In the 1960s Sam Steward began writing and publishing his erotica under the pen name of Phil Andros initially with the Danish magazine Eos/Amigo. Some of his early works described his fascination with rough trade and S/M sex, while others focused on the power dynamics of interracial sexual encounters between men. In 1966, thanks to changes in American publishing laws, he was able to release his story collection $TUD with Guild Press in the United States. By the late 60s, Steward started writing a series of pulp pornographic novels featuring the hustler Phil Andros as narrator. (Steward assumed many other pseudonyms over the years as well, including Phil Sparrow.)
As a leading tattoo artist of the 1950s and 60s, Steward was mentored by master tattooist Amund Dietzel. Steward in turn mentored Cliff Raven and Ed Hardy, encouraging both to practice the Japanese-style tattooing he himself most admired. After retiring from tattooing in 1970, Steward wrote a social history of American tattooing during the 1950s and 60s, which was ultimately published as Bad Boys and Tough Tattoos. Steward abandoned a tenured professor position at Loyala University to pursue a career as a tattoo artist. He eventually became the primary tattoo designer for the Hell’s Angels. Steward also was a lead researcher and subject in Alfred Kinsey’s Institute of Sexuality.
In 2010, a fascinating biography was released on Steward which was written by scholar Justin Spring: Secret Historian: The Life and Times of Samuel Steward—Professor, Tattoo Artist, and Sexual Renegade (Farrar, Straus and Giroux: New York City, 2010). The book was the recipient of many literary honors, and was a finalist for the National Book Award.