The parade of sexualized personae that features in this chapter's title carries a history. Libertines, rakes, and dandies are figures that occur in a sequence that begins in the sixteenth century and effectively comes to an end by the twentieth century, although it is a sequence marked by overlaps and ambiguities. Drawing on a rich body of scholarship, the chapter traces passages from the libertine through the rake and dandy, concentrating on each in turn. It focuses on metropolitan England, where, arguably, the libertine, the rake, and the dandy came most vividly to life. Libertinage has a long and complex history that reaches back into antiquity. In the fifteenth and sixteenth centuries, the category was mainly applied to a kind of writing that already held a firm place in manuscript culture. Rake is more concretely bound to particular sites and institutions than the libertine, and especially to a particular moment in the court's recent past.