A combination of earlier magazine work and new blog posts

P. Diddy Plus 30: The Evolution Of The Celebrity Entourage

P. Diddy Plus 30: The Evolution of the Celebrity Entourage

We couldn’t decide what to do on a recent Sunday evening in South Beach. Too pale for a good entrance at La Piaggia, and too lazy to drive to Fort Lauderdale to see the Princess Di exhibit, we settled on a classic South Florida cultural event, The Source Hip-Hop Awards. That the awards had been held in Miami since 2001 made them “classic” by local standards.

We listen to hip-hop, but our interest in The Source awards was not who won what. We wanted a personal and up-close view of the outrageous preshow parade of microskirts, oversized basketball jerseys accented in 24-karat-gold threads, custom-made Manolo Blahniks, and enough Cavalli and Tommy couture to bring smiles to their companies’ accountants. And don’t forget the bling. Somebody is forcing diamond miners to do serious overtime. Belts, earrings, necklaces, car ornaments, rings, cell phones-is there something onto which you can’t stick a diamond?

There were all the appropriate cars. A Rolls Phantom, still looking hearse-like. A few Bentleys (we personally believe they are an awards curse, as we have never seen a winner arrive in one at the Grammys, Emmys or Oscars). Ubiquitous Escalades and Hummers, mostly tricked out with sound systems that could deprive prisoners at Guantanamo Bay of sleep. But the evening’s highlight was a bright-yellow Lamborghini rumbling up the drive. Cool, we agreed. The driver had the requisite music look (quasi-dreadlocks, oversized jersey, earring the size of a baseball). He drove about halfway up the drive before popping the clutch and sliding back to the start. This went on for an excruciating 10 minutes, with the driver panicking about his inability to drive a stick shift on a quarter-million-dollar car. Arriving guests and fans taunted him.

“Somebody oughta help that boy!” shouted Wycliff Jean, emerging from his own limo. Finally, a cop approached the driver, who sheepishly said he was with the Winans crew.” Winans’ friend let the cop coach him on how to use the clutch. In a few minutes, he was grinding the hell out of the Lamborghini, but it finally lurched away.

At least for that night, it certainly beat looking reverentially at Princess Di’s old shmattes. We later stopped for a drink at one of our favorite Beach bars and told the bartender what we had seen.

It’s not surprising,” he said. ‘The posses that hang around the stars are so amateurish they have totally ruined the idea of an exclusive group of friends who are out for a night with the celebrity. The day of the velvet rope is dying.”

The velvet rope is dying? We live in South Beach, where it almost seems as if no self-respecting restaurant, bar or club could open its doors without one. It is as prevalent as the fire extinguishers required by City code. And the rope was actually mandated by the code of hip, an even less flexible standard.

But the bartender had unwittingly sparked a conversation that we thought was a good story to follow. Trisha had been a regular at Studio 54 in its prime, when it was packed with everyone from Christopher Street leather queens to the cream of New York’s straight club life (okay, South Beach gossipers, don’t even try to guess at Trisha’s age-it was very easy to get into Studio considerably underage, especially if the doorman controlling the velvet rope was your neighbor, as was the case with her. And remember, underage wasn’t really a problem at Studio. Lots of people were openly doing drugs, there was public sex in the balcony and the VIP basement, and enough amyl nitrite was being snorted on the dance floor to revive Dick Cheney in case of another heart attack).

But at least Trisha had the Studio experience, where partners Steve Rubell and Ian Schrager (Ian now of the Delano, Shore Club and other local hotspots) literally invented the velvet rope. What had they let loose on the world? And is this its death knell in South Beach as we go into the 2005 season?

One thing is certain: The entourage you’re likely to find attached to a celebrity today is not your father’s posse. It has changed dramatically from the time Frank Sinatra formed it in the 1950s. Before he hit it big, an assortment of rough-edged friends from his early days in Hoboken, New Jersey, went everywhere with him. But once he achieved stardom, Frank’s entourage was other stars. In 1955, in Vegas, after five days of heavy partying with pals Humphrey Bogart, Lauren Bacall, Judy Garland and David Niven, Bacall looked at the ragged group and dubbed it the “Rat Pack.” It stuck. After Bogart died, Sinatra brought in Dean Martin, Joey Bishop, Sammy Davis, Jr., and the only woman allowed in, Shirley MacLaine.

“Back in the day of the Rat Pack it was more regal and sophisticated,” Sean Saladino, owner of SoBe’s Rok Bar, told us. “But times have changed and clubs have become more commercialized. It’s not as classy as the days of the Rat Pack, and never will be again.”

Over the years, Hollywood stars tried copying the Rat Pack magic. But in the 1960s and 1970s, the entourage seemed passé, as though the Age of Aquarius made it cooler to be on the scene with just a couple of friends instead of a crowd of 20. All that changed with Studio 54. Studio’s velvet rope meant something, and was more than the fancy door decoration that it appears to be at many local clubs. South Beach doormen sometimes waive cover charges and pass out drink tickets to entice customers on slow nights. At Studio, doormen like Mark Benecke – who ran The Shore Club’s SkyBar for a year – prided themselves on turning away whomever they wanted, celebrities included. No bribe could buy your way in.

So the only way to enter for many was to be part of an entourage of a regular. Calvin Klein, Halston, Bianca Jagger, Liza Minnelli and Andy Warhol had slavishly loyal groups hanging around, and each was unique. Warhol surrounded himself with models, low-level celebrities and some holdouts from his 19605 Factory days. Calvin and Halston were rivals for the prettiest gay boys, each looking more buff than the other. Taking control of a corner of the club, the Studio elite held court encircled by their entourages, and the wannabes tried in vain to break in.

“At Studio, it was all about just getting into the club,” says Rok Bar’s Saladino. ‘They made it so exclusive to get in, that was all people were worried about.”

“Here in South Beach, everyone pretty much got in during the early days,” recalls Tara Solomon, who has been involved with the night scene for more than 15 years and now runs her own successful PR company, Tara, Ink. ‘We all went to the same clubs-Velvet, Club Nu, Joseph’s, Sempers and Warsaw.”

“But South Beach did develop a pick-and-choose velvet-rope policy for a while,” says Gerry Kelly, the Irish-born club impresario who ran a half-dozen venues before his current venture, State. “When I came in ’92 and had Bash, we had a strict velvet rope, and the first two years of Level from ’99 to 2001 we had ‘pick and choose.’ But today in South Beach there is too much supply and not enough demand. Being a nightclub owner is the closest thing to being a rock star, so a lot of investors with extra cash have opened places here. And it’s not just clubs: On a typical weekend night, you have 60 parties to choose from, from a champagne reception for Gucci in Bal Harbour to Ted Baker’s party at Merrick Park to the pool bar at The Shore Club to Mansion to State to whatever. That is why the velvet rope is gone here, really.”

“That is actually a good thing,” says Kurt VanNostrand, the owner of downtown Miami’s hip Pawn Shop. ‘The strict velvet rope involved a lot of attitude and rudeness and you can’t do that forever and not turn customers away. We can fit 600 people into Pawn Shop, and we have a rope, and don’t take the first 600 who arrive each night. But we’re very easygoing. No one is going to be humiliated here.” So if the velvet rope is largely for decoration and no longer the rigid barrier it was during Studio days, what gives a celebrity clubber extra cachet?

“Today, since it’s not about getting in, it’s about how you make the entrance,” says Saladino. “For a lot of young stars, it is all about how important you are, and the size of your entourage is key to that.”

The posse is back in fashion. Some stars think the larger the entourage, the bigger their fame. A few years back, no one in Hollywood was better at mixing it together than Leonardo DiCaprio. He had a frat house of young men, some of whom were famous, like himself, and others like Tobey Maguire, who were just about to break out In Hollywood it was dubbed “the Pussy Posse” for its relentless pursuit of anything in a skirt. And when Leo rented a house in Miami last year, his entourage carried his cash and took care of all expenses, even at clubs and restaurants. But DiCaprio has evidently outgrown his posse.

“Leo will come in with Gisele [Bundchen, his Brazilian supermodel girlfriend] after eating at Nobu,” says Saladino, “and be completely unnoticed. When he was younger he needed a group to show he had made it, but no longer.”

Not everyone outgrows the need to travel with a posse. Gray hair doesn’t stop George Clooney from sometimes moving around with a small army. On being told that Mark Wahlberg -who, like Clooney, has his own large gang-said his posse could kick Clooney’s posse’s collective ass, Clooney said, “That’s true. They could kick our asses. We’re all old men. But we have money. We can buy people who’ll kick his posse’s ass.”

But when it comes to posses, the Hollywood stars have really been left in the dust. The real kings and queens today are rappers and hip-hop stars. Your bling, wheels and clothes might measure you, but your status in the urban world is also marked by the size of your entourage. The beefy security guys in black Prada suits packing Glock 9mm pistols don’t even count. We’re talking groups composed of wannabe rappers, girls who are barely dressed and constantly flashing their new implants, and “friends” from the ‘hood they haven’t seen in 20 years.

“The major difference between celebrities today and 10 years ago,” says State’s Kelly, “is they run in bigger posses. It is a statement from the hip-hop community. They show their wealth by the diamonds, penthouses and cars. Instead of renting a penthouse in a hotel, they will take an entire floor. And instead of arriving in a limo at a club, they arrive in 10 Hummers.”

The Pawn Shop’s VanNostrand has seen urban stars arrive with more than 50 people in tow, in a procession of Escalades. Sometimes the group includes young rappers, people who are hoping that one day they might be famous enough to command their own posse. When 50 Cent was riding the wave of his explosive debut last year, Get Rich or Die Tryin, he was never seen without his G-Unit, which included Lloyd Banks, Young Buck and Tony Yayo. But they weren’t there just to be part of the typical rapper’s entourage; they were in training for their own turns in the spotlight. And hanging out with 50 Cent helped work magic on their careers.

But not everyone can be so lucky as to attach themselves to Paris Hilton’s “babe” squad or get the invite to join the limo with Britney Spears or P. Diddy. And club owners have trouble figuring out where an entourage ends. Sometimes a star such as P. Diddy will hit the front door and his assistant will yell, “P. Diddy and 30.”

“It’s hard to figure out who is with them or not,” says VanNostrand. “Once I had to tell an artist he had too many, and he narrowed it down to 10 and left another 30 outside.”

The future for controlling entourages and the velvet rope might be seen in the hottest club in Barcelona. The Baja Beach Club is using an 8 implantable microchip to identify their VIP members and friends. A small chip the size of a grain of rice is inserted surgically in part of your body, right under the skin. It means you get immediate access to the club and pay for food and drinks without any cash, credit cards or ID. And if you get too stoned or drunk to remember where you are, at least the club can scan your ass and tell you which star you should be hanging out with. Technology saves the entourage.