
John Cheever, whose short stories and novels earned him the nickname “the Chekhov of the Suburbs,” put Ossining on the literary map, setting some of his best-known stories in the thinly disguised town of Shady Hill.
The Pulitzer Prize-winning author lived and worked in a Dutch Colonial home on Cedar Lane, nicknamed “Afterwhiles,” from 1961 until his death in 1982, and set one of his novels in the fictional Falconer State Prison after he taught writing at Sing Sing.
Cheever’s eldest child, Susan Cheever, was witness to the origins of many of his stories, in which a daughter much like her is a recurring character.
Susan Cheever, herself a prize-winning author, recently published When All Men Wore Hats, which explores how everyday moments in her family’s lives provided grist for her father’s writings.
She will be appearing at Hudson Valley Books for Humanity in Ossining on Dec. 10 to talk about her book, which focuses on The Stories of John Cheever, published in 1978.
When All Men Wore Hats delves into some of John Cheever’s most famous short stories, including Goodbye My Brother, The Sorrows of Gin, The Five-Forty-Eight, The Housebreaker of Shady Hill, The Swimmer and Reunion.
John Cheever’s stories often suggest a lingering unhappiness lurking beneath the prosperity of Westchester County’s suburbs.
The Swimmer, which was made into a movie starring Burt Lancaster, follows the protagonist on a journey through his neighbors’ pools, only to arrive face-to-face with the emptiness of his life.
Susan Cheever calls her new book “a sequel of sorts” to her 1984 memoir, Home Before Dark, which drew upon memories, letters and journals to portray life with an immensely gifted but troubled father who wrestled with his drinking and sexuality.
In her new book’s prologue, Cheever tells of watching her father write his stories in their home’s dark guest room, “wearing a ragged crew neck sweater and hunched over a pile of cheap yellow paper.”
The book draws its title from her father’s preface to his collected short stories, which places his stories in “a long-lost world … when almost everybody wore a hat.”
The Cheevers first moved from Manhattan to the Scarborough hamlet of Briarcliff Manor in 1951, living in a cottage on Revolutionary Road that had once been home to author Richard Yates.
The family’s home on Cedar Lane was sold in 2016, two years after the death of Mary Cheever, John’s wife.
Susan Cheever’s published works include American Bloomsbury: Louisa May Alcott, Ralph Waldo Emerson, Margaret Fuller, Nathaniel Hawthorne and Henry David Thoreau; E.E. Cummings: A Life; My Name is Bill Wilson: His Life and the Creation of Alcoholics Anonymous; Drinking in America: Our Secret History; and the novels A Handsome Man and Doctors and Women.
At the Books for Humanity appearance, she will be joined by her brother, fellow writer and Pleasantville resident Ben Cheever, for a conversation about writing, the family legacy and the connections between art and life.
The book talk takes place from 6 to 7:30 p.m. on Dec. 10. Hudson Valley Books for Humanity at 67 Central Ave., Ossining. Visit hvbooksforhumanity.com to register for the program.

