By Frank DiGiacomo

December 26, 1999 | 7:00 p.m

Three weeks before the end of 1999, recording artist and actress Courtney Love walked into a lightstorm of flashbulbs at the Ziegfeld Theater on West 54th Street and Sixth Avenue. Ms. Love was attending the premiere of Man on the Moon , a film depicting the life of Andy Kaufman, a comedian whose work was so original and disconcerting that it made people angry.

Ms. Love had to be able to identify with that. Her life and her art–the marriage, the drugs, the mouth, the music–had once polarized people. Watching Ms. Love, her hair tousled and dirty, her lipstick smeared, jump into the mosh pit of overheated boys at a Hole concert and almost get ripped apart was terrifying and exciting and sexual and always fascinating. But any vestiges of that past self seemed erased as Ms. Love stood for her photo op at the Ziegfeld. The pictures that resulted show a sleek Ms. Love pulling back the hip-high slit of her gauzy dress to reveal a magnificently toned leg that ended in a white strappy Roman sandal. Her professionally coifed hair, done up in kind of a pageboy, was fashionably straight, and the smoldering look she threw the paparazzi combined sex and parody. She was Courtney Love, all right–but not your mother's Courtney Love. As for the nice-looking man holding Ms. Love's hand, there was nothing wrong with him–and that was the whole problem: The woman who had married the dark, brilliant Kurt Cobain was now holding hands with a Geffen Records executive named Jim Barber who looked like a young Joel Grey, as he stared self-consciously into the cameras. New York has always been a celebrity fishbowl, but in the five years that we've been doing the New York Observer 500–a one-year ranking of the number of citations received by celebrities in an intensive dredging of the New York media–its architecture has changed to resemble one. The network morning shows all broadcast from glassed-in studios, and MTV has erected a Times Square terrarium that allows the Backstreet Boys to preen two stories above the crossroads of the world while teenage girls risk their lives to cram onto tiny triangular traffic islands and hyperventilate. Throw in the paparazzi, the camera crews from Entertainment Tonight , Extra , CNN, MSNBC and the Fox News Channel, their complementary Web sites and other Web sites, the do-it-yourselfers trawling parties with foreign press credentials and digital cameras and there is very little that goes on in New York that involves someone famous that isn't devoured immediately; there are cameras almost everywhere. And cameras lead to consumption. It's reminiscent of the scene in Roadrunner cartoons where Wile. E. Coyote lights off the rocket, which goes straight up, then straight down: The New York media collect these images and stories and sends them out on feeds and wires, and they go out and come right back into our homes via our televisions and computers, often within seconds of being transmitted. New York has become a massive, wired soundstage, a big live studio for a new kind of hybrid, the calculatedly cross-bred celebrity. For a decade now, we've been bombing ourselves regularly with this celebrity ordnance, and the process has left us shellshocked, but clearly not sated. Working as a columnist this past year has often felt like walking through a premillennial Invasion of the Body Snatchers (the Don Siegel version). The parties still happen. The celebrities still come. On the surface everything looks fine. Like Ms. Love, everyone has been coifed, styled and dressed. Even Madonna is speaking with a British accent these days. Yet, something feels undeniably amiss. Part of it has to do with this gentrification or mass beautification of celebrity taking place courtesy of the designers, stylists, publicists and fashion magazines who have proliferated over the years. The celebrities certainly look great, but similar. This year, it was straight hair and bare midriffs for the women; that monochromatic shirt-and-tie look for the guys. Everyone has a special cause these days, and it seems like everyone thanks God when they win an award. The gaping maw of 24-hour media that is so hungry for celebrity content has become a barrage of coverage so relentless, so round-the-clock, that it is growing more difficult to differentiate one celebrity from another. Not only do they look alike, they are now being thrust upon us with the same mind-dulling intensity. Celebrities used to be identifiable by their niches. Designer Calvin Klein and Bianca Jagger represented the push-the-envelope euphoria of New York's Studio 54 crowd. Robert De Niro and Harvey Keitel were the no-nonsense New York boys who lived in TriBeCa before TriBeCa was cool. Julia Roberts exuded a playful sexuality that seemed at home on either coast. Warren Beatty and Jack Nicholson were the smart satyrs of Hollywood royalty. Christy Turlington and Naomi Campbell were members, along with Linda Evangelista, of the trinity of supermodels. But those delineations are crumbling in the digital era. The technological revolution has meant that the world, not just America, is now a melting pot. The idiosyncrasies of various cultures are being paved over by our dominant Hollywood-and-Hip-Hop-driven culture. Just as the avenues of this city have become a repeating pattern of Gap stores, Starbucks locations and Radio Shacks, celebrity has become familiar but unexciting, a tapioca of nonthreatening traits tailored for the lowest common denominator. The wired world has made it possible for anybody to appear anywhere instantly via modem. And with that kind of potential exposure, it pays to look and talk in a way that appeals to the largest possible audience. Ricky Martin, Jennifer Lopez and Salma Hayek may represent a Latin invasion of artists, but the work that has made them famous is pretty standard American popular fare. That lack of differentiation is certainly present in the climax of this year's New York Observer 500. When we started this project in 1995, the idea was that the city's gossip columnists were kingmakers. Because they were on the leading edge of celebrity news, they determined who was important and who was not; who should be celebrated and who should be scorned. Because this information filtered through them first, they determined the hierarchy of power in New York; a late-20th-century equivalent to Caroline Astor's ballroom. But four years is an eternity when there's a technological revolution happening outside. And that revolution has made it practically impossible for New York's newspaper gossips to continue to determine that hierarchy given that news organizations and news outlets from around the world are only a mouse click away. And they have all gotten into the gossip game. As a result, the agenda that once was set by the New York columnists is up for grabs. Last year, it was set by Matt Drudge, a guy with a fedora sitting in an apartment in California. This year, Mr. Drudge, who has parted ways with Rupert Murdoch's Fox News Channel and the weekly forum it had given him, already seems to be a distant memory. Indeed, this Observer 500 ranking seems to reflect the grayness of a limbo-like period that existed post-Lewinskygate and pre-millennium. A year in which the most significant event was a loss–the death of John F. Kennedy Jr.–that seemed to leave New Yorkers feeling even more disconnected. Perhaps it is appropriate, then, that Bill and Hillary Clinton and Monica Lewinsky, rank, respectively, one, two and three in this year's Observer 500. They were key players in ushering in an era where gossip, government and journalism became so inextricably intertwined that even that vaunted pillar of the Fourth Estate, The New York Times , had to get its spotless hands dirty. And they are, all three–at bloody cost–hard-bitten professionals, stage managers of their own performances, and growling protectors of their privacy. But how many times can a person watch Ms. Lopez galumphing around a stage in a short dress and a headset? How many stroller shots of Woody and Soon-Yi? How many Baldwins, how many Penns, Lewinskys, Paltrows, Gumbels, Trumps, all increasingly more rife and less glamorous than ever before. And yet, put together, their interconnectedness adds up. If there is one person on this year's list who's got the New York Observer 500 list wired, it is Miramax Films co-chairman Harvey Weinstein. Mr. Weinstein appears on the list at 26, up from 35th place last year. He is not your typical celebrity. Gucci does not make anything in his size. But look at the ties Mr. Weinstein has on this list: He is a major supporter of President and Mrs. Clinton (1, 2); Miramax's team of publicists has helped put Gwyneth Paltrow (11), Ben Affleck (23), Matt Damon (46) and Judi Dench (104) on this list. Mr. Weinstein is in business with Talk editor in chief Tina Brown (40); he employs Jerry Seinfeld's (62) publicist; he was trying to turn the Brooklyn Navy Yards into a film studio with Mr. De Niro (18), and he's slated to do the film Gangs of New York with Leonardo DiCaprio (20) and Martin Scorsese (84). And that's just in the top 100 or so. And then, at the other end, tied for last place with Yasir Arafat and Public Advocate Mark Green is Jocelyne Wildenstein, a woman who represents a Brazil -like vision of the 21st century. In between, however, is a hobo's soup of names that seem to have little in common besides fame or, in the case of one dictator's case, notoriety. Check out this progression: 53: Marilyn Monroe; 54: Harrison Ford, Jennifer Lopez and Newt Gingrich (a tie); 57: Senator Daniel Patrick Moynihan, Mariah Carey and Martha Stewart (another tie);60:Barry Diller and Prince Charles(yet another tie); and 62: Frank Sinatra, Attorney General Janet Reno, Mr. Seinfeld and Pamela Anderson (tie again). Little in common, perhaps, but it sure reads like a guest-and-story lineup for some cable news network's prime-time day part. There are two dead legends, Monroe and Sinatra; a funny guy, Mr. Seinfeld; one leading man, Mr. Ford; one newly minted star, Ms. Lopez; one jiggle queen, Ms. Anderson; a royal, Prince Charles; a member of the Clinton Administration, Ms. Reno; a self-made woman who has just gone public, Ms. Stewart; a pop singer, Ms. Carey; and two public officials, one retired Republican, Mr. Gingrich, and one about-to-retire Democrat, Mr. Moynihan. And of, course, one media mogul, Mr. Diller. While their reasons for being famous are all entirely different, in this 24-7 digital they are there because they all fill space. On MSNBC, CNN and America Online's Influence page, you are either a one or a zero. Famous or not famous. Of course this list still functions as a sort of S.&P. 500 of celebrity. For instance, Mr. DiCaprio's down 13 points from last year. Not a very precipitous drop given that Mr. DiCaprio has been laying relatively low and doesn't have a movie out until next year. Mr. DiCaprio's manager, Michael Ovitz, has also returned to the list after an absence. He's at 153. The 2000 Presidential race has landed a number of candidates on the list for the first time. George W. Bush, who with those rumors about his alleged drug use and that Quayle-like foreign pop-quiz debacle appears to be the most readily gossip-friendly of the bunch, makes the highest debut of anyone on this year's Observer 500. Mr. Bush clocks in at No. 7. Sixteen rungs beneath him is another newcomer, Bill Bradley, followed by Senator John McCain at 40; Gov. Jesse Ventura of Minnesota at 84; Dan Quayle at 98, who nonetheless has already dropped out of the race; and Gary Bauer at 345. None of these men were on the list last year. A big public romance certainly has levitative properties. Newcomer Jessica Sklar, who is Mr. Seinfeld's intended, is tied for 258 with Joan Collins (hopefully not a portent of the future for Mr. Seinfeld), and another P.R. executive, Howard Rubenstein. Actress Ellen Barkin tied for 104th place with mouthy media mogul Ted Turner. (We're probably going to get hurt for noting this, but do we sense a trend?) Ms. Barkin's been getting some press recently for some Sapphic love scene she shares with Peta Wilson in an upcoming movie, but, clearly, what pulled her high up on this year's list is her continuing love affair with a very rich heterosexual, billionaire Ronald Perelman. Indeed, the whole Perelman mishpocheh is in ascent following last year's seemingly interminable court battle over support issues following Mr. Perelman's divorce from Democratic Party activist Patricia Duff. Ms. Duff crested at 84, up from last year's 395 berth. Even Mr. Perelman's ex-wife Claudia Cohen, who got entangled in the court proceedings when Ms. Duff wanted to look at her settlement, is up a good 65 points to 220 this year. Entrapment co-star Catherine Zeta-Jones came out of nowhere to land at No. 66 this year, no doubt, because she, as another section of this paper put it, is actor Michael Douglas' latest … well, never mind. Inexplicably, Mr. Douglas' star fell four notches to 29 this year. Perhaps he should star in a same-sex love scene with some up-and-coming actor or horn in on Ms. Barkin's action. Mr. Douglas and Mr. Perelman are good friends, after all. Crime may be down, but Police Commissioner Howard Safir is up, way up to 232 from last year's 429. Mr. Safir is tied with Cuban President Fidel Castro. The most precipitous drops belong to actor-director Edward Burns, who fell from 76 last year to 495 this year. This seems damned unfair, given that Mr. Burns has been dating The Spy Who Shagged Me 's Heather Graham and, from all reports, is making the most of it. The other two big droppers are both sitcom stars who no longer have their sitcoms: Mad About You 's Helen Hunt, an Oscar winner in 1998 and an ex-sitcom star in 1999, who fell to 409 from 86; and Ellen Degeneres, who dropped from last year's berth of 50 to this year's 416. And Celine Dion's decision to take a break from her music career and spend time with her husband may have been a fortuitous one. The Titanic love theme singer sank from last year's buoyant 96 to sleep with the fishes at 416, tied with Ms. Degeneres–and someday perhaps to be shared by Ms. Lewinsky and Mr. Starr–though probably not the Clintons. The flashiest gift that democracy can give is, of course, celebrity. But the prize most fervently sought by those who have been there and have drawn some wisdom from the frenzied ordeal of exposure is, finally, the culture's hardest-won right–the restoration of privacy.