In this paper I examine the efficacy of Schenkerian analysis on jazz music, primarily in the scholarship of the late music theorist Steve Larson, through a variety of music theoretical and philosophical frameworks. While my understanding of Schenkerian theory is rooted in basic models, the purpose of this paper is to address the issues in the application of the theory as they may be understood by practicing jazz musicians and scholars alike. My work draws from various experts in adapting Schenkerian theory for use in jazz music and from the philosophical and analytical frameworks of David Lewin and George Lewis. The key questions guiding my evaluation of the efficacy of Larson’s specific methodology are : (1) how do Larson’s models hold up to scrutiny as analytical tools transplanted from one distinct idiom into another and how might they compare to other models present in jazz theory discourse,(2) what are the philosophical claims, both explicit and implicit in Larson’s scholarship on the process and intent of improvisers, and (3) what aspects of Larson’s approach are left unexplored, including historical, cultural, pedagogical, and idiomatic considerations? My interest in this study stems from the philosophical ramifications of Larson’s writing and his claims concerning improvisation as well as my own reflections on teaching jazz theory in higher education, which in turn have informed my performance practice and scholarly identity within the greater discourse of the jazz and improvised music community.