WHEN IN A ROOM OF ONE’S OWN VIRGINIA WOOLF ASKS, “WHAT if Shakespeare had a sister?” Woolf reaches back through layers of cultural history to locate reasons why so little literary work by women has come down through the centuries. That imaginary sister, Judith, was as equally talented and ambitious as her brother, but when she reached London, she met only scorn and rejection. To help Woolf understand the particular “maleness” of the English literary heritage, she concluded that for centuries, artistic ambition in a woman was considered not only out of place and purposeless, but it was also regarded as utterly contemptuous of the dominant society. In this investigation of women in solo comedy performance in America, it becomes evident that Woolf’s observations about women’s ambition also apply to women in comedy. Women’s comedic ambition has met with considerable resistance, particularly in Phyllis Diller’s early days in the ’50s and ’60s. Despite the presence of a growing number of famous female stand-ups, many contemporary stand-ups assert that men’s stand-up commands more respect than women’s (Wisecracks). Because of this cultural resistance to women’s comedy, I have argued for the significance of comedians like Lily Tomlin and Roseanne, who have by their skill and style expanded the field for women.