Much information concerning the trajectory of the New Woman in American society can be gathered by studying paintings of theatrical scenes centered on female performers in New York City from the years of the Victorian era through the decade of the Great Depression. This dissertation concentrates primarily on the work of male artists whose canvases recorded not only the evolution of popular entertainment, but also revelatory transformations in the status of women in society during those years. This study begins with two of the leading proponents of American realism, Thomas Eakins and Robert Henri, and continues with four artists they influenced: Everett Shinn, Walt Kuhn, Reginald Marsh, and Edward Hopper. Their work also reflects their own reactions to America's changing cultural environment as gender barriers collapsed and women gained more power and determination over their own lives. These images of actresses, singers, and showgirls provide clues to the continuing momentum of women's accomplishments as they overcame the impediments of economic hardship and traditional chauvinistic values concerning women in general, and in particular, against women who seemingly debased themselves by performing onstage.