[1] Willeford published steadily from the 1940s on, but vaulted to wider attention with the first Hoke Moseley book, Miami Blues (1984), which is considered one of its era's most influential works of crime fiction.

Film adaptations have been made of four of Willeford's novels: Cockfighter, Miami Blues, The Woman Chaser, and The Burnt Orange Heresy.

At the age of thirteen, in the midst of the Great Depression, he boarded a freight train in Los Angeles, assumed a false identity, and—passing as a seventeen-year-old—traveled by rail along the Mexican border for a year.

After retiring from the Air Force in 1956, Willeford held jobs as a professional boxer, actor, horse trainer, and radio announcer.

During this period he also worked as an associate editor with Alfred Hitchcock's Mystery Magazine and began a long tenure as a book reviewer for the Miami Herald.

Upon receiving his M.A., Willeford taught humanities classes at the University of Miami through 1967, then moved to Miami-Dade Community College where he became an associate professor, teaching English and philosophy through 1985.

In Willeford's first, unpublished sequel, "he had his unlikely hero commit an unforgivable crime, and ended the book with Hoke contentedly anticipating a life of solitary confinement.

"[6] As it turned out, the popularity of Miami Blues and its first two published sequels led to the largest financial windfall of the author's life: a $225,000 advance for the fourth Hoke Moseley book, The Way We Die Now.

"[9] Marshall Jon Fisher describes the "true earmark" of Willeford's writing, particularly his early paperbacks, as "humor—a distinctively crotchety, sometimes raunchy, often genre-satirizing humor.

"[11] Woody Haut suggests that Willeford's second novel, Pick-Up (1955), "combines David Goodis's romanticism, Horace McCoy's portrayal of alienated outcasts and Charles Jackson's depiction of life as a 'lost weekend.

"[15] Most, he points out, "have adjusted successfully to postwar American society, which given the[ir] psychotic nature...serves as a damning indictment of the dominant culture.

"[16] Willeford's wide-ranging interests were reflected in his work: High Priest of California references T. S. Eliot, James Joyce's Ulysses, and composer Béla Bartók.

In Block's words, "it is at once a solid crime novel and a fierce send-up of modern art while constituting perhaps the longest shaggy dog story ever told.

"[6] Willeford sometimes addressed more serious topics in explicit fashion: The Black Mass of Brother Springer (1958) is one of the first novels to depict the civil rights revolution that followed the Supreme Court's ruling in Brown v. Board of Education.

"[18] Describing the Hoke Moseley novels, Horsley similarly writes that Willeford "uses both his transgressors and his investigator...as commentators on the injustices of class and on a system that seems preoccupied with owning and controlling human life.

"[19] According to Willeford's wife, Betsy, he had a credo that also served as a caution for aspiring writers: "Just tell the truth, and they'll accuse you of writing black humor.

[20] Sean McCann credits Willeford—along with Jim Thompson and David Goodis—as one of the writers responsible for bringing the "hard-boiled crime story to a new stage in its development during the 'paperback revolution' of the 50s."

Centered around criminal protagonists rather than private eyes and "focused on those features of the genre that seemed most grotesque or cruel or uncanny and, extending them to new extremes, [they] remade the hard-boiled story into a drama of psychopathology.

"[7]: 117  Fellow writer James Lee Burke has acknowledged a "great debt" to Willeford: "If someone wanted advice about writing, about how to pull it off, make it work, punch it up ... Charles could tell you how to do it.

"[7]: 118  Writing in 2004, Jonathan Yardley of The Washington Post called him "one of our most skilled, interesting, accomplished and productive writers of what the literary establishment insists on pigeonholing as 'genre' fiction.