Infinite jest

Assorted Spy covers skewering celebrities like Chevy Chase, Ivana Trump and Donald Trump. (Melcher Media/Miramax Books/HB Fenn)

The mid-eighties — an era in which Joe Piscopo headlined Hollywood movies and Ernest went to camp — were not exactly a boom time for comedy. Such was the crisis in funny that Billy Crystal’s You Look Mahvelous — an indescribably smarmy spinoff of the comic’s popular impression of Fernando Lamas on Saturday Night Live — became a hit song. Meanwhile, in America’s unofficial capital, New York, the go-go eighties had begun to really go. On any given evening, junk-bond billionaires and their collagen-enhanced companions rubbed shoulders with cravenly ambitious artists, hedonistic captains of industry, nouveau-riche jetsetters and, of course, Donald Trump. Clearly these people needed to be taken down a peg or two.

Years before Trump became associated with the phrase “You’re fired,” Spy magazine referred to him as the “short-fingered vulgarian.” Savvy, witty and merciless, Spy ridiculed the worst excesses of the age. In one of the magazine’s greatest pranks, cheques of increasingly negligible value were sent to prominent Americans in order to discover who was cheap enough to still cash them. (The two men who deposited 13-cent cheques were arms dealer Adnan Khashoggi and, yes, Trump.) “Speed-the-Play” parodied playwright David Mamet (Glengarry Glen Ross) by accelerating his rapid-fire dialogue until his plays could be performed in 60 seconds or less. The magazine’s japes also took the form of long essays, like the March 1989 issue’s takedown of “The Irony Epidemic” (a plague for which Spy was partially responsible). Then there were the small charts, lists or joke items like Separated at Birth that filled the magazine’s every nook and cranny.

Founded by Kurt Andersen and Graydon Carter, Spy pierced its targets with a ruthlessness rarely seen before or since in the American news media. In the words of writer Dave Eggers — who founded the Spy-like Might magazine before having greater success with the McSweeney’s empire — Spy was “cruel, brilliant, beautifully written and perfectly designed, and feared by all.” Minting a style and a tone that was widely emulated, Spy fostered talents who would go on to become Hollywood’s highest-paid screenwriters, producers on The Simpsons and editors of some of America’s biggest magazines.

Rogue agents: Spy co-founders Kurt Andersen (left) and Graydon Carter (middle), along with longtime editor George Kalogerakis. (Annie Leibovitz/Miramax Books)

The recently released compendium, Spy: The Funny Years, has a justly triumphant air, but there’s an undercurrent of wistfulness, too. While the magazine cultivated a brand of topical humour that reaches its current apotheosis in The Daily Show and The Colbert Report, the Internet and changes in the publishing business make an endeavour like Spy virtually impossible to repeat.

“People say, ‘Oh, couldn’t Spy exist now? Shouldn’t somebody start something like this?’” asks Kurt Andersen in a recent interview. “More power to them, and maybe they can. But it was easier to do a thing like this before there were hundreds of channels of every sort on the Internet, on cable, on everything else. And by doing it pretty well, frankly, we were able to get attention and have an impact that I don’t think would be possible today.”

Authored by Spy longtimer George Kalogerakis in collaboration with the founding editors, Spy: The Funny Years is an appropriately idiosyncratic combination of history, anthology and coffee-table book. Andersen and Carter met while toiling as journalists and editors at Time magazine. Born in Toronto, Carter had edited an Ottawa-based journal named The Canadian Review before moving to New York; the Nebraska-born Andersen had established his humour credentials by writing a self-help book parody called Tools of Power. Though neither was a native New Yorker, they hoped to flatter Manhattanites by creating a magazine that was as smart and sophisticated as they were (or thought they were).

After Carter, Andersen and their team scrabbled money together from a variety of investors, Spy published its first issue in October of 1986. Despite the magazine’s avid interest in all things New York, its wry tone had an appeal that extended far beyond the line-up at Elaine’s. Spy: The Funny Years is full of testimonials by kids in the sticks whose sensibilities were formed by the magazine. My own education began when I was browsing a Calgary newsstand in 1988 and saw the cover that featured supermodel Paulina Porizkova plucking a rat off her leg.

The magazine’s tone certainly had precedents in the history of humour writing: The New Yorker circa the 1930s, the British satirical journal Private Eye, the most scabrous prose of H.L. Mencken, P.G. Wodehouse and Tom Wolfe and the most anarchic moments of MAD. But Spy managed to do something that was both uncommon in its age and even rarer since. Not content to merely mock, many of the best pieces attached that snarky attitude to bona-fide investigative reporting. Andersen points to Philip Weiss’s November 1989 piece on the Bohemian Grove, a Northern California retreat that was a sort of summer camp for the world’s most powerful men. “That story is not about the most horrible thing on Earth, so to do it as a serious New York Times piece would be kind of ridiculous,” Andersen says now. “But it was a piece that deserved being done and with a certain sense of playfulness.”

(Melcher Media/Miramax Books/HB Fenn)

Andersen suggests that Spy’s doggedness — evident in the depth of research and handcrafted quality of the layouts — was partially what made the magazine unique. “We did devote vast, almost monkish energy and time to everything,” he says. The publication also existed in a far different era for gossip mongering. Spy’s potshots at the likes of Cher and Sylvester Stallone — as well as a scurrilous film-biz column by Celia Brady, an insider whose true identity was never revealed — made it a subject of awe and fear on the west coast. Andersen says the magazine had the advantage of arriving “when there weren’t hundreds of bloggers shooting spitballs at celebrity culture.” Moreover, “a certain amount of Spy-ish-ness hadn’t been absorbed by the straight celebrity magazines like Us Weekly. Not only was there less of the PR-armour fortress built around these people, but it was a rarer thing, and therefore more startling when we did it.”

Alas, Spy’s wit couldn’t stay razor-sharp forever. Despite the early success and strong circulation figures, financial instability eventually forced the team to seek out investors. Fractious relationships with a new owner led to the departure of Carter in 1991 and Andersen in 1993. Carter has been the editor of Vanity Fair since 1992; Andersen writes regularly for New York magazine, hosts the NPR show Studio 360 and will publish his second novel, Heyday, in March.

The magazine limped on in a somewhat desperate fashion for several years after Carter and Andersen’s departures. Though Spy: The Funny Years focuses on the Carter-Andersen era (hence the title), it does praise the attempts by final editor Bruno Maddox to revive some of the original spirit before the magazine finally expired in 1998.

By the late ’90s, Spy was decidedly old hat, supplanted by net-savvy publications like The Onion and Eggers’ McSweeney’s Internet Tendency. Then came the Sept. 11 attacks, a catastrophe that supposedly ended irony once and for all. Only, it didn’t. Over the course of this decade, the magazine’s DNA has been widely replicated in various snarky magazine items. Yet Andersen says he has an easier time recognizing Spy’s tone in The Daily Show than he does in print, largely because it’s become so difficult for humour journalism to keep up with TV and the movies. “Where did Borat begin?” asks Andersen rhetorically. “On cable. When we were doing Spy, cable barely existed in terms of original programming. So now, there are all these other places where pranks and stunts and Borat-like things can be done. It becomes hard for print to compete with that.”

Andersen did briefly dally with the idea of trying it all again after he became friends with Dave Eggers in the late ’90s. Says Andersen, “We would pretend as if there was a history, and that Spy and Might had merged in 1994 and kept publishing. This would be the new issue for 2001.”

Its name? Spite.

Jason Anderson is a Toronto writer.

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