Sam Doyle lived in a home he built for his family on ancestral farmland on St. Helena Island, South Carolina, where Penn School was established in 1862 to assist freed slaves. He learned the importance of Gullah culture from elders and the value of history at Penn. Though his childhood artworks were admired, he didn't consider himself an artist until his senior years. The scholar and collector Gordon W. Bailey notes, "Doyle placed his first painting in his yard in 1944 and thereafter added others. Following his retirement in the late 1960s, he committed to 'painting history.' He blended Gullah lore and his Baptist faith into a rich multicultural impasto. Two series, 'Penn' (school) and 'First' (achievement or event), commingled with folkloric works and established Doyle's mission. His museum-like display evolved into the St. Helena Out Door Art Gallery." Doyle curated an oeuvre of robust paintings including luminaries—such as Dr. Crow, Mr. Fool and Ramblin' Rose—and African American celebrities such as Ray Charles, Joe Lewis and Jackie Robinson. Corcoran Gallery of Art curator Jane Livingston selected Doyle's work for the 1982 traveling exhibition Black Folk Art in America: 1930–1980. The exhibition introduced Doyle to a wide audience including the artists Jean-Michel Basquiat, who collected his works, and Ed Ruscha, who has cited Doyle's influence and painted a posthumous tribute titled Where Are You Going, Man? (For Sam Doyle), 1985. As Bailey observed, "The artist summed up momentous events with poetic simplicity and had a genius for distilling the essence of personality."

Valérie Rousseau, “Rocking Mary/Mr. Fool,” exhibition label for Self-Taught Genius: Treasures from the American Folk Art Museum. Stacy C. Hollander and Valérie Rousseau, curators. New York: American Folk Art Museum, 2014.