In this discussion of Ilene Philipson and D. Bradley Jones’ paper, “Stephen Sondheim: Relational Psychoanalyst of the American Musical Theater,” I contextualize Sondheim’s transformative impact on the Broadway musical and delineate his unparalleled gifts as composer, lyricist and dramatist. I join Philipson and Jones in seeking to explicate the unique potency of his work, offering my own analysis of a Sondheim song using the coauthors’ astute analytic formulations to help uncover why and how it exerts an unusually strong claim on the psyche. I then introduce some of my own interpretations to amplify and complement their arguments, before engaging with their conceit of Sondheim as playing relational analyst to his audience.