A fundamental task in empirical aesthetics is to determine why some artistic creations earn the label “masterpiece” whereas others slip into oblivion. Computer content analyses can help us achieve this goal, first, by isolating connections between the differential aesthetic success of diverse works and their content attributes, and, second, by identifying the compositional, biographical, and historical correlates of those content analytical predictors. After reviewing the key findings with respect to the thousands of musical pieces defining the classical repertoire, this investigation strategy is applied to 105 compositions (containing 593 themes) by Beethoven. Two distinct measures of artistic impact, compositional popularity and aesthetic significance, were shown to be associated—often in a curvilinear fashion—with four content characteristics: melodic originality and variation and metric originality and variation. Some of these attributes are linked to such circumstances as the work's key, the instrumentation, and the number of movements, Beethoven's age and concurrent level of productivity, stress, and health, and the presence of international war in Europe. Hence, an objective, computer analysis can enhance our understanding of the aesthetic and creative processes behind a single creator's artistic reputation.