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. Cheever drove from one place to another in a dilapidated Model A roadster, but had no permanent address. In 1935, Katharine White of The New Yorker bought Cheever's story, "Buffalo," for $45—the first of many that Cheever would publish in the magazine. Maxim Lieber became his literary agent, 1935-1941. In 1938, he began work for the Federal Writers' Project in Washington, D. C., which he considered an embarrassing boondoggle. 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." He quit after less than a year and a few months later he met his future wife, Mary Winternitz, seven years his junior. 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. The couple married in 1941.
Cheever enlisted in the Army on May 7, 1942. His first collection of short stories, The Way Some People Live, was published in 1943 to mixed reviews. Cheever himself came to despise the book as "embarrassingly immature," and for the rest of his life endeavored to destroy every copy he could lay his hands on. The book arguably saved his life, however, when it fell into the hands of Major Leonard Spigelgass, an MGM executive and officer in the Army Signal Corps, who was struck by Cheever's "childlike sense of wonder." Early that summer, Cheever was transferred to the former Paramount studio in Astoria, Queens, New York City, where he commuted via subway from his apartment in Chelsea, Manhattan, New York City. Meanwhile, most of his old infantry company was killed on a Normandy beach during the D-Day invasion. Cheever's daughter Susan was born on July 31, 1943.
After the war, Cheever moved his family 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. In 1946, he accepted a $4,800 advance from Random House to resume work on his novel, The Holly Tree, which he had discontinued during the war. "The Enormous Radio" appeared in the May 17, 1947, issue of The New Yorker — a Kafkaesque tale about a sinister radio that broadcasts the private conversations of tenants in a New York apartment building. 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." Cheever's son Benjamin was born on May 4, 1948.
Cheever's work became longer and more complex, apparently a protest against the "slice of life" fiction typical of The New Yorker in those years. 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. In 1951, Cheever wrote "Goodbye, My Brother," after a gloomy summer in Martha's Vineyard. Largely on the strength of these two stories (still in manuscript at the time), Cheever was awarded a Guggenheim Fellowship. On May 28, 1951, Cheever moved to Beechwood, the suburban estate of Frank A. 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. In Scarborough, he was a casual volunteer for the Briarcliff Manor Fire Department.
Cheever's second collection, The Enormous Radio, was published in 1953. 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. Meanwhile, Random House demanded that Cheever either produce a publishable novel or pay back his advance, whereupon Cheever wrote Mike Bessie at Harper & Brothers ("These old bones are up for sale"), who bought him out of his Random House contract. In the summer of 1956, Cheever finished The Wapshot Chronicle while vacationing in Friendship, Maine, and received a congratulatory telegram from William Maxwell: "WELL ROARED LION." With the proceeds from the sale of film rights to "The Housebreaker of Shady Hill", Cheever and his family spent the following year in Italy, where his son Federico was born on March 9, 1957 ("We wanted to call him Frederick," Cheever wrote, "but there is of course no K in the alphabet here and I gave up after an hour or two").
The Wapshot Scandal was published in 1964, and received perhaps the best reviews of Cheever's career up to that point (amid quibbles about the novel's episodic structure). Cheever appeared on the cover of Time magazine's March 27 issue, this for an appreciative profile, "Ovid in Ossining." (In 1961 Cheever had moved to a stately, stone-ended Dutch Colonial farmhouse in Ossining, on the east bank of the Hudson.) "The Swimmer" appeared in the July 18, 1964 issue of The New Yorker. 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 1966, 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.
By then Cheever's alcoholism had become severe, exacerbated by torment concerning his bisexuality. Still, he blamed most of his marital woes on his wife, and in 1966 he consulted a psychiatrist, David C. Hays, about her hostility and "needless darkness." After a session with Mary Cheever, the psychiatrist asked to see the couple jointly; Cheever, heartened, believed his wife's difficult behavior would finally be addressed. At the joint session, however, Hays claimed (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." Cheever soon terminated therapy.
Later life and career
Bullet Park was published in 1969, and received a devastating review from Benjamin DeMott on the front page of The New York Times Book Review: "John Cheever's short stories are and will remain lovely birds... But in the gluey atmosphere of Bullet Park no birds sing." Cheever's alcoholic depression deepened, and in May he resumed psychiatric treatment (which again proved fruitless). He began an affair with actress Hope Lange in the late 1960s.
On May 12, 1973, Cheever awoke coughing uncontrollably, and learned at the hospital that he had almost died from pulmonary edema caused by alcoholism. After a month in the hospital, he returned home vowing never to drink again; however, he resumed drinking in August. Despite his precarious health, he spent the fall semester teaching (and drinking, both with fellow writer-teacher, Raymond Carver) 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. On April 9, Cheever was admitted to the Smithers Alcoholic Rehabilitation Unit in New York, where he shared a bedroom and bath with four other men. Driven home by his wife on May 7, Cheever never drank alcohol again.
In March 1977, Cheever appeared on the cover of Newsweek with the caption, "A Great American Novel: John Cheever's Falconer." The novel was #1 on the New York Times Best Seller list for three weeks. The Stories of John Cheever appeared in October 1978, and became one of the most successful collections ever, selling 125,000 copies in hardback and winning universal acclaim.
Cheever was awarded the Edward MacDowell Medal for outstanding contribution to the arts by the MacDowell Colony in 1979.