Skip to content, or skip to search.

Skip to content, or skip to search.

Leo, Prince of the City

The hottest young actor in America and his rowdy friends have made nighttime New York their playground, creating havoc and leaving in their wake a trail of awestruck fans (and often, no tip).


Hi Leonardo! You just seem to drain all my worries out of me when I'm watching one of your movies. You are a hell of a better actor than Brad Pitt and all those other shitty actors that some girls love to death. All I want to say before I sign off is that I don't think you are gay or bi and when some of my friends say they don't like you I am not ashamed to say that I am deeply in love with you. (Oh, and by the way, I'm a Calvin Kline sic model and I'm 21 years old!)
-- posted on the "Leonardo DiCaprio Is a Hot Babe!" Website, May 31

The furtive typing of teens in the Heartland is only the rawest expression of the global passion focused on the 23-year-old Hollywood actor Leonardo DiCaprio (named after Da Vinci, and with a Mona Lisa smile). What can Leo's life be like at the center of this raging obsession? I went looking for Leo to find out -- on the town in New York, where he can still be found most nights, as always, having a hell of a time.

I didn't find Leo at Jet 19, reportedly one of his hangouts, but I did meet a stockbroker named Ted who said he'd seen Leo at the Bubble Lounge recently. "I literally bumped into him," said Ted, laughing modestly. "I made a big impression on him."

Leo is six feet tall, according to the best-selling Leonardo DiCaprio, Modern-Day Romeo -- Ted is five foot three. But he was wearing a very expensive suit. "I know if he saw me again, he'd remember me," he said, convinced. "I was like, 'Yo, Leo, dude, whassup?' And he was, like, sooo down-to-earth. We talked about chicks, y'know? He was just a regular guy, sipping Stoli-and-soda. Talking about chicks." Again he gave a dry little laugh.

At Shine, the hot new club on West Broadway -- so hot, Leo goes there -- I met a slinky 40-year-old woman in false eyelashes who was dancing with a 24-year-old man. She told me, "I will have him, one day. I will see him here, and he will make eye contact with me, and he will know that we were meant to be together for a brief affair. Because he is so sensitive."

The actress Susan Sarandon, who lives in New York, recently pushed her way through hordes of Leomaniacs at the premiere of The Man in the Iron Mask to get an audience with DiCaprio for her teenage daughter, Eva, and seven of her closest school friends. "He was totally adorable," said Sarandon. "I humiliated myself."

Leo's been making the scene in New York for so long, he was already becoming a sort of tourist attraction, like South Street Seaport; but it was never anything like it is now. "I remember him and Juliette Lewis outside a Saturday Night Live party at Rockefeller Center a few years ago, begging the clipboard troll-ettes, 'Come on, please let us in,' " gossip columnist Anita Sarko says. "Even at the Basketball Diaries party at the Hard Rock Cafe, no one was paying much attention to him."

But then came the billion-dollar-grossing movie, the 500 Leo Websites, the plethora of hype and the attentions of the rich and powerful ("Leonardo DiCaprio . . . is an androgynous wimp," Senator John McCain grumbled recently), and Leo turned into "Leo." Now, venturing out at night with him feels like climbing onto the set of the Jerry Springer Show, says one of his close friends. "When he goes to a club, people start screaming and jumping over the security guards and elbowing and pushing to get near him."

And that's not just the civilians. "The models are all over him," says Jeffrey Jah, director of the club Life. "He's got rock stars, Puff Daddy, Donald Trump, going over to his table to sit with him. Leo just comes in to hang out with his friends."

Jah adds, "They never act up in here."

The Posse

"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.

The group's core members constitute a frat house of young men, some of whom are actually famous, like Leo. There's Lukas Haas, who has not yet become Leo, and Tobey Maguire -- the pensive youth in The Ice Storm -- who is, perhaps, waiting to. There's Harmony Korine, the Gummo boy auteur, and David Blaine, the levitating magician, who was recently spotted zipping around town on his new motorcycle with Leo -- they hit Moomba, Chaos, Veruka, and NV, where Mariah Carey had to wait in line to get a meeting. "I have fun with him, that's for sure," Leo said of Blaine two years ago when I was doing a story on the magician. "He'll do some pretty fucking crazy things. He's like a monkey with electrodes stuck to his head!"

And then there are the other guys in Leo's pack, who make up a kind of former-child-actor brigade: There's Jay Ferguson, once Burt Reynolds's wisecracking son on Evening Shade; Josh Miller, who played Keanu Reeves's little brother in River's Edge but never became Keanu Reeves; Ethan Suplee, who appeared briefly in Chasing Amy; Kevin Connelly, who has appeared on the WB; Scott Bloom, another aspiring actor; Justin Herwick, with whom Leo almost got himself killed over the California desert in 1996, when his parachute failed to open (his instructor released an emergency cord). The Leo men seem to like to play rough. "I like to do things that scare me," said DiCaprio.

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. "A lot of them have known each other a long time; they started out as child stars together." (That was back in Leo's Growing Pains days, during which "he was becoming a bit of a misfit in his classes," the best-selling Leonardo DiCaprio, Romantic Hero reports gently. "Leonardo alarmed his teachers . . . when he drew a swastika on his head as part of his improvised imitation of mass murderer Charles Manson.")

The posse "used to see each other at auditions all the time," says their young actor friend, "and a little competition rose up between them." In fact, Haas lost out twice to DiCaprio for plum roles -- in This Boy's Life and What's Eating Gilbert Grape, for which DiCaprio won a Best Supporting Actor nomination. ("Why should I want to be him?" Haas snapped to Texas Monthly in 1996.)

Current Issue
Subscribe to New York

Give a Gift