This paper contains a historical, theoretical, hermeneutical, and performative analysis of several song cycles, songs, and an aria. Chapter One contains an analysis of the historical, theoretical, and social elements of the song cycle, Try Me, Good King: The Last Words of the Wives of Henry VIII, by Libby Larsen, elements which have led to its continued success and popularity. Chapter Two contains a hermeneutic analysis of harmonic and melodic aspects in the two songs, “Pantomime” and “Pierrot” in Quatre chansons de jeunesse by Debussy. These elements portray several commedia dell’arte characters through rhythmic figures, motives, and harmonic structure. Chapter Three contains a comparison of the personal lives of Robert Schumann and Friedrich Rückert, and Hugo Wolf and Eduard Mörike. The individual experiences and artistry of these composers are combined in the songs, “Auf ein altes Bild,” (Wolf) and “Jasminenstrauch” (Schumann). Chapter Four contains a discussion of traditional and non-traditional opera staging of the opera L’elisir d’amore, and how staging directions may affect the performer’s artistic choices and audience appeal. These works were performed in partial fulfillment of the requirements for the Master of Music degree on March 20, 2020 in The University of Texas at San Antonio Recital Hall.