[6][1] He competed as a wrestler in high school, during which time he described becoming "totally fixated on men with big pecs and fine nipples," which became lasting inspirations for his art.

[1] Shapiro created Harry Chess in response to a 1964 ad in the New York Times by Clark Polak seeking "a cartoonist for a new gay and sophisticated magazine" called Drum.

[1] In 1977, Drummer co-founder John Embry hired Shapiro and Fritscher to be the magazine's art director and editor-in-chief and tasked them with moving the publication from Los Angeles to San Francisco.

[2] Numerous gay bars and clubs featured Shapiro's artwork in promotional materials, including Caldron,[9][10] The Eagle,[11] and The Slot.

[15] In his 2006 autobiography, Fritscher wrote:[2]If there is a gay Mount Rushmore of four great pioneer pop artists, the faces would be Chuck Arnett, Etienne, A. Jay, and Tom of Finland.The Leather Archives & Museum in Chicago holds some of Shapiro's art.