This book highlights two series of drawings from the 1950's, where Warhol first explored the controversial and for him deeply personal subject of drag. His oeuvre during the first decade of his career, before he became the godfather of Pop, has proven to be enormously influential on his life's work, yet so far has not received due attention. In 1953, Warhol created two unique series of drawings, quite different from his commissioned work. In one series, he developed an ensemble of spirited women that were derived from photographs of stage divas, and of men in drag. He delved deeper into the art of dressing as the opposite sex with his second series, a set of portraits of men posing in high and low drag. This book considers Warhol's work and its debt to newly discovered photographs that his friend, photographer Otto Fenn, staged explicitly for Warhol's purpose. 'Drag & draw' sheds light on New York's secret gay and drag scenes during the repressive 1950s.