This chapter explores Leonard Bernstein’s work as pianist-conductor, including early influences that shaped Bernstein’s choice to conduct while playing, preferred repertoire (Mozart, Beethoven, Ravel and Gershwin), and reception by audience, and critics. Bernstein’s technique as conductor-pianist is analysed through audio and video recordings, as well as through the study of Bernstein’s annotated scores from the New York Philharmonic Archives. A brief history of conducting from the piano serves to contextualize this notable aspect of Bernstein’s career. Particular attention is given to Gershwin’s Rhapsody in Blue, which was among Bernstein’s most frequently performed pieces while leading the orchestra from the piano. An analysis of three different recorded performances of Bernstein’s performance of the Rhapsody – two audio recordings and one televised broadcast – provide insight into significant moments (and challenges) for Bernstein as pianist-conductor, as well as key interpretive changes in his performance over time.