[1][2] His novels The Postman Always Rings Twice (1934), Double Indemnity (1936), Serenade (1937), Mildred Pierce (1941) and The Butterfly (1947) brought him critical acclaim and an immense popular readership in America and abroad.

[3] Though Cain never delivered a successful Hollywood screenplay, several of his novels were made into highly regarded films, among them Double Indemnity (1944), Mildred Pierce (1945) and The Postman Always Rings Twice (1946).

His mother, Rose Mallahan—"small, pretty and very distinguished-looking"—had trained for seven years in her youth as a coloratura soprano and expected to pursue a career in opera after giving recitals in New Haven.

[16][14] While living in Chestertown, Cain recalled encountering a garrulous bricklayer, Ike Newton, who introduced the young student to the "language of an uneducated but articulate person."

Biographer Roy Hoopes traces Cain's fascination with common speech to this encounter, and compares it to the experiences of authors Jonathan Swift and Stephen Crane.

[17] By the age of 12, Cain was a "voracious" reader and familiar with the literary works of Edgar Allan Poe, William Thackeray, James Fenimore Cooper, Alexandre Dumas, Arthur Conan Doyle and Robert Louis Stevenson.

As an adult, according to biographer Roy Hoopes, "he came to regard the Church as one of the most ominous factors in all human history" and crafted his own independent view of "life and God."

Excelling in German and French language courses, his grades in Greek were mediocre; he passed his classes in "science, chemistry and Latin" but favored his coursework in history and literature.

[22] After moving to Baltimore to live independently, Cain engaged in desultory employment, working briefly as a ledger clerk for a public utility, then serving for two years as a road inspector for the State of Maryland.

[23] In his late teens, he frequented local brothels with male friends (Cain reports that he did not sleep with the prostitutes) and had a number of affairs with older women.

When he informed his family that he wished to pursue a career as a professional operatic singer, his mother, a trained soprano, emphatically vetoed him: "You have no voice, no looks, no stage personality.

[26] After quitting a low-paying job as a Victrola salesman, Cain abandoned his hopes of becoming a professional singer and committed himself to becoming a writer, receiving his parents' blessings.

[27][14] Biographer Roy Hoopes notes that Cain's postgraduate period was not "misspent": Almost everything Cain experienced in those four years of drifting around southern Maryland, Baltimore and Washington, D. C., played a part in his future fictional works; his frustrating job with insurance company contributed to Double Indemnity; construction work, which he learned about on the road commission, played an important role in his novels The Moth, Mignon, and Past All Dishonor; his brief music career contributed to his understanding of the singers in Serenade, Career in C Major, and Mildred Pierce; his Baltimore whorehouse nights were moved to Virginia City, Nevada, and put into Past All Dishonor, and his knowledge of southern Maryland and its people contributed background to his Galatea and The Magician's Wife.

He accepted a position as a math teacher in the autumn and registered for the draft when the United States entered World War I, but was initially rejected for respiratory disorders.

His first article, on a local drowning, so impressed the copy editor that Cain was instantly promoted to major assignments related to the war effort.

He was mustered out of the army on June 5, 1919, at Hoboken, New Jersey[38] Cain resumed working for The Baltimore Sun, serving as a copy editor at $30 a week in the post-war period.

[41][34] In early 1920 Cain became aware of the writing of the famed H. L. Mencken, editor of The Smart Set, "considered the most sophisticated magazine in the country at the time."

[42][34] In 1921 Cain covered the Bill Blizzard treason trial for the Sun in the aftermath of the Battle of Blair Mountain and the West Virginia coal mining labor struggles.

"[47] As his professional and personal alliance with Mencken deepened, Cain quit his teaching job at St. John's and committed himself solely to writing after moving to New York City.

[48] Cain's subject matter was characterized by scurrilous and humorous attacks on "American types and institutions...the pastor, county officials, town commissioners, and the whole concept of do-gooding service..." His 1925 Mercury dialogue "The Hero" exemplifies this style of satirical writing.

[55] Publisher and playwrights Philip Goodman and Vincent Laurence encouraged Cain to write a play about the evangelical Christian fundamentalism he had encountered during his reporting in West Virginia: Crashing the Gates opened in New England at Stamford and Worcester in February 1926 but closed after two weeks, receiving mixed reviews.

Critic Roy Hoopes writes: Cain learned what he could do pretending to be someone else, [but] the problem now was to translate this ability into writing about the people in whom he was most interested: the average men and women one reads about in the tabloids, the people who committed crimes of passion, who were victimized by the system, and who lived their lives unconcerned about what was going on in Washington D. C. or the board rooms on Wall Street..."[62][63]In 1930, a collection of Cain's dramatic dialogues and sketches was published in Our Government by Alfred A. Knopf publishers.

[64][65] When the New York World ceased publishing in 1931, Cain, on the recommendation of Morris Markey, was hired by Harold Ross to act as managing editor for The New Yorker.

[67][63] Hired by Paramount while the studio was entering bankruptcy, Cain was assigned to work on a remake of Cecil B. DeMille's The Ten Commandments (1923), but was dropped from the project after criticizing the story treatment of his supervisor.

After working on a script about novelist Harvey Fergusson's Hot Saturday (1926), Cain was terminated by Paramount in May 1932, confirming his "basic dislike of [motion] pictures.

"[68] Unemployed in 1932, Cain looked to the Southern California milieu for a short story and wrote "The Baby in the Icebox", which H. L. Mencken published in American Mercury.

Producer Jack Curtis Sr. bought the rights to the novel and director Robert B. Sinclair staged a theatrical adaptation of The Postman Always Rings Twice, opening in February 1936.

[75][76] Cain wrote a facsimile of Postman that published as a Liberty magazine serial in 1936: Double Indemnity, a love-murder conspiracy that unfolds in an insurance fraud.

[77][78] Cain's next literary project was 1938's Serenade, an opera-themed novel that addresses "the psychological sources of artistic power and creativity" and identifies heterosexuality as a sin qua non for success in the fine arts.

The Postman Always Rings Twice, The Butterfly, Serenade, Mildred Pierce, and Double Indemnity were published in one volume as The Five Great Novels of James M. Cain by Picador in 1985.