Andy Warhol left Pennsylvania for New York in 1949 to become a commercial illustrator. Upon arriving in New York, he quickly realized that photography was putting many commercial illustrators out of business. (Nina Schleif, Drag and Draw at page 11.) Warhol adapted to this reality by incorporating photography into many of his works; in the 1950s, he would photograph his subjects and then trace over the photos, incorporating his own techniques and whimsical additions into the drawings. (Id.) His interest in photography was intensified by his encounters and later friendship with Otto Fenn; the two met in 1951 and Warhol became a regular at Fenn’s photography studio, which is said to have attracted gay creative minds of New York in the 40s and 50s. Warhol helped Fenn with the backdrops for his photography shoots; Fenn’s photographs – often of men in drag – became the foundations for many of Warhol’s early drawings.

Warhol integrated the drawings gleaned from his photographs throughout his work – both in and after the 1950s. Some were given to friends as gifts; others appear in the books Warhol created in the 1950s. Among these books is Ladies’ Alphabet, which was unpublished; it was written presumably alongside A is an Alphabet, the latter of which was published in 1953. Ladies’ Alphabet features Warhol’s drawings presumably alongside the prose of his constant collaborator Ralph Thomas “Corkie” Ward. This book, according to Patrick Smith of the Andy Warhol Museum, is a “very sophisticated jest that was carefully planned and impresses us on first sight as carefully unplanned.” (Schleif, Drag and Draw at page 66.) The book is on its face whimsical, but “explored the seriousness of gender, identity, and feelings of abandonment and attraction.” (Mulroney, Andy Warhol: Publisher at page 11.)

Many of the subjects depicted in this book are based on photographs of famous actresses (that Warhol likely found in magazines), or of photographs that he and Otto Fenn took of men in drag. (Nina Schleif, Drag and Draw at page 50 and page 8.) This drawing resembles those drawings created for Ladies’ Alphabet, and the drawings that followed throughout the 1950s.