Around this time, Cheever's older brother Fred—recalled from Dartmouth in 1926 because of the family's financial crisis—reentered his life "when the situation was most painful and critical," as John later wrote. After the bankruptcy (in 1932) of Kreuger and Toll International Match, in which Frederick Cheever had invested what was left of his money, the Cheever house on Winthrop Avenue was lost to foreclosure. The parents separated, while John and Fred took an apartment together on Beacon Hill in Boston. 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. Ames denied his first application, but offered him a place the following year, whereupon Cheever decided to sever his "ungainly attachment" to his brother. (Passages in Cheever's journal suggest—without stating conclusively—that his relationship with Fred may have been sexual.) Cheever spent the summer of 1934 at Yaddo, which would serve as a second home for much of his life.
Cheever enlisted in the Army on May 7, 1942, and his first collection, The Way Some People Live, was published the following year 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, where he commuted via subway from his apartment in Chelsea: meanwhile, most of his old infantry company was killed on 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 Fifty-ninth Street, near Sutton Place; 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 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 many critics), 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 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, where Cheever was a frequent visitor on the set and did a cameo for 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, Dr. 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.
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) 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.
During a teaching junket at the University of Utah in January 1977, Cheever met a Mormon writing student named Max, who for the next five years would be an occasional companion, secretary, and (somewhat reluctantly) lover. Two months later, Cheever appeared on the cover of Newsweek magazine with the caption, "A Great American Novel: John Cheever's 'Falconer.'" The novel was Number One 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.
After Blake Bailey published his biography of Richard Yates, A Tragic Honesty (2003), Cheever's son Ben suggested he write an authoritative biography of Cheever. The book will be published by Knopf in 2009.