Willeford was born in Little Rock, Arkansas, in 1919. Following the death of his father from tuberculosis in 1922, Willeford and his mother moved to the Los Angeles area. After his mother's death in 1927, also from TB, he lived with his grandmother Mattie Lowey on Figueroa Street near Exposition Park until 1932. 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.
In March 1935, he signed up with the California National Guard; a few months later, he enlisted in the regular United States Army. He spent two years stationed in the Philippines serving as a fire truck driver, a gas truck driver, and briefly as a cook. At the end of 1938, he was discharged from the Army, though he re-enlisted in March 1939, joining the U.S. Cavalry stationed at the Presidio of Monterey, California. In the Cavalry, he learned to ride and care for horses and spent several months learning the art of horseshoeing. He also served as a "horseholder" in a machine gun troop and earned a marksman qualification.
In 1942, Willeford married Lara Bell Fridley before being stationed at Fort Benning, Georgia, for infantry school. He was assigned to the Third Army, Company C, 11th Tank Battalion, 10th Armored Division and sent to Europe as a tank commander. He fought in the Battle of the Bulge and earned the Silver Star, the Bronze Star for outstanding bravery, the Purple Heart with one oak leaf cluster, and the Luxembourg War Cross. After V-E day, he studied at Biarritz American University until he was shipped back to the United States.
Willeford again enlisted in 1945 for a term of three years. As a member of the 24th Infantry Division, he was stationed in Kyushu, Japan, from 1947 to 1949. He ran the Army radio station WLKH and was promoted to master sergeant.
His first book of poetry, Proletarian Laughter, was published in 1948. In May 1949, he and his wife, Lara, divorced. In July of the same year, he left the Army, leaving a mailing address of General Delivery, Dallas, Texas. He enrolled in the Universitarias de Belles Artes in Lima, Peru, studying art and art history in the graduate program. He was dismissed from the university when officials learned that he had neither an undergraduate degree nor a high school diploma. He lived in New York City for a month at the end of 1949 before re-enlisting in the Air Force.
Willeford was stationed at Hamilton Air Force Base in California through April 1952. He married Mary Jo Norton in July of that year, and lived for a while in Birmingham, Alabama. In 1953, Willeford's first novel, High Priest of California, was published. Bound as a double volume with another writer's novel, it sold 55,000 copies, about a third of its print run. In January 1954, he re-enlisted once again; he was stationed this time at Palm Beach Air Force Base, while living in West Palm Beach. In 1955, he was reassigned to Harmon Air Force Base in Newfoundland. Willeford finally left active duty in November 1956. By that time, two more novels of his had been published.
After retiring from the Air Force in 1956, Willeford held jobs as a professional boxer, actor, horse trainer, and radio announcer. He studied painting in France for a time, returning to the United States to attend Palm Beach Junior College. After receiving an associate degree in 1960, he studied English literature at the University of Miami, attaining a bachelor's degree in 1962 and a master's in 1964. 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. Willeford had been very productive as a novelist after leaving the military, but after 1962's Cockfighter, he would not have another novel published for nine years. 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 1971, The Burnt Orange Heresy, often identified as Willeford's best noir novel, and The Hombre from Sonora appeared (the latter under a pseudonym). Though he would continue to write fiction, there would again be an extended hiatus—thirteen years—before another novel of his came out. He wrote the screenplay for the 1974 film adaptation of Cockfighter, which he also acted in. In 1976, he and his second wife were divorced. The following year he appeared in a small role in the film Thunder and Lightning, produced by Roger Corman. Willeford married his third wife, Betsy Poller, in 1981. Three years later came the publication of Miami Blues, the first of the Hoke Moseley novels and their twisted take on the hardboiled tradition for which Willeford would become best known. The "series was almost nipped in the bud," notes Lawrence Block. 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." 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. Released in early 1988, it would be his last novel.
Charles Willeford died of a heart attack in Miami, Florida, on March 27, 1988, and is buried at Arlington National Cemetery.
Steve Erickson suggests that Willeford's crime novels are the "genre's equivalent of Philip K. Dick's best science fiction novels. They don't really fit into the genre." 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." "Quirky is the word that always comes to mind," according to crime novelist Lawrence Block. "Willeford wrote quirky books about quirky characters, and seems to have done so with a magnificent disregard for what anyone else thought." In Erickson's description, "The camera's not really focused on the middle of the scene. It's a little bit off. They're not plot driven or language driven, which makes them really different from most major crime novels. They're character driven and cunning in a very eccentric way." Lou Stathis argues that it is Willeford's "complete lack of sentimentality and melodrama that sets him apart from the pack of so-called 'tough-guy' writers.... Willeford's prose is as flat-toned and evenly cadenced—as emotionally neutral—as the blank visages of his feigned-human socio/psychopaths...the careful accretion of detail adding up to an incontrovertible truth of insight."
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.'" The Woman Chaser (1960), he writes, features a "structural self-consciousness [that] prefigures subsequent post-modernist texts." Lee Horsley describes how Willeford—along with his contemporaries Jim Thompson and Charles Williams—"structured entire narratives around the satiric presentation of the male point of view...subverting male stereotypes and creating a space within which the strong, independent woman could get and even sometimes keep the upper hand." David Cochran suggests that while his protagonists are not quite as psychotic as Thompson's, "they are in some ways even more disturbing because of their appearance of normality." 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."
Willeford's wide-ranging interests were reflected in his work: High Priest of California references T. S. Eliot, James Joyce's Ulysses, and composer Bela Bartok. The Burnt Orange Heresy cracks jokes about Samuel Beckett amidst contemplations of the sources of Dada and Surrealist painting. 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." 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. But even without such overt topicality, there was an ideological edge to his work. Cochran writes of the author's 1950s and 1960s novels,
Willeford created a world in which the predatory cannibalism of American capitalism provides the model for all human relations, in which the American success ethic mercilessly casts aside all who are unable or unwilling to compete, and in which the innate human appreciation of artistic beauty is cruelly distorted by the exigencies of mass culture.
In Haut's words, Willeford "creates characters who search for autonomy but settle for survival.... [He] never abandons his class perspective." 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." 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."
"Nobody writes a better crime novel," Elmore Leonard said of Willeford. 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." According to bookseller Mitch Kaplan, an expert on the South Florida literary scene, "Miami Blues launched the modern era of Miami crime fiction. There's a direct line from [Willeford] through just about everyone writing crime fiction in Miami today." 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." Daniel Woodrell is among the other crime novelists he is identified as influencing. Willeford's characteristic juxtaposition of humor and violence was apparently one of director Quentin Tarantino's inspirations. Discussing Pulp Fiction, Tarantino has said that the film "is not noir. I don't do neo-noir. I see Pulp Fiction as closer to modern-day crime fiction, a little closer to Charles Willeford." 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."
Three of Willeford's books have been adapted for the screen: Cockfighter (1974; starring Warren Oates and directed by Monte Hellman), for which Willeford wrote the screenplay; Miami Blues (1990; starring Alec Baldwin and directed by George Armitage); and The Woman Chaser (1999; starring Patrick Warburton and directed by Robinson Devor). Willeford adapted his first novel, High Priest of California, into a play. A 1988 production in New York City at The Vortex Theatre apparently represents its first full staging. A subsequent production was staged in 2003.