This performance dissertation consists of a performance component, program notes supporting the performances, annotated bibliography, and a discography. The performances explore five different roles for tenor ranging from the late 18th century to the contemporary period. The purpose of this dissertation is to determine how composers define different characters through various musical and physical characteristics in their compositions. The supporting document examines 18th, 19th, and 20th-century techniques employed by composers to develop characters both musically and theatrically. The first role performed is Luigi in Il tabarro (1918) by Giacomo Puccini (1858-1924) presented November 19-22, 2011. As part of the Art of Argento celebration, the roles of Man with Old Luggage in Postcard From Morocco (1971) and Bentley Drummle in Miss Havisham’s Fire (1996) by Dominick Argento (b.1927) are performed in repertory from April 20-29, 2012. The fourth role is Monostatos in Die Zauberflöte(1791) by Wolfgang Amadeus Mozart (1756-1791) performed November 16-20, 2012. The final role of this project is the title role in Mozart’s Idomeneo (1781) performed April 12-20, 2013. All operas are produced by the Maryland Opera Studio and presented in the Ina and Jack Kay Theatre in the Clarice Smith Performing Arts Center at the University of Maryland, College Park. Archival DVD and CD recordings are available in the University of Maryland library system.