This dissertation raises problems with the methodology of Schenkerian analysis and attempts to find solutions. Balancing ideological critique, intellectual history, and musical analysis with criticisms of the theory itself, my aim is to argue that Schenker’s conception of his own theory—and in particular of his background Urlinie—has greatly restricted the analytical possibilities of his methodology, including how it is practiced today. Chapter 1 will introduce and summarize this argument as a whole, including some of my musical and philosophical priors. Chapter 2 will explore how Schenker’s assumptions about his theory fulfill what I will (following Nicholas Cook) characterize as a “retrospective prophecy,” which I argue is continuous with the motivated and circular reasoning that propped up Schenker’s problematic wider ideology. Chapter 3 introduces two ideas that combat this tendency and inform my own analyses: the “modified” approaches to Schenker (in the work of scholars like David Neumeyer) as well as “oscillation” between different analytical interpretations (as Marianne Kielian-Gilbert describes work like Joseph Dubiel’s). Chapter 4 attempts to bring these two together, and I argue that this opens the way to a greater degree of analytical possibility than has hitherto been realized. In short, I argue that contemporary Schenkerian analysis has remained too tied to Schenker’s original formulation, to the detriment of the theory, but that not many Schenkerians have appreciated this. Along with attempting to find solutions to my problems, then, I want to convince Schenkerians that there are problems here to be solved in the first place, by showing how the very things analysts find valuable about the theory can be improved through the incorporation of “modified” and/or “oscillatory” approaches.