Jonathan Taylor writes:

[Update: Back Issues locates an even earlier use of the word "asshole" in The New Yorker, in 1975, among other corrections to Green's list.]

Bookforum corrects the assertion by Elon Green in The Awl that the word "asshole" was first used in The New Yorker in 1994 (as you would gather from the mag's own site search). In fact, the word "assholes" is believed to have debuted in a quote in an October 20-27, 1986, two-part Profile by everyone's favorite antijournalist, Janet Malcolm, "A Girl of the Zeitgeist."

The "Girl" in question was Ingrid Sischy, editor of Artforum. This portrait of the "art world" through Sischy--herself a curiously fleeting presence in her own profile--drew a response (also two-part) by the Village Voice's art critic at the time, Gary Indiana, subtitled "Breaking the Asshole Barrier." He wrote, "The maiden appearance of the word 'asshole' is the least distressing infelicity in Malcolm's article, but in the context of The New Yorker it seems portentous of the shape of things to come."

In part one, Indiana dissected what he calls Malcolm's "trial-by-interior," in which she communicated her estimates of her interlocutors through her admiration, or lack thereof, of their domestic spaces: Rosalind Krauss, utterer of the word "assholes," lives in "one of the most beautiful living places in New York."

Artists themselves, Indiana said, didn't come off so well in Malcolm's method: Sherry Levine told him, "I knew nothing good was coming when the fact checker from The New Yorker called to ask me if it would be accurate to say that my bathtub is in the kitchen and I live alone with my cat," and asked Levine to define "railroad apartment."

(Malcolm also somewhat famously critiqued Sischy's style of chopping tomatoes: "She took a small paring knife and, in the most inefficient manner imaginable, with agonizing slowness, proceeded to fill a bowl, tiny piece by tiny piece, with chopped tomatoes. Obviously, no one had ever taught her the technique of chopping vegetables, but this had in no way deterred her from doing it in whatever way she could or prevented her from arriving at her goal.")

The other "famous story" about profanity in The New Yorker, of course, is Norman Mailer declaring that "true liberty" meant the "right to say shit in The New Yorker."