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This dissertation presents a comparative analysis of four influential pianists from the early eras of jazz piano performance: Ferdinand “Jelly Roll” Morton, James P. Johnson, Earl Hines, and Art Tatum. Through detailed examination of representative recordings from 1921-1940, and over 200 musical examples, this study traces foundational stylistic developments in solo jazz piano during what is widely recognized as the genre's golden age.Despite solo jazz piano's vital role in jazz performance, it has received relatively little comprehensive scholarly attention compared to ensemble jazz. This research addresses that gap by analyzing the harmonic, rhythmic, and pianistic characteristics demonstrated in twenty selected recordings spanning nearly two decades. The study examines both shared techniques among these pianists and their distinctive individual approaches, tracking how their styles developed throughout the period and identifying elements that remain audible in contemporary jazz piano performance. Using transcription-based analysis supported by historical and biographical context, this research documents the transition from ragtime-influenced styles toward increasingly complex harmonic and rhythmic approaches. The comparative methodology reveals how these pianists developed distinct solutions to the unique constraints and possibilities of solo performance while collectively establishing fundamental techniques that would influence subsequent generations. Findings include a clear trajectory from the largely diatonic harmonic vocabulary and syncopated eighth-note rhythmic patterns of early recordings toward the chromatic harmony and varied rhythmic approaches evident in later performances, particularly those of Hines and Tatum. The analysis traces technical innovations including the development of tritone substitution, polyrhythmic syncopation patterns, and pianistic techniques informed by other instruments and genres. This study contributes to jazz scholarship by providing a broad comparative analysis of solo jazz piano from this crucial period. The research offers new perspectives on individual pianists’ contributions while illuminating broader patterns of stylistic development that shaped jazz piano's development. These findings have implications for jazz pedagogy, performance practice, and our understanding of how solo traditions influenced the broader trajectory of jazz as an art form.