Tom Stoppard is primarily concerned with absurdism, metatheatricality, and language as tools to explore the nature and various definitions of reality. Rosencrantz and Guildenstern are Dead, Stoppard’s first major work, focuses on all of these questions—and is specifically one of Stoppard’s most theatrical plays. Doubling is a longstanding theatrical tradition in which one actor portrays multiple characters within a dramatic work. Over the past century, various directors have rediscovered ways to use doubling in more conceptual ways, making daring implications about politics, sexuality, the purpose of theatre, and offering alternate interpretations to classical works. Rosencrantz and Guildenstern are Dead is a work that traditionally “requires” anywhere from fifteen to thirty-five actors, yet its metatheatrical implications could be greatly strengthened by the use of doubling. For that reason, this thesis, in conjunction with the process of directing a production of Rosencrantz and Guildenstern are Dead, examined how Stoppard’s first masterpiece can be thematically strengthened by the use of doubling.