This chapter considers the role of gender as it is embodied in late nineteenth- and early twentieth-century butter sculpture. Caroline Brooks used butter as a means to circumvent nineteenth-century restrictions on women’s career mobility. Brooks emerges as a feminist role model who helped inspire other women to pursue their dreams, even while appeasing period gender expectations. On the other hand, four butter portraits of Theodore Roosevelt offer an opportunity to examine ideas about the nature of masculinity. The chapter discusses that the butter portraits illustrate the high points of Roosevelt’s career and also suggests a political and gendered context for both the period and the art.