The term piracy marks a slippery category in early modern England: as a legal denomination, it describes the feats of armed robbery at sea for which pirates were prosecuted but their state-sanctioned counterparts, privateers, were not; in a seaman’s professional life, being a pirate was often a phase rather than a stable marker of self-identification. Like their real-life models, literary pirates are contradictory creatures—they shed their pirate identity as quickly as they have adopted it, are used for veiled socio-political commentary, or trimmed to size in order to fit generic constraints. The slipperiness of the pirate has made him (and sometimes her) an attractive figure for early modern playwrights. I argue that John Fletcher and Philip Massinger appropriate the discursive instability of piratical individuals for their pirate plays. Rather than looking at the ideological and political implications of piracy, I analyze the pirate figures in Fletcher and Massinger’s The Double Marriage (1621) and The Sea Voyage (1622) as well as in Massinger’s The Renegado (1623–1624) and The Unnatural Combat (1624–1625) as literary creations. Alternating between the heroic and the villainous, their pirates are convenient plot devices that are attuned to the evolving generic conventions of the early Stuart stage in general and early Stuart tragicomedy in particular.