Spy magazine existed during the ’80s mostly to ensure that Tama Janowitz didn’t get away with too much. You see, Tama Janowitz wrote novels that were more successful than their merit suggested they should be, so she needed to be put in her place. Thankfully, a bunch of jackasses with fancy educations who wished they were writing crappy books that sold a lot of copies were there to ridicule her. Take that, Tama Janowitz!

Seriously, Kurt Andersen and Graydon Carter chose just the right moment to publish Spy. New York was in the midst of a decade of greed that rivaled the Roaring Twenties for excess but with none of the earlier era’s panache. The publication was there to take the piss out of the whole stupid thing–the Milkens, the Helmsleys, the Trumps. (I will always feel indebted to Spy for dubbing Donald Trump a “short-fingered vulgarian.”) I can’t say I ever read the magazine much at the time, but the only things that came out of that decade that ended up influencing comedy more were Letterman and the Simpsons.

I got my grimy, grubby fingers on a copy of the October 1989 issue that is built around the “Spy 100,” the snarky mag’s annual takedown of insider traders, political advisors and all manner of irksome cretins that made NYC break out in hives. It features a fairly famous cover that shows President Bush (the sleepy one, not his son who gave the entire planet a vigorous rogering from behind) with words carved into his hair, as was the idiotic custom of some kids of the time. (The idea was later borrowed for this Newsweek cover.) The list skewers the expected (political hit-man Lee Atwater was number one), the unexpected (people excessively grieving the late Lucille Ball) and, yes, Tama Janowitz. An excerpt from the passage about hotelier horror Leona Helmsley:

“Caught billing more than $4 million in personal expenses to the real estate empire she gold-dug out of her now-enfeebled husband. Convicted of tax evasion (conspiracy and mail fraud; acquitted on charges of extortion of kickbacks from cowering business vendors). Continued running self-reverential ads. Anticipating the horror stories about her routine terorization of employees, Leona’s lawyer admitted in opening remarks–boasted even–that she was a ‘tough bitch.’ Trump called her a ‘disgrace to humanity in general.'”