The 1980s were golden for satirists in New York City, as blowhard personalities such as mayor Ed Koch, the Yankees’ George Steinbrenner and garish hustler Donald Trump dominated the mediascape. Celebrity headliners from Spike Lee and Madonna to Darryl Strawberry also crowded the tabloid fronts.

Upstart  magazine Spy took full aim, with a brazen style that was not intimidated by celebrity.  A look back at these pioneer Trump-baiters who, long before Twitter, were eager to pierce wealth-and-fame bubbles.

Like many hardcore Spy fans, I pulled out my archives to look back at the magazine’s coverage of Donald Trump after his improbable escalator descent in June 2015. — How did this guy get here?

That question was  asked pointedly by the editors of Spy in the late 1980s and early 1990s. Trump was mocked and his pretensions were derided, often in language the young tycoon was unlikely to grasp.  One letter-writer, copying the Spy neutral-chronicler tone, noted that the magazine contained one mention of Trump every 25.6 pages which, given its 96-page binding, meant about 4 pages per issue with Trump content. An “omni-feuder”, as Spy rightly labelled him, Trump took note and often dispatched short, threatening letters with specious references to future court appearances to the editors. These included Canadian expat Graydon Carter. Non-plussed, Spy just annotated and published the Trump notes.

There were memorable misses — one investigative feature on Trump’s financial state and plunging fortunes was titled “The last feature you will ever have to read on Donald Trump”. But more often its portrayals of the “short-fingered vulgarian” proved accurate and enduring.

For my generation of boomers, Spy was part of a progression of humour from the ’60s guffaws in pre-teen Mad magazine to the darker and more radical National Lampoon of the 1970s. By the late 1980s the boomers had arrived economically, and many were horrified at the grasping, status-driven behaviour of their peers, the notorious yuppies. From this reaction, and in a city culture bathed in Lettermanesque irony, was born Spy.

In 1989, I contacted Carter for a profile in the Montreal Gazette, a piece which I recently recovered and now reprint below. Surprisingly, Trump was not his main focus. Worth rereading for that alone.

In 2016, after Trump emerged as a serious political force, several publications, including Graydon Carter’s long-time vehicle Vanity Fair, looked back on that raucous Spy-Trump relationship. The best of these retrospectives appeared in the Bowery Boys New York history site, linked here: http://www.boweryboyshistory.com/2015/08/spy-vs-trump-the-best-donald-trump-moments-from-spy-magazine-1986-98.html

UPDATE, Aug 13, 2018: One criticism levelled at Carter during his stay at Vanity Fair, is that he edited VF in some of the ways that he warned against in our 1990 Gazette interview: loads of celebrities, but in a medium that often could not allow itself to ridicule their self-absorbed opinions. Other editors will now have a go at taming the wilds of Hollywood: https://www.nytimes.com/2017/11/13/business/radhika-jones-vanity-fair.html

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In a very unfair stunt, Spy issued a cheque for 13 cents to see if Trump would cash it. He did. (Spy, July 1990)

I SPY

We don’t pick on the little people, says Spy editor Carter, we go after the overdogs

By David Winch, The Gazette, June 3 1990 

The rich and famous got great press during the Reagan era, a time when Esquire magazine could unashamedly trumpet on its cover: “SUCCESS! The Religion of the ’80s”.

Pop culture embraced the cult of “success” with verve. TV’s Entertainment Tonight made self-promotion easy and profitable for celebrities, and set the tone for much of the media.

Michael J. Fox’s Alex Keaton character and Madonna’s “material girl” vaunted the joy of money, while real-life tycoons Malcolm Forbes and Donald Trump popped up on magazine covers everywhere for having achieved the fast-track dream – great wealth and fame.

But, hey – who wouldn’t go for it, if he or she had the chance?

Somehow, Spy magazine didn’t buy that attitude.

In fact, after a decade of celebrity adulation the maverick publication set out to put some bite back into coverage of the famous.

One early Spy cover showed Donald Trump falling on his rear end and its writers often labelled him a “short-fingered vulgarian,” making it clear the editors would take a sharply critical view of the rich and famous.

This irreverence helped make the acerbic and very funny little New York magazine a hit, by holding the spotlight up to the seamy underside of North America’s new aristocracy – celebrities.

“We don’t pick on the little people,” says Canadian-born E. Graydon Carter, a founding editor of Spy.

“We go after the overdogs.”

Want to know

Sure enough, the magazine has been obsessed with “wife-dumping Atlantic City strongman” Trump, who Spy takes as a symbol of the vulgarity and publicity-hunger of America’s celebrity class.

But Spy also highlights – in amazingly frank and detailed reports – all manner of low-life incidents among the famous: Hollywood agents’ lechery, stars’ embarrassing foibles and taboo misadventures among public figures.

After all, lots of readers want to know:

* Who exactly has Warren Beatty slept with?

* How contemptuously does Bianca Jagger treat waiters?

* What does rising-star writer Jay McInerney’s wife think of him as they head to divorce court?

* How do New York’s stars furnish their summer homes, and how obnoxious are they to their country neighbors?

* What precise words does top Hollywood agent Mike Ovitz use to dress down his top client?

* And who’s up and who’s down inside the world’s most powerful newspaper, the New York Times?

Some of Spy‘s regular features have been widely talked about – and imitated. These include Separated at Birth, which juxtaposes pictures of pairs of celebrities whose resemblance is distinctly unflattering for one of them, but also very funny.

Spy is also packed with silly-looking charts and graphs highlighting everything from the rise and fall of media stars’ careers, to the number of nose jobs or tummy tucks certain Hollywood celebrities have had.

One monthly column gives detailed inside information about the lives of the top editors at the New York Times, a column obviously gleaned from an extensive network of willing informants. Another feature, the Spy List, looks as if it is simply a list of famous names. But by piecing together similarities as in a cryptic code, the reader can often get shockingly intimate information.

Hip and smart

Spy carries out this reporting with rigorous standards of fact- checking: as a result, the often-scathing magazine has never been sued, despite publishing what the Wall Street Journal recently blasted as “assassination pieces.”

Editorially, Spy has opened up unexplored territory since its launch in 1987 – it has combined the titillation of the supermarket tabloids with a hip, young middle-class readership, one that’s eager for smartly written articles deflating and ridiculing the famous.

Consequently, Spy has been called the “National Enquirer of the Chablis-and-brie set.”

The magazine is also visually distinctive – full of little pictures and different typefaces jumping all over the page. While some readers find the look refreshing, others complain that it’s simply confusing.

Spy has been a modest circulation success on the newsstands with sales figure of 133,000 monthly, 28 per cent of which are sold in New York City. It has developed a devoted, almost cult following. “I think a very high percentage of our readers say this is their favorite magazine,” said Carter, 40, who lives in West Side Manhattan, with his wife and three children.

This devotion has established Spy as a hot advertising vehicle for urban professionals – Wall St. firm Morgan Stanley is now seeking new investors for the magazine, and seven-figure sums are obligatory to get in on the action.

On Wednesday, April 18, Spy launched a new phase of its growth, with a TV special on NBC emceed by Jerry Seinfeld on the theme “How to Be Famous.”

The cast of the satirical special included Victoria Jackson and Harry Shearer, with brief appearances by the Smothers Brothers, Joe Namath, Ricardo Montalban and Dick Cavett.

NBC entertainment chief Brandon Tartikoff compared the Spy special to the launch of Saturday Night Live or David Letterman’s late-night show.

But the special may instead have highlighted how much Spy is tied to its magazine format.

Using a mock-documentary style, Seinfeld narrated a tongue-in-cheek report on the world of celebrities, including a five-step guide to getting famous in the first place (talent is optional, but having “handlers” is essential).

The pace of How to be Famous, however, was too slow for television. Zippy one-liners that might have worked in a wordy magazine piece, came off as limp on TV. Some stunts were amusing, such as comparing the reaction that fading celebrities Tom and Dick Smothers got walking down Fifth Ave. in New York with that of a dress-up rabbit and a walking radish. (The rabbit and radish got more attention.) Or nationwide poll results about whether Americans believed Marie Osmond was dead or alive. (She’s still alive, apparently).

But the magazine’s great strengths – its insider tone and polished writing – were lost in the attempt to reach a mass, prime-time network audience. Spy will have to get funnier or focus on much tighter audience niches to make any progress on TV.

Like David Letterman, Spy‘s skeptical style combined with its irreverent humor has proven popular with baby-boomers.

No access

Carter links this to disillusion with the fawning coverage stars have received in recent years, when TV shows like Entertainment Tonight erase completely the line between journalism and public relations.

He puts the blame on People magazine.

“In post-People journalism, celebrity profiles became the staple of magazines,” says the Ottawa native, who left Canada and started at Time in the late 1970s. There, he wrote for the People section that inspired the magazine spinoff.

People magazine’s emphasis on celebrity profiles, said Carter, “greatly increased competition among magazines to see who could get which star on their covers … and since celebrities could control access by refusing an interview, they progressively gained more control over what was published.

“(Celebrities) wanted – and got – rights to approve the writer, the photographer, whether there was a cover picture, and so on. Because if you have Madonna on your magazine’s cover, you sell more copies.

“Spy was designed so that we don’t have to have that kind of access.”

Coincidentally, when The Gazette interviewed Carter [in May 1990], Madonna was gracing the cover of Vanity Fair.

“It (Vanity Fair) symbolizes what you could call ‘the pornography of success,’ which implies that a man’s worth equals his press coverage,” said Carter.

“Instead, we try to hold the ‘winners’ up to the light. And to do it with some humor.”

Being a Canadian has strongly influenced his reaction to New York, said Carter. He said he felt shocked, but fascinated, by the excess, shamelessness, greed and venality of the rich and famous there.

“We have a more delicate sensibility, I think. Wealth is much more discreet in Canada; when I saw how Trump was treated as a savior in the mid-’80s, I found it unbelievable,” he said.

Unlike National Lampoon, which shone briefly with a particularly lacerating brand of humor in early-1970s, then faded, Spy’s editors expect the magazine to thrive into the 1990s.

“If we work hard, I think readers will always seek us out, like a good restaurant. We’ve tapped a market for funny journalism that’s always there. Every day I pinch myself … Jesus, it’s fun!

“And in New York, of course, there’s never a shortage of characters (to lampoon) … that’s just not a problem.”

© 1990 Postmedia Network Inc. All rights reserved.