been this summer, when he became a human Tesla coil.

Blaine had a baby in 2011 with his French model girlfriend, but on Jan. 18, 2012, TMZ caught him canoodling in a club with another woman. Blaine explained it was because he and his French model fiancée were “on a break.”

Blaine doesn’t appear at public events with DiCaprio and the old crew like Maguire, Haas, and Connolly do, but it’s possible they’re still friends.

14. The posse together again in March 2012

16. Harmony Korine

Alberto E. Rodriguez / Getty Images

Harmony Korine became an indie wunderkind after directing Gummo at age 24. His newest movie, Spring Breakers, starring Selena Gomez, Vanessa Hudgens, and James Franco, comes out this spring.

18. Joshua John Miller

John M. Heller / Getty Images

Miller was a child actor who played Keanu Reeves’ little brother in The River’s Edge. He attended Yale and UCLA, and in 2003 got a master’s in creative writing from the University of Iowa. Today, he keeps an active Twitter account and, guessing from his tweets about gay dating sites, he may not have been the most active pussy-chaser in the group.

20. Amber Benson

Frazer Harrison / Getty Images

A female adjunct posse member, Amber Benson starred in the ill-fated Don’s Plum alongside Maguire and DiCaprio. She is perhaps most recognizable as lesbian witch Tara on Buffy the Vampire Slayer.

This spring, Benson will star in fellow posse member Harmony Korine’s upcoming Spring Breakers.

22. Ethan Suplee

Frazer Harrison / Getty Images

Suplee is recognizable as Jason Lee’s buddy on the sitcom My Name Is Earl, though he’s lost over 200 pounds since the show ended. He’s also a Scientologist, just like Lee.

Suplee has a role in the upcoming DiCaprio film The Wolf of Wall Street.

24. Q-Tip

Frazer Harrison / Getty Images

Q-Tip was one of the few non-actors, along with David Blaine, in the posse. His music career may have cooled after the hit album Vibrant Thing, but he’s releasing an album this year called The Last Zulu, he performed at the BET Awards this year, and he does regular DJ gigs. He’s also acted in several movies, most recently Cadillac Records and Holy Rollers with Jesse Eisenberg.

26. Sara Gilbert

Phil Mccarten / Reuters

New York magazine’s source described Gilbert’s unlikely involvement in this boys’ club: “If they’re a new Rat Pack, she’s the Shirley MacLaine figure.” In 2010, Gilbert came out publicly as a lesbian and is now dating musician Linda Perry.

Gilbert created and executive produces the daytime talk show The Talk, which she currently appears on along with Julie Chen, Holly Robinson Peete, and Sharon Osbourne.

28. Jay R. Ferguson

Alberto E. Rodriguez / Getty Images

Ferguson was a child actor who starred as Burt Reynolds’ son on the 1990–1994 TV series Evening Shade. He’s continued to work in TV — you may recognize him best as macho copywriter Stan on Mad Men.

New York’s story describes in detail an alleged incident where Ferguson got into a fight with Elizabeth Berkeley’s boyfriend after repeatedly asking her to come meet him at the after-party for The Man in the Iron Mask. Berkeley kept declining, and eventually the boyfriend called Ferguson to tell him to stop pestering his girlfriend. Ferguson challenged him to come to the restaurant to fight, which he accepted. Ferguson, DiCaprio, and several other friends stepped outside, and someone — not Ferguson — sucker punched the boyfriend in the throat, permanently damaging his larynx.

30. R. D. Robb

Mike Guastella / Getty Images

Robb was a child actor in A Christmas Story, and he directed the film Don’s Plum, starring his posse pals Leo, Tobey Maguire, Kevin Connolly, Scott Bloom, and Amber Benson. The premise of the film was a group of friends talking about life and sex around a restaurant, with a lot of improvisational dialogue. Before it could be released, McGuire and DiCaprio sued to block the film’s release. According to reports gathered by New York magazine, Maguire was worried his misogynistic and foul-mouthed ad-libbing would damage his reputation, and got Leo to use his clout to have the film’s distribution dropped by Miramax. The film was never released in the U.S. and Canada, only abroad.

The movie also starred former chid actress Jenny Lewis and her Rilo Kiley bandmate/boyfriend Blake Sennett, also a former child actor, wrote the soundtrack. BuzzFeed’s Louis Pietzman once spotted Maguire in the crowd at a Rilo Kiley show a few years later. Either Maguire is just a fan, or Jenny Lewis has stayed part of the posse’s circle of friends.

Robb has had some indie production credits over the last few years, but it seems it has been hard to recover after being blacklisted from the posse.

32. Scott Bloom (far right)

Matt Carr / Getty Images

Scott Bloom played Alyssa Milano’s boyfriend on Who’s the Boss, and he also starred in the posse-centric film Don’s Plum, directed by R. D. Robb.

Bloom was a producer on Welcome to the Rileys, starring James Gandolfini and Kristen Stewart. He’s reportedly developing a movie version of the TV series The Twilight Zone for DiCaprio’s production company Appian Way.

Justin Herwick’s acting career never really took off; his most recent role was in 2002’s Luster. As a pal of Leo’s, he also had a credit as a production assistant on Romeo + Juliet. In 1996, DiCaprio and Herwick went skydiving together, and DiCaprio’s chute failed (the instructor he was tandem diving with saved him). Herwick told People magazine, “I thought I was going to lose my best friend.”

He was married from 2000–2002 to former Charles in Charge actress Nicole Eggert, and they have a daughter together with the creative name spelling Dilyn.

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