Spy Magazine was a monthly satirical publication founded by Kurt Andersen, Graydon Carter, and Tom Phillips, in 1986. It was obsessed with wealthy people and decadence, especially in New York City. It distinguished itself from other publications in part because it measured the people it wrote about by a moral code, and was mercilessly harsh to those the editors found lacking.

They attacked people who were arrogant, venal, or stupid. Donald Trump was a particular enemy, though lesser known financiers, socialites, producers, and restaurateurs were mocked as well.

The magazine was famous in part for its cleverly edited covers (today we would call them "photoshopped", but the term did not yet exist when Spy started doing it). A photo of Hillary Clinton dressed as a dominatrix, for example, or Bruce Willis pregnant.

Their pranks are still being copied by other magazines. In one, they sent checks of gradually diminishing size to billionaires around the world, to determine scientifically which one was the world's cheapest plutocrat. (The answer, by the way, was that Adnan Khashoggi and Donald Trump tied by depositing checks for $0.13.) Spy writers attempted to reconstitute a twinkee from the ingredients listed on the side of the package. In a stunt since copied by many others, they would periodically call politicians, Hollywood directors, and media outlets, pretending to be various celebrities or other supposedly important people. They would time how long it took before they got called back, and use these times to calculate an aggregate "importance index". Sylvester Stallone, in one test, scored higher than any Senator or winner of the Nobel Peace Prize. From time to time, they would send checks from heinously-named foundations ("Friends of Sodomy") to various politicians, to see which would take the money.

They also originated the "Separated at Birth" feature, in which photographs of unrelated people are juxtaposed, and look surprisingly similar. Their pairing of Bette Davis with an evil tree from the Wizard of Oz is particularly well remembered.

Spy was not just pranks and insults, however. They commissioned serious investigations into corporations and organizations that they thought were corrupt (such as the Wackenhut Corporation and The Church of Scientology) and the resulting exposes are still cited when people discuss these outfits today.

The magazine was sold to new owners in 1991 and the founders left. It nearly died in 1994, but came back with a public announcement that the publishers had purchased a Russian tank on the black market and planned to come after anybody who gloated over their difficulties. The magazine folded for good in 1998. Most people think of Spy as a 1980s publication, one sign of how much better the early issues were than the later ones.

Kurt Andersen has gone on to write books, work as editor of New York Magazine, and found Inside.com, among other things. Tom Phillips was CEO of Deja.com and a venture capitalist. Graydon Carter is editor of Vanity Fair.

The following is, I believe, a comprehensive list of every issue of Spy Magazine, the name of the celebrity on the cover, and the main article. It is possible that I missed an issue or two, so if you find an error let me know. The "Spy 100" which appeared every year from 1987 was their catalogue of the "the worst people, places, and things of the year," supposed determined by a strictly objective formula. Donald Trump and, later, O.J. Simpson, would figure prominently in these lists.

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