James M. Cain, the pioneer of the first-person confessional crime novel, was not a street-hardened brawler but a former choir boy and the son of a college president who dreamed of becoming an opera singer. His mother, a trained soprano, bluntly told him he lacked the talent, redirecting a life that seemed defined by disconnected failures.

Cain drifted through jobs as a ledger clerk, road inspector, and failed insurance salesman, survived a World War I gas attack, and worked in journalism before Hollywood fired him. In 1934 he channeled every failure into The Postman Always Rings Twice, followed by Double Indemnity and Serenade, converting his lived experience into dark, genre-defining fiction.

• A bricklayer named Ike Newton introduced him to the working-class slang he called the Vulgate.
• Skipping two grades left him social ...