Since the book's publication, Holden has become an icon for teenage rebellion and angst, and is considered among the most important characters of 20th-century American literature.

The novel recounts Holden's week in New York City during Christmas break, circa 1948/1949, following his expulsion from Pencey Prep, a preparatory school in Pennsylvania based loosely on Salinger's alma mater Valley Forge Military Academy.

Holden Caulfield tells his story with surprising honesty from a sanatorium in California in a cynical and jaded language.

Several early pieces featuring Holden Caulfield formed the basis of parts of Catcher in the Rye, but were rewritten for the novel.

The character, as Holden Caulfield, appears in Salinger's "Slight Rebellion off Madison", published in the December 21, 1946, issue of The New Yorker.

An edited version of this short story later became the basis of several chapters in the middle-late section of The Catcher in the Rye dealing with Caulfield's date with Sally Hayes, during which he confesses his desire to run away with her, meets Carl Luce for drinks, and makes a drunken phone call to the Hayes' home.

Unlike the similar sequence in the novel, Caulfield is on a Christmas break from school, and, in the story, the interlude with Sally is split into two occurrences.

Caulfield also figures as a character in the short story "I'm Crazy", published in Collier's (December 22, 1945), and other members of the Caulfield family are featured in "Last Day of the Last Furlough", published in The Saturday Evening Post (July 15, 1944) and the unpublished short stories "The Last and Best of the Peter Pans" (c. 1942) and "The Ocean Full of Bowling Balls" (c. 1945).

It begins with Caulfield standing on a hill at Pencey Prep watching a football game below, and develops as Holden visits with his history teacher, Mr. Spencer, for a talk about his expulsion from school and his future.

The events occur just after the death of Kenneth (later renamed Allie) and reveal the anxiety of Mary Moriarity, an actress and Caulfield's mother.

[citation needed] Another short story of note with relationship to Caulfield is "The Boy in the People Shooting Hat", which was submitted to The New Yorker sometime between 1948 and 1949 but was never published.

In "The Stranger", published in Collier's December 1, 1945, Babe Gladwaller and his sister Mattie (a prototype for Phoebe) visit Vincent Caulfield's former girlfriend, now married, to tell her about his death and deliver a poem he wrote about her.

for their second studio album, Kerplunk (1991) after lead singer and guitarist Billie Joe Armstrong read The Catcher in the Rye.