Leo's Pussy Posse in 2014: A Power Ranking

3. Harmony Korine

When Korine first started hanging out with DiCaprio in the late 90s, he was considered a scumcore darling and indie film wunderkind, having produced both Kids (which he wrote) and Gummo (which he wrote and directed) by the time he was 25.

Despite going through a rough patch where he struggled with drugs and was maybe caught stealing money from Meryl Streep during the early-aughts (and despite the fact that both Kids and Gummo are fucking terrible), Korine has managed to straighten his life out and continue his successful film career. He released Spring Breakers — one of the most controversial and talked about movies in recent memory — in spring of 2013.

4. Kevin Connolly

In the Pussy Posse heyday, Kevin Connolly was best known as A.) being a part of Leonardo DiCaprio’s entourage and B.) an actor on the WB show Unhappily Ever After. Now, for better or for worse (worse), he’s known for being a part of a fake actor’s entourage on the HBO series Entourage, a show that, despite ending 2011, remains impossible to forget. (If only we could be that lucky.)

Connolly will reprise his role as E when Entourage reemerges as a film in 2015.

In real life, Connolly continues to live up to the Pussy Posse name, having once gotten into an online kerfuffle where he called a girl ugly a bunch of times because he didn’t like what her Facebook friends were saying about him.

5. Jay R. Ferguson

Of all the horrible behavior allegedly committed by the Pussy Posse, Jay R. Ferguson’s came off as the worst. Not only would he not stop harassing actress Elizabeth Berkley, but he even went as far as to challenged her boyfriend Roger Wilson to a fight after Wilson stepped in and asked him to cut it out.

From “Leo, Prince of the City:”

“Really upset,” Berkley went to Wilson, who was in their living room watching sports. Hearing what had gone on, Wilson (who’s from Brooklyn) asked for Tenzer’s cell number and got Jay Ferguson on the phone. “I said, ‘Look, Jay,'” says Wilson, “‘I know you guys are having a great time and the town is your apple — but not this part of town. I don’t know how this got started, but I’m just asking you please not to call my home again, and Elizabeth has asked please that you not call her again. . . . Okay?'”

“And then I heard a lot of profanity,” says Berkley.

“There was a two-second pause,” Wilson says, “and then it’s, ‘Fuck you, you fuckin’ faggot, fuckin’ 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?'”

It escalates from there, with Wilson agreeing to go to the hotel where DiCaprio, Ferguson and several others were having dinner.

…According to a sworn statement reportedly given to police by the restaurant’s chief of security (who, three weeks later, was no longer employed there), DiCaprio said to the others at the table: “Let’s go kick his ass.” And the rest of the table… followed.

Wilson claims two hotel security guards stood on either side of DiCaprio, who was smoking a cigarette, as he and Ferguson squared off on the sidewalk outside the entrance. “I’m facing Jay Ferguson, two feet in front of me,” says Wilson. “The other guys are yelling at me, ‘Fuck you, faggot! Go home, you fuckin’ wimp, you’re pathetic.’ You know, all this.”

The altercation ended when an unidentified member of the entourage sucker-punched Wilson in the throat and permanently damaged his larynx. What a nice group of boys!

Ferguson wasn’t terribly famous at the time (he had appeared in The Outsiders and played Burt Reynolds’ son on the early 90s series Evening Shade), but despite all of his Elizabeth Berkley-harassing and ‘faggot’-slinging, he’s actually doing quite well for himself these days. He now plays the lovable stoner/copywriter Stan on Mad Men. Ugh, it’s always a bummer when a character who’s so cool is played by a person who is SO without.

6. Q-Tip

Musician and producer Q-Tip is still making albums although he is far less prolific now than he was at the height of the Pussy Posse’s reign. He is currently working on solo album “The Last Zulu” and producing Kanye’s next album alongside Rick Rubin.

Credit where credit’s due, Q-Tip has always been better known on his own and for his contributions to hip hop (he was in A Tribe Called Quest, for fuck’s sake) than he ever was as a member of the Pussy Posse. Still, once in the posse, always in the posse. (<—-Not true, as we'll later find out.)

7. David Blaine

David Blaine was well-known in the 1990s and is well-known now, but, unfortunately for him, the thing well-known for is being a magician and that carries about as much status as being a peddler of old rags.

8. Sara Gilbert

“An adjunct member of the pack is the heavy-haired Sara Gilbert of Roseanne, who was starring in Poison Ivy when Leo was just “Guy #1″ in the script. ‘If they’re a new Rat Pack, she’s the Shirley MacLaine figure,’ says a young actor who’s hung out with the crowd in L.A,” wrote Sales in her New York article.

Gilbert, though always most famous for her role as Darlene Conner, remains in the public eye. She’s a co-host and creator of CBS’ insufferable The Talk and was recently married to 4 Non Blonde’s Linda Perry!

9. Lukas Haas

Ah, poor Lukas! He so much potential circa 1998, what with his having starred in Boys, Everyone Says I Love You, Mars Attacks! and all, but things never really panned out for him the same way they panned out for his friends Leo and Tobey. Don’t get me wrong, he’s still working — rather frequently actually — but only in small roles and often in his more famous friends’ movies.

10. Ethan Suplee

Ethan Suplee is one of those actors who you probably can’t name, but most likely recognize. He’s appeared in multiple Kevin Smith movies, Boy Meets World, My Name Is Earl and, most recently, The Wolf of Wall Street.

He is also a devoted Scientologist.

11. Joshua John Miller

HE WAS THE LITTLE BROTHER IN TEEN WITCH. FOREVER IN OUR HEARTS <3<3<3

12. R.D. Robb

If you’ve never heard of R.D. Robb, that’s because the Pussy Posse doesn’t want you to know who R.D. Robb is. A young filmmaker and thriving member of the Posse in the late 90s, Robb directed Don’s Plum, an improvised film starring DiCaprio, Maguire and a bunch of other 22-year-olds sitting around and talking to each other in a restaurant. Oh, good — a movie about my personal hell.

Robb was blacklisted from the Posse after Maguire and DiCaprio sued to block the film’s release because Maguire was reportedly worried that “improvisational comments he had made during the Film revealed personal experiences or tendencies that would undermine his public image.”

One of DiCaprio’s more charming lines from the film: “Do you girls masturbate at all? Stop looking at me like that — I’ll fucking throw a bottle at your face, you goddamn whore.”

LET HIM DRAW YOU LIKE ONE OF HIS FRENCH GIRLS.

In 2014, you can watch all of Don’s Plum on YouTube. Be warned: Variety described it as an “unpleasant and tedious ensemble.”

Robb has fallen off the face of the Earth and — proving the reach of the Posse — all of his photos have been scrubbed from the internet. (JK, you can look at some here. Look! He was in A Christmas Story!)