The Art of the Schmooze

“It’s really weird, because I do have a lot of friends who are famous, but I always knew them way

“It’s really weird, because I do have a lot of friends who are famous, but I always knew them way before,” said Jonathan Cheban on a recent evening at Nobu. “I mean, back in the day when Ozzy would play Madison Square Garden, I was sneaking Kelly and Jack into Suite 16. And I’ve been friends with Paris and Nicky since they were kids.”

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Jonathan Cheban looks familiar-too familiar. Biting on rock shrimp tempura, he absently ran a hand through his longish dark hair. He was casual but stylish in Levi’s, a long-sleeved gray T-shirt peeping out from under a collared navy Polo, his feet encased in black Louis Vuitton shoes. (“They’re like butter!”) Fellow diners nodded in his direction or shot him a curious glance. Maybe they recognized the 31-year-old New Jersey native from the glossy pages of Us Weekly or Star magazine, where he’s one of those anonymous types in the background of all the flash-heavy paparazzi shots, partying with Paris, snacking on sushi with Mischa. At the front rows of Fashion Week, in banquettes at Butter and even as an escort on the red carpet, Mr. Cheban is often seen with the likes of Scarlett Johansson, the Olsen twins, Kelly Osbourne, the Hilton sisters and Nicole Ritchie.

Mr. Cheban proudly described how he and Paris share a birthday, and when the pair turned 28 and 20, respectively, their party at Eugene was sponsored by Playboy. “I still remember how, on the invite, my name was first and Paris was second. It was ‘WITH Paris Hilton,'” he said, poking the air with his chopsticks for emphasis. Nightlife impresario Noah Tepperberg, who was managing Eugene at the time, counts the event as one of his all-time favorites. “I will always remember that party as one of the best nights of the whole year,” Mr. Tepperberg said. “The guest list was everyone who’s anyone: Lenny Kravitz, Puff Daddy, Carmen Kass, Jay-Z ….”

Who is Jonathan Cheban? He’s not famous, he’s not a celebrity assistant, and he’s not anyone’s lover. Mr. Cheban is one of those Zelig-like creatures, a friend of the famous, who’s somehow managed to break into the most celebrated echelon of our social caste system. While he’s not making any headlines himself, he gets to reap plenty of the benefits of fame.

But who would even know how to go about befriending a celebrity? It’s all about the approach. “He’s not star-struck; he’s not affected,” said Lizzie Grubman, the accident-prone publicist who spent the summer handling publicity for the Hamptons hangout Star Room with Mr. Cheban, has known him for 10 years and counts him among her best friends. “A lot of publicists out there want to be the celebrity, and he’s not like that at all. He’s an entrepreneur.”

Others are not so flattering. “He’s the king of name-dropping-it’s always ‘Jessica told me’ and ‘When Paris and I were down in Miami,'” said one longtime celebrity-party denizen.

Former business partner Jake Spitz believes that Mr. Cheban’s ambition guides him in friendship as well as business. “When Jonathan has his eye on something, he gets it, whether that’s a celebrity friend or a job,” said Mr. Spitz, who reportedly threw Mr. Cheban and others out of their Network PR office and changed the locks during their split back in 2001. “I think Jonathan has an eye for people who can do something for him-which everyone does who’s in P.R. and is successful at it. Maybe he studies developing talent or something …. ”

Mr. Cheban leaned down to check his Sidekick, which was constantly flickering on and off. “It’s the best thing ever made,” he gushed. “I was the first person in the country to get it, even before Lindsay [Lohan] and Nicky [Hilton] and Nicole [Ritchie].”

On his right arm, a white-and-black diamond bracelet spelled out “YOLO.” “It stands for ‘You Only Live Once,'” he explained, then pulled out a Harry Winston necklace featuring his interlocked initials. It sat incongruously on his chest next to the Polo rider on his shirt. “I always need bling to light it up a bit. You know, you don’t want to be just an average person.” An onyx Audemar Piguet watch straddled his other wrist. He used to wear a Rolex that he’d had custom-painted chocolate brown with diamond numerals. “The Rolex got a little boring,” he said, shrugging. “Suddenly every random J.A.P. uptown was walking around wearing one and it was like, ‘Uh, uh!'” When everyone eating at Houston’s is wearing a Rolex, you know you gotta take it up, and the Audemar is definitely the next step up.”

The waiter interrupted, and Mr. Cheban launched into an ordering campaign that put Meg Ryan in When Harry Met Sally to shame. “I’d like the tuna sashimi salad, but with the dressing from the soft-shell crab salad,” he said at one point. “I’ll check that one for you,” the waiter replied. “No, they have it. I get it every night,” he insisted. “Yes, but tonight-” “They’ll do it. They do it for me every time,” Mr. Cheban said firmly.

“My palate is very sensitive with food,” he explained when the waiter left.

He likes being in control. He negotiates the streets of New York in his black 2004 Mercedes CLK because he can’t bear to wait for cabs. And he has a problem with authority figures-something he struggled with during the years before he became his own boss. “It was really hard to take orders. Sometimes I knew I was better than the people I was working for.”

Jersey Boy

These days, Mr. Cheban does have a day job: He’s the driving force behind the celebrity T-shirt line Clarendon and the founder of CommandPR, which has overseen high-profile events like P. Diddy’s white parties, Janet Jackson’s album-release party and J. Lo’s pre-party for the MTV Video Music Awards, and represents top clients like Evian, Polaroid, Radu and even Lean Cuisine. “Everybody else has their work separate, but my life and work are combined. That’s why you’ll never see me falling on the floor drunk,” said Mr. Cheban. “If people see me messed up, then why would they trust me with $10,000 to represent their company?”

Jessica Simpson inadvertently kicked off Mr. Cheban’s T-shirt line when she tugged on one of his tees to get her eyes Lasiked on Newlyweds. “When I saw that episode, I was like, ‘We just had a 20-minute ad!'” said Mr. Cheban. T-shirt sales also soared after Mr. Cheban wisely gave his wares to high-profile friends like Lindsay Lohan and Mischa Barton. The Black Eyed Peas’ Fergie chirped about the line in the September issue of Vogue.

Mr. Cheban’s businesses might now ensure his status on the celebrity social circuit, but he planted those roots a long time ago, when he was, well, just another kid from the ‘burbs. Once upon a time, Mr. Cheban did wait in line at places like Limelight and Club USA. It was the late 80’s, and the Fort Lee High School student was the only child of a real-estate agent (his mother) and a diamond dealer (his father). Even while earning a communications degree from Hofstra, he was coming into the city every night to haunt “It” places like Café Tabac and Casa LaFemme. But he doesn’t say much about it, as if his life’s narrative didn’t truly begin until he’d put down his first and last month’s rent in Manhattan.

“New York clubs and restaurants were just concentrated with models and beautiful people,” said Mr. Cheban, referring to what it was like as a Jersey teen coming into the city. “When you’re 18, you think that they’re living the best lifestyle. Of course, you grow up and realize that models live in miserable model apartments unless they’re high-end supermodels. But then you find other levels of wonderment. You think about other things, like having a private jet, as opposed to being in a nice restaurant.”

After graduating from college in 1995 the 22-year-old finally moved to Manhattan and landed an internship at the public-relations firm Jason Weinberg and Associates. Following that job was an insufferable turn in the research department for The Late Show with David Letterman-“They would make me go on the subway at 10 o’clock at night returning videos!” He spent much of his time sneaking over and trying to assist the talent department.

During his time at Letterman, über-publicist Desiree Gruber of Rogers and Cowan set Mr. Cheban up with an interview at the Los Angeles office, where he got a job as an assistant in the film department. He lasted 10 months in L.A.: “Everyone was in business suits all the time; it was all about agents, cars and swing dancers.” Back in New York, he got a job as an assistant booker at Next Models, where he befriended beauties like Molly Sims and James King and escorted models to film premieres. He grew restless, and soon went to work for P.R. madam Peggy Siegal.

“She was nuts, screaming, but I loved it because she never screamed at me,” he said. “I can still hear her going, ‘Stuff and seal! Stuff and seal!’ when we were at the office until 2 a.m. stuffing invitations.”

One day a call came from Mr. Cheban’s friend, mega-manager Benny Medina (whom he met through Naomi Campbell, whom Mr. Cheban was accompanying to a Vibe TV-show party in L.A.). Mr. Medina wanted Ms. Siegal to handle the $1.5 million birthday bash for 29-year-old burgeoning rapper Sean (Puffy) Combs. Ms. Siegal rebuffed the offer, saying she “doesn’t do that type of event,” until Mr. Cheban begged her to reconsider.

“He dug in and worked 20-hour days for the weeks leading up to it,” says Mr. Medina. “The turnout was so great we could barely handle it.”

After a year of not getting screamed at by Ms. Siegal, Mr. Cheban called socialite publicist Samantha Phipps at Paul Wilmot, and the two of them teamed up with another publicist, Jake Spitz, to form Network PR. Things were humming along when, again, Mr. Medina came calling. This time he hired the trio to organize a birthday party for an unknown actress named Jennifer Lopez at an unopened club called Halo.

“People are extremely loyal to him because if he says he’s going to do something, he does it, and he will never embarrass you by not delivering for your artist,” said Mr. Medina.

During its tenure, Network represented Banana Republic, Baccarat Crystal, Oscar de la Hoya, Backstreet Boys, Playboy, and clubs like Spa and Luan.

“I was like, ‘Oh my God, we’re 25 years old, with a staff of 20, and getting $10,000 retainers!’ Every place we touched turned to gold,” he said wistfully.

The group fractured in 2001 because Mr. Cheban and Mr. Spitz weren’t “on the same page”-a split that played out in the city’s gossip pages. “I didn’t like the way he was fighting with people and screaming at them on the phone,” Mr. Cheban explained, “because we had these big, big clients, and my reputation was so rock solid …. ”

In the end, Mr. Spitz bought out Mr. Cheban’s and Ms. Phipps’ stake in the company, and Ms. Phipps moved to Los Angeles. “It turned out that three cooks in the kitchen didn’t not work. We were way better over the dinner table than we were over the boardroom table.”

Paris is Burning

As Mr. Cheban was tucking into a ball of vanilla ice cream to close out the meal, Nicole Ritchie called. She wanted him to meet up with her and Paris at Marquee, where they were filming the first episode of The Simple Life 3. First he decided to pop into Nobu Next Door and say hi to Mary-Kate Olson (or “M.K.” as he calls her), who was dining with a young man in a baseball cap. “She lives in the area,” Mr. Cheban explained. “This is like her local diner.” After chatting a few moments, he walked back out. ” That’s going to be written up tomorrow,” he sighed. “That was Ali she was eating with, the guy she supposedly dumped David Katzenberg for.” (Indeed, the sighting popped up the next day on the media blog

“New York is tough, because places are so desperate to be written about that they’ll sell out anybody. You have to know where you can go and who you can trust.”

Inside the red-tinted walls of Marquee, wearing a skin-tight, shimmering gold dress, Paris was standing on a banquette, wriggling her butt back and forth for the paparazzi and tossing her professionally extended mane around. Guys wearing shit-eating grins climbed over each other and the furniture to get a look. Next to her, Nicole kept pulling up her too-long strapless gown. A pink diamond ring sparkled on her left hand, which she waved at her boyfriend, D.J. AM-who was spinning records and wearing a silver band on his left hand. ( Hmmm …. ) Mr. Cheban joined them in their private booth, where the girls greeted their friend with squeals and hugs. The Simple producers tried to get the girls to be more animated for the camera. Gamely, they stood up and shook their booties, grabbing Mr. Cheban’s hand and pulling him in for the fun. He did the “sober person’s bop,” bouncing around with them, clapping his hands occasionally. At one point, he lit up a cigarette.

Tommy Lee ducked in and made a beeline for the V.I.P. area, where the group followed in what amounted to a human motorcade of bodies. Paris quickly busied herself with Wimbledon finalist Mark Philippoussis. Bridget Hall’s statuesque frame could be seen across the room. “She needs to grow her hair out,” Mr. Cheban observed. “I’ve known her forever. When she was 17, I took her to that awful Tim Allen movie, The Santa Clause, and was so bored I fell asleep. Very embarrassing.”

“That fucking bitch!” Nicole screamed a bit later, pointing 10 feet away to a strapping blonde wearing jeans and dark, “intellectual” eye glasses. The woman was irate, convinced that the best friends were trying to oust her from her table. “You are not taking my fucking table!” she yelled. Mr. Cheban put his arm protectively around Nicole.

“I want her out of here immediately!” Nicole shouted. The blonde held her arms up in the air in a “bring it on” kind of way. Paris reached into an ice bucket passing by and, cackling, launched some cubes at her. “You’re the fucking ugliest bitch ever!” Paris screamed. Mr. Cheban doesn’t mind when he has to play bouncer for his chums. “I protect my friends when I’m out with them, whether we’re at fashion shows, clubs or just walking outside. I’ll block photographers’ shots and I’ll piss the paparazzi off,” he said. “I was in Mr. Chow’s with Mischa Barton having dinner, and a photographer came in the restaurant and just went and started taking pictures of us eating. And I literally went up to him and threw him out of the restaurant. I thought that was so disgusting.”

Those moments serve as reality checks for Mr. Cheban. “When we’re all out at Butter or something, no one’s thinking about who’s famous. It’s only when you go outside and suddenly they’re getting their photograph taken that you remember. Otherwise, it’s like hanging out with your friends from college. We have our own inside jokes and our own lines …. ”

Of course, that’s also a part of the job. “No celebrity is anyone’s friend,” said one longtime publicist, who scoffed at Mr. Cheban’s stable of celebrity show ponies. “They just hang out with people who can do something for them, and Jonathan makes them feel special and important. It takes a certain kind of personality to put up with that stuff, because it’s a 24-hour job. It’s exhausting.”

Later, on the way in to the members-only club Upstairs at Cipriani the doorman eyed Mr. Cheban’s Louis Vuitton shoes appreciatively. “Some day I’ll get there,” the man sighed longingly. “I’m not quite there yet, but some day.”

“Don’t worry-it took me awhile to get them, too!” Mr. Cheban said. “Actually, it totally didn’t,” he confessed minutes later. “I just didn’t want to make him feel bad.”

At around 2:30, Mr. Cheban called it a night, the streets nearly vacant as his Mercedes purred along. When he got home, Mr. Cheban was going to TiVo a reality show ( Cold Turkey, about people trying to quit smoking)-something he does every night until at least 3 in the morning.

At a stop light, he confessed that he finds going out to be a “pain in the butt.” “When you deal with a lot of people and a lot of people know you, it becomes a little bit of a hassle. You walk in and end up saying hi to 50 people who want to talk about nonsense. That’s why I like to go out with celebrities who get a lot more attention than me. I kind of hide behind them a little bit. It’s a good decoy.”

The Art of the Schmooze