Andy Warhol (1928-1987) and Robert Mapplethorpe (1946-1989) are well known for significant work in portraiture and self-portraiture that challenged gender roles and notions of femininity, masculinity, and androgyny. This exciting and original book is the first to consider the two artists together, examining the powerful portraits they created during the vibrant and tumultuous era bookended by the Stonewall riots and the AIDS crisis. Several important bodies of work are featured, including Warhol's 'Ladies and Gentlemen' series of drag queen portraits and Mapplethorpe's photographs of Patti Smith and of female body builder Lisa Lyon. These are explored alongside numerous other paintings, photographs, and films that demonstrate the artists' engagement with gender, identity, beauty, performance, and sexuality, including their own self-portraits and portraits of one another. Essays trace the convergences and divergences of Warhol and Mapplethorpe's work, and examine the historical context of the artists' projects as well as their lasting impact on contemporary art and queer culture. Firsthand accounts by the artists' collaborators and subjects reveal details into the making and exhibition of some of the works presented here. With an illustrated timeline highlighting key moments in the artists' careers, and more than 90 color plates of their arresting pictures, this book provides a fascinating study of two of the most compelling figures in 20th-century art.