(FORTUNE Magazine) – Edgar Bronfman Jr. threw a party in June commemorating the 40th anniversary of the Four Seasons restaurant. Donald Trump was invited. Barry Diller too. It made all the gossip columns; Liz Smith burbled that it was "the invite everyone wants." It was, in short, precisely the sort of scene--a restaurant stuffed with celebrities stuffing themselves--that Kurt Andersen and Graydon Carter would have cut to ribbons during their heyday at Spy, the satirical magazine that served as the slambook for Manhattan during the late 1980s. For a few years Andersen and Carter fashioned a role for themselves as the smart-ass kids standing outside the velvet ropes, blithely tossing acid at those on the other side.

But the celebrities in attendance at the Four Seasons didn't have to worry about that: Safely inside, co-hosting the event, was a tame Graydon Carter, now the editor of Vanity Fair, the most celebrity-friendly magazine this side of InStyle. Andersen, meanwhile, was on the other coast, doing the umpteenth interview to attempt to turn Turn of the Century, his lavishly reviewed, name-dropping doorstop of a first novel, into a bestseller. (The middling sales of the book even prompted a hand-wringing item in the New York Times, which claimed that "Seemingly, the book has it all"--and proceeded to list its come-hither charms as follows: "the media universe, cyberspace, Wall Street, Manhattan, Hollywood, Silicon Valley, society being confounded by the very communication devices that are supposed to make people's lives easier." Can't imagine why folks are avoiding it.)

Back in Spy's heyday, few would have predicted that this was where its editors would end up. Who could have guessed, back when they were mocking the Jay McInerneys and Tina Browns of the world, that what Andersen and Carter wanted more than anything on earth was to actually be Jay McInerney and Tina Brown?

The Spysters' stock-in-trade was clued-in irony, and they are not unaware that this looks a bit weird. "Thank God Spy magazine isn't around now," Carter cracks. Or as Andersen puts it, "I don't think that there's any shortage of appropriate targets for Spy. Probably I would be one of them now, and that would be okay too."

But for all their hale-good-sportsmanship, there remains something deeply disingenuous in Carter and Andersen's ascent. Spy was nasty, sure, but the nastiness was wrapped in a moralistic tone, one that seemed to be genuinely outraged at greed, hypocrisy, and the tendency to elevate celebrity above substance. "It's okay to mock Donald Trump's personal grooming," the subtext went, "because Trump himself represents something truly distasteful." Indeed, Andersen now says one of the two stories he regrets running was an embarrassing item about the foibles of a low-level Times editor, because he was "a little guy and didn't deserve the ding he got"--implying that the question of "deserving it" played a major role in the magazine's decision-making.

(The other story he regrets, by the way, had a very different problem. "It was not so much about the piece," he explains, "as it was the fact that the piece was about the relative of a good friend of mine, and it sort of ruptured that relationship for a long time." Readers of Spy may recall that displays of favoritism were rich fodder for the magazine.)

The Spy guys' outrage at a culture of celebrity seems to have dissolved as soon as each walked out the door. Carter now edits a magazine that thinks the following is a perfectly acceptable way to begin a story: "The only thing you can really, truly hate about Will Smith is that he is not your best friend and never will be." And for all Andersen prides himself on having a wry, ironic take on the media elite, his book has benefited from his position at the center of that elite. Turn of the Century arrived upon a plume of hype, feted at celebrity-studded parties hosted and attended by editors whose publications soon published gushy reviews--reviews that almost invariably contained a disclaimer along the lines of "I'm a friend/colleague/former employee of Andersen's but..." ("I was amazed and happy with overwhelming reviews," Andersen modestly told the Times.)

Carter, for one, is at a loss to explain just how this transformation came to pass. "It's not the evolution I would have thought would happen," Carter says. "I'm very antiestablishment." The editor of a magazine that puts out an annual Establishment Issue, antiestablishment? "That's 'The New Establishment' issue, that's different" Carter replies, then happily concedes, "There are all sorts of conflicts in what I'm saying. I understand that." Is he the new Tina Brown? "Not at all!" he exclaims. "What does that mean, first of all, before I say 'not at all'? I mean, I'm sure it'll be the same answer, but what do you mean?" (Told that it meant cozying up to celebrities, Carter stood by his statement.)

Almost as puzzling as Carter and Andersen's metamorphosis is the warm embrace they've received from those they mocked. Both now work for S.I. Newhouse Jr., whom they routinely caricatured as a Howard Hughes-esque dilettante. And Andersen's book party and Carter's Four Seasons shindig featured people who had come in for rough treatment in the pages of Spy. (See table opposite.) Andersen says he counts two former targets, Miramax chief Harvey Weinstein and restaurateur Brian McNally, among his friends; Carter now says of the man he famously dubbed a "short-fingered vulgarian," "I happen to like Donald Trump." (Trump returns the compliment: "I think Graydon has done an incredible job at Vanity Fair," he says, although he takes exception to Spy's characterization. "I'm 6-foot-3," he notes, "and have rather long fingers.")

Andersen, attempting to explain why Weinstein and McNally would want to be friends with a man whose magazine called them a sleaze and a deadbeat (respectively), comes up with the following theory: "In a certain funny way, those sorts of friendships begin from a cleaner base or something, because there's no--I don't know, there's just something kind of--there's a bond. If you can get past having someone shat on you, or being responsible for somebody else having shat on you, I have found in a couple of cases, there's actually, it's an oddly kind of a full--I don't know about deeper--but a more adhering kind of friendship can develop out of that. Anyway, that's my experience." Has anyone else had this experience? Anyone? Andersen adds, "There are certain people who can get kicked in the shins and understand that that's part of the game," unconsciously echoing Carter, who offered this explanation: "It was just part of the game."

And that may just be the most pathetic statement about Spy: It was never anything more than a game. Nobody would ever have mistaken Kurt or Graydon for H.L. Mencken, but it was assumed that their magazine had some sort of underpinning beyond their own ambition. Kurt and Graydon claimed to be shocked (shocked!) at the excesses of the '80s, but their shock was just a way of getting the attention of the powerful and sharing in those excesses. And those who were mocked can forgive Andersen and Carter just about anything, as long as they get favorable coverage and an invite to the next party. At the time, Spy may have looked like a manifesto; turns out, it was just a calling card.

Confidential to Kurt Andersen: Hey, Kurt? Do we have a bond now? Wanna go bowling sometime?

--Tim Carvell