Hey! Remember Us?

Paging through this slightly premature-feeling but “oh heck, why not” retrospective of the late, great Spy magazine, which bungee-jumped onto the scene in 1986 and limped sadly away over a decade later, is bound to be a discomfiting experience for any writer or editor working in New York City. And writers or editors working in New York City are probably the only people who will be able to muster the stamina for the book’s dense, fine-printed entirety. It’s kind of like a very long alumni newsletter.

Unlike Saturday Night Live’s similar-feeling oral history, Live From New York, which was assembled by professional outsiders, Spy: The Funny Years is an inside job, a somewhat self-congratulatory if thoroughly enjoyable vanity project assembled by a former Spy sub-editor, George Kalogerakis, under the supervision of founding über-editors (as they would’ve put it) Kurt Andersen and Graydon Carter, refugees from Squaresville, white-shoed, WASP-y Time and Life.

The book’s subtitle suggests the famous Fellini-inflected line about “the early, funny ones” in Woody Allen’s Stardust Memories, but Mr. Andersen and Mr. Carter’s brand of humor was not in the gentle Jewish tradition of Mr. Allen; it was a goyish, detached, slightly cruel humor. These men presenting themselves as the consummate insiders were in fact from the sticks themselves (Nebraska and Canada, respectively, though Mr. Andersen did get polished up like a Red Delicious apple at Harvard, where he was on The Lampoon). They had a great Sinclair Lewis–like scorn for the ignorant, unintellectual power structures that run our lives.

But their vision of New York, under the cellophane layer of cynicism, was incurably romantic and a bit collegiate: the city as sort of a large, glittery snow globe swirling with artists and socialites and actors and millionaires (and here were two punks come to smash it up); a place where men and women got dressed up in black tie and cocktail dresses, went out, got drunk and groped furiously in the cab on the way home; and, most significantly in an encroaching video age, a place where words still mattered.

There are lots of amusing photos of Kurt and Graydon as Angry Young Men here, staring fiercely into the camera, but the most striking one is on page 154: two guys fat and thin, nostrils slightly aflare as if to be more receptive to all those hot late-1980’s cultural currents (sundried tomatoes … Hammacher Schlemmer … Donald Trump), posing in dotty ties and striped shirts in the shiny-floored, white-pillared Puck Building, where Spy was produced and the archetypal late-80’s movie When Harry Met Sally, with its gentle, proto-Seinfeld-ian assimilated-Jewish humor, was filmed. If there were a Spy movie, Mr. Andersen and Mr. Carter might’ve been played by Andrew McCarthy and Judd Nelson (“insufferable punk actor,” to quote from the magazine’s much-copied “Separated at Birth?” series). Together with publisher Tom Phillips, they formed a glorious triad, swiftly headed the way of the Supremes. And everyone wanted to work for them.

Appended with a long roster of contributors—a few renowned, most obscure, all apparently obscenely underpaid—this is a tribute so media-incestuous as to give the reader a migraine, an effect enhanced by the shrunken-mimeograph, cut-and-paste quality of its visual material.

But never mind the production values. To read Spy: The Funny Years as a New York City magazine writer or editor is to flush with shame realizing how many of your clever little story ideas—like the one about how many powerful people happen to be short (“we’ll call it The Royal Wee!”); or the proposed year-end special of a taxonomy of New York City’s elite laid out as if in a high-school yearbook; or the first-person account of wearing a padded Miracle Bra around town to see if anyone treated you differently—were already done, more thoroughly, more authoritatively, more snappily, by Spy. See “Little Men,” 1987, with its list of Condé Nast Runts, p. 44; 1991’s “Spy High,” p. 249; and “Busty Like Me,” also from 1987, p. 79.

And yet, you didn’t even read Spy in its heyday! (To linger in the second-person tense of late-1980’s Brat Pack novelists, so roundly mocked by the magazine.) You grew up in New York City, but weren’t nearly cool or “savvy” enough for Spy. Your parents subscribed to The New York Times and The New Yorker and The New York Review of Books and—yes—The New York Observer, all stacked up in tidy little rows on the dark-wood living-room coffee table in front of an aging leather sofa (pre–Yuppie Porn, p. 100). Not Spy, which managed to be both refined and rude. But the magazine was so smart, so influential, so zesty and zeitgeisty, you must have absorbed its ideas by osmosis. It was the one toted around by your sardonic, slightly older friend, the one the boys unjustly considered “fast” (this was the conservative Reagan-Bush late-80’s, pre-“fuckbuddies”), the one who took you to the now-defunct nightclub M.K. on lower Fifth Avenue one night when you were 16, where you sat in a plush armchair, applied a fresh coat of L’Oréal Rose Potpourri lipstick and wondered what exactly all the fuss was about. Maybe the raffish Atlantic Monthly Press publisher Morgan Entrekin was there that night—a frequent gleeful target of the Spy reporters, who trailed the city’s most energetic nightcrawlers in a cherry-red Ford Tempo (“A Hard Day’s Night: A Documentary Account of the 1988 Celebrity Pro-Am Ironman Nightlife Decathlon Championship,” p. 132)—but you wouldn’t have recognized him or known why he mattered.

But can we just pause and mark that forever-lost moment in history when Mr. Entrekin, a publisher of books, was considered a local “celebrity”? One can’t exactly imagine such a character popping up these days in Gawker Stalker, a case study of how the dear, grimy enclaves of Spy’s New York have been invaded and scrubbed clean by Hollywood celebrities waving fistfuls of cash.

Had it not been for Spy, of course, there never would’ve been a Gawker Stalker (Spy loved maps, anonymity), nor Ashton Kutcher’s Punk’d (Spy loved pranks), nor VH1’s “Best Week Ever” (Spy loved postmortems). Nor, the creators suggest a bit grandiosely, a Daily Show (though in fairness, the Brits—and even Saturday Night Live—have been satirizing TV news for decades). They dared to penetrate The Times, which until then had been the Vatican. They took the stuffing out of critics, with “Review of the Reviewers” and “Logrolling in Our Time.”

Then there are the considerable typographical legacies: The lists, the graphs, the o-matics, the clip ’n’ saves, the “charticles.” Spy might not have been solely responsible for the Age of Irony (though it certainly was its most sophisticated chronicler), but we can blame it for the long march of those little neckless, floating heads across the pages of mainstream publications from Entertainment Weekly to The New York Times. Talk about dubious achievements! (Oh, wait—that’s Esquire.)

Meanwhile, New York magazine—a onetime rival that Spy spanked for “wandering off and getting lost among the boutique racks,” an observation still apt today—has gradually macrophaged so many design elements that Spy’s very ghost seems to be cackling within. All the more so because Mr. Andersen, after briefly editing New York in the late 1990’s, still contributes its “Imperial City” column. And Mr. Carter, as everyone knows, is now and forever in charge at Vanity Fair, also scorned by Spy back in the day. “Life is a cabaret, old chum,” they shrug in the introduction. After all, they had families to feed. It was time for The Serious Years.

But for a few brief shining moments in the early late 20th century, no one did the trivial pursuits of New York better—and New York then was really Manhattan, not Brooklyn, where Mr. Andersen lives (amusingly, Spy predicted that New York magazine would declare the Bronx the hot new neighborhood of the 1990’s). The magazine, so often accused of being “mean,” was really quite noble and idealistic in its devotion to reporting (albeit often under the comfortable cloak of pseudonym) and fact-checking and information, its “monkish, puckish will to utility,” as the authors put it (when Andy Warhol’s posthumous Diaries came out, they were the ones to assemble an index; would that someone had done the same here). There’s one thing the magazine was not, which so many are today, and that is lazy. It seems funny—you might even say ironic—to declare, but: Spy was industrious. Spy was generous. Spy was heartfelt. Spy was … inSpyring!

There’s also something great about having the white heterosexual man’s taste for gossip and the superficial, his ability to titter like an 18th-century courtier (“I always assumed, before I met Kurt and Graydon, that they’d be screaming queens,” says Henry Alford, a contributor), memorialized in hardcover book form. Ladies, they’re just like Us! (Yet another publication that owes much to Spy.)

“A hundred years from now,” went an early manifesto passed from Mr. Carter to Mr. Andersen, “the graduate student sifting through the racks at the New-York Historical Society will, with relish, throw himself upon old copies of Spy to get a feeling for what it was to be young and smart and living in New York in the eighties.” Ah, but why wait a hundred years to immortalize yourself when you can still be around to enjoy it? And yet it would’ve been so much more Spy to dash off a retrospective before the magazine even folded.

Spy: The Funny Years, by Kurt Andersen, Graydon Carter and George Kalogerakis. Miramax Books, 304 pages, $39.95. Hey! Remember Us?