Wilson attracted attention from readers with aggressively violent and sexually explicit panoramas of lowlife denizens, often depicting the wild escapades of pirates and bikers.
As James Danky and Denis Kitchen wrote in their book, Underground Classics, "He astonished and sometimes frightened his fellow cartoonists, though they saw it as pushing if not eviscerating the boundaries of taste.
Wilson's later work became more ghoulish, featuring zombie pirates and visualizations of Our Lady of Guadalupe as a rotting vampire mother.
Wilson was also a frequent contributor to Arcade, edited by Art Spiegelman and Bill Griffith; as well as Weirdo, Crumb's post-underground anthology published in the 1980s and early 1990s.
[citation needed] The Art of S. Clay Wilson, published in 2006 by Ten Speed Press, covers his prints and paintings as well as his comics work.
In 1994, he began interpreting classic children's stories, illustrating Hans Christian Andersen and the Brothers Grimm, as he explained to interviewers Jon Randall and Wesley Joost: The stories in Wilson's Grimm (Cottage Classics, 1999) are "Snow White", "The Spirit in the Bottle", "The Valiant Little Tailor", "The Devil with the Three Gold Hairs", "Hansel and Gretel", "Bearskin" and "The Master Thief".
[7] After attending the Alternative Press Expo in San Francisco and drinking throughout the day, Wilson left the house of a friend and was found by two passersby, face down and unconscious between parked cars.
[8][9] After a week in intensive care, Wilson was put on an accelerated therapy program, but he still showed major difficulty in summoning words, a common form of aphasia following a trauma of this sort.
After having brain surgery and spending three weeks in rehab, he developed a blood clot in his leg that required another three months in a facility on bed rest, followed by rehabilitation.
Recalling when he first saw Wilson's work (in about 1968) Crumb said, "The content was something like I'd never seen before, anywhere, the level of mayhem, violence, dismemberment, naked women, loose body parts, huge, obscene sex organs, a nightmare vision of hell-on-earth never so graphically illustrated before in the history of art....