It was Chabon's first novel, which he began writing when he was a twenty-one-year-old undergraduate at the University of Pittsburgh. He continued to work on it during his studies (1985 - 1987) in the Creative Writing Program of the Department of English at the University of California, Irvine, where he submitted it as his thesis for the Master of Fine Arts degree. One of his advisors, the novelist MacDonald Harris, sent it to his literary agent. It was published in 1988 and became a bestseller.
The novel tells the story of Art Bechstein, the son of a mob money launderer who falls into a love triangle with a charming young man, Arthur Lecomte, and a beguiling young woman named Phlox Lombardi. A subplot concerns the highly literate biker Cleveland Arning and his would-be career as a jewel thief.
The novel takes place during summer. It begins in April, just after Bechstein has finished his four-year undergraduate education at the University of Pittsburgh. Specific settings include Carnegie Mellon University, Chatham College, Hillman Library, Lake Erie, Presbyterian University Hospital, Schenley Park, Schenley Bridge, and the Pittsburgh neighborhoods of Oakland, Squirrel Hill, Shadyside, Downtown, Mount Washington, East Liberty, Fox Chapel, and Highland Park. A boiler plant, informally labeled The Cloud Factory, located in Junction Hollow between Carnegie Mellon University and the Carnegie Museums of Pittsburgh, plays a special role in the novel.
A recently-reissued edition of the book featured an author's note in the back; entitled "P.S.", it details some of the inspiration, problems and process by which the novel was written. For example, when writing portions of the novel, he often had to balance his early-model computer precariously on an old tool table to type properly. Many fans of his work had questioned Chabon's sexuality, due to the presence of gay characters in his novels. On page twelve of the expanded notes section he reveals that, although he is currently married to a woman, he has had same-sex relations in the past.