[1][2] His fiction is mostly set on the Upper East Side of Manhattan; the Westchester suburbs; old New England villages based on various South Shore towns around Quincy, Massachusetts, where he was born; and Italy, especially Rome.

Many of his works also express a nostalgia for a vanishing way of life (as evoked by the mythical St. Botolphs in the Wapshot novels), characterized by abiding cultural traditions and a profound sense of community, as opposed to the alienating nomadism of modern suburbia.

His father was a prosperous shoe salesman, and Cheever spent much of his childhood in a large Victorian house, at 123 Winthrop Avenue,[5] in the then-genteel suburb of Wollaston, Massachusetts.

[6] In 1926, Cheever began attending Thayer Academy, a private day school, but he found the atmosphere stifling and performed poorly, and finally transferred to Quincy High in 1928.

A year later, he won a short story contest sponsored by the Boston Herald and was invited back to Thayer as a "special student" on academic probation.

In 1933, John wrote to Elizabeth Ames, the director of the Yaddo artist's colony in Saratoga Springs, New York: "The idea of leaving the city", he said, "has never been so distant or desirable.

[citation needed] For the next few years, Cheever divided his time between Manhattan, Saratoga, Lake George (where he was caretaker of the Yaddo-owned Triuna Island), and Quincy, where he continued to visit his parents, who had reconciled and moved to an apartment at 60 Spear Street.

As an editor for the WPA Guide to New York City, Cheever was charged with (as he put it) "twisting into order the sentences written by some incredibly lazy bastards.

[10] She was a daughter of Milton Winternitz, dean of Yale Medical School, and granddaughter of Thomas A. Watson, an assistant to Alexander Graham Bell during the invention of the telephone.

However, the book may have saved his life after falling into the hands of Major Leonard Spigelgass, an MGM executive and officer in the Signal Corps, who was struck by Cheever's "childlike sense of wonder.

After the war, Cheever and his family moved to an apartment building at 400 East 59th Street, near Sutton Place, Manhattan; almost every morning for the next five years, he would dress in his only suit and take the elevator to a maid's room in the basement, where he stripped to his boxer shorts and wrote until lunchtime.

A startling advance on Cheever's early, more naturalistic work, the story elicited a fan letter from the magazine's irascible editor, Harold Ross: "It will turn out to be a memorable one, or I am a fish.

An early draft of "The Day the Pig Fell into the Well"—a long story with elaborate Chekhovian nuances, meant to "operate something like a rondo", as Cheever wrote to his friend and New Yorker editor William Maxwell—was completed in 1949, though the magazine did not make space for it until five years later.

Reviews were mostly positive, though Cheever's reputation continued to suffer because of his close association with The New Yorker (considered middlebrow by such influential critics as Dwight Macdonald), and he was particularly pained by the general preference for J. D. Salinger's Nine Stories, published around the same time.

Cheever noted with chagrin that the story (one of his best) appeared toward the back of the issue—behind a John Updike story—since, as it happened, Maxwell and other editors at the magazine were a little bewildered by its non-New Yorkerish surrealism.

Despite his precarious health, he spent the fall semester teaching (and drinking, both with fellow writer-teacher, Raymond Carver[20]) at the Iowa Writers' Workshop, where his students included T. C. Boyle, Allan Gurganus, and Ron Hansen.

As his marriage continued to deteriorate, Cheever accepted a professorship at Boston University the following year and moved into a fourth-floor walkup apartment at 71 Bay State Road.

Cheever's drinking soon became suicidal and, in March 1975, his brother Fred, now virtually indigent, but sober after his own lifelong bout with alcoholism, drove John back to Ossining.

"[29][30] In the summer of 1981, a tumor was discovered in Cheever's right lung, and, in late November, he returned to the hospital and learned that the cancer had spread to his femur, pelvis, and bladder.

The contract led to a long legal battle, eventually resulting in Thirteen Uncollected Stories by John Cheever, published in 1994 by Academy Chicago.

Susan's memoir, Home Before Dark (1984), revealed Cheever's sexual relationships with both women and men, which was confirmed by his posthumously published letters and journals.