His biographer, Francis Nevins Jr., rated Woolrich the fourth best crime writer of his day, behind Dashiell Hammett, Erle Stanley Gardner and Raymond Chandler.
Woolrich was born in New York City; his parents separated when he was young. He lived for a time in Mexico with his father before returning to New York to live with his mother, Claire Attalie Woolrich.
He attended Columbia University but left in 1926 without graduating when his first novel, Cover Charge, was published. As Eddie Duggan observes, "Woolrich enrolled at New York's Columbia University in 1921 where he spent a relatively undistinguished year until he was taken ill and was laid up for some weeks. It was during this illness (a Rear-Window-like confinement involving a gangrenous foot, according to one version of the story) that Woolrich started writing, producing Cover Charge, which was published in 1926." Cover Charge was one of his Jazz Age novels inspired by the work of F. Scott Fitzgerald. A second short story, Children of the Ritz, won Woolrich the first prize of $10,000 the following year in a competition organised by College Humor and First National Pictures; this led to his working as a screenwriter in Hollywood for First National Pictures. While in Hollywood, Woolrich explored his sexuality, apparently engaging in what Frances M. Nevins Jr. describes as "promiscuous and clandestine homosexual activity" and by marrying Violet Virginia Blackton, the 21-year-old daughter of J. Stuart Blackton, one of the founders of the Vitagraph studio. Failing in both his attempt at marriage and at establishing a career as a screenwriter (the unconsummated marriage was annulled in 1933; Woolrich garnered no screen credits), Woolrich sought to resume his life as a novelist:

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