His father was a prosperous shoe salesman, and Cheever spent much of his childhood in a large Victorian house , at Winthrop Avenue,  in the then-genteel suburb of Wollaston, Massachusetts. In the mids, however, as the New England shoe and textile industries began their long decline, Frederick Cheever lost most of his money and began to drink heavily. To pay the bills, Mary Cheever opened a gift shop in downtown Quincy—an "abysmal humiliation" for the family, as John saw it. 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.
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His father was a prosperous shoe salesman, and Cheever spent much of his childhood in a large Victorian house , at Winthrop Avenue,  in the then-genteel suburb of Wollaston, Massachusetts.
In the mids, however, as the New England shoe and textile industries began their long decline, Frederick Cheever lost most of his money and began to drink heavily. To pay the bills, Mary Cheever opened a gift shop in downtown Quincy—an "abysmal humiliation" for the family, as John saw it.
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.
His grades continued to be poor, however, and, in March , he was either expelled for smoking or more likely departed of his own accord when the headmaster delivered an ultimatum to the effect that he must either apply himself or leave.
The year-old Cheever wrote a sardonic account of this experience, titled "Expelled", which was subsequently published in The New Republic.
Cheever spent the summer of at Yaddo, which would serve as a second home for much of his life. Cheever drove from one place to another in a dilapidated Model A roadster, but had no permanent address. Maxim Lieber became his literary agent, — 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.
Watson , an assistant to Alexander Graham Bell during the invention of the telephone. They married in Cheever enlisted in the Army on May 7, His first collection of short stories, The Way Some People Live, was published in to mixed reviews. Cheever himself came to despise the book as "embarrassingly immature", and for the rest of his life to destroyed every copy he could lay his hands on.
Meanwhile, most of his old infantry company was killed on a Normandy beach during the D-Day invasion. 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 , though the magazine did not make space for it until five years later.
Largely on the strength of these two stories still in manuscript at the time , Cheever was awarded a Guggenheim Fellowship. Vanderlip, a banker,  in the Westchester hamlet of Scarborough-on-Hudson , where he rented a small cottage on the edge of the estate. The house, coincidentally, had been occupied before the Cheevers by another suburban chronicler, Richard Yates. 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.
In the summer of , a screen adaptation of "The Swimmer", starring Burt Lancaster , was filmed in Westport, Connecticut. Cheever was a frequent visitor on the set, and made a cameo appearance in the movie.
Still, he blamed most of his marital woes on his wife, and in he consulted a psychiatrist, David C. Hays, about her hostility and "needless darkness. At the joint session, however, Hays said as Cheever noted in his journal that Cheever himself was the problem: "a neurotic man, narcissistic, egocentric, friendless, and so deeply involved in [his] own defensive illusions that [he has] invented a manic-depressive wife.
But in the gluey atmosphere of Bullet Park no birds sing. He began an affair with actress Hope Lange in the late s. After a month in the hospital, he returned home vowing never to drink again; however, he resumed drinking in August. 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.
Driven home by his wife on May 7, Cheever never drank alcohol again. The Stories of John Cheever appeared in October , and became one of the most successful collections ever, selling , copies in hardback and winning universal acclaim. The contract led to a long legal battle and a book of 13 stories by the author entitled Fall River and Other Uncollected Stories, published in by Academy Chicago Publishers. This was parodied to comedic effect in a episode of the TV sitcom Seinfeld , when the character Susan discovers explicit love letters from Cheever to her father.