Much of guitarist Wes Montgomery’s study of jazz improvisation came from imitating Charlie Christian’s guitar solos. The purpose of this study is to identify and examine significant improvisational traits that Wes Montgomery developed as a direct result of his imitation and assimilation of Charlie Christian. The dissertation investigates the musical traditions in Christian’s playing that were absorbed into Montgomery’s playing and how Montgomery was able to use these traits to foster new musical traditions. The solo transcriptions are limited to Montgomery’s early recordings between 1957 and ending with his 1960 album The Incredible Jazz Guitar of Wes Montgomery. The study also examines the relationship imitation has with creativity in jazz and how originality is influenced by the past. The dissertation examines the two guitarists’ use of five harmonic and melodic devices over dominant harmonies: scales, arpeggios, use of chromatic pitches, formulas and enclosures, and harmonic substitutions. The study focuses on how Montgomery’s melodic and harmonic treatment of dominant harmonies has been influenced by his imitation and assimilation of Christian’s improvisations. The study examines how Montgomery differentiated himself in his improvisations from Christian’s. A strong emphasis is given to the significance of these differences and how these differences are connected to Montgomery’s originality and innovation. This dissertation confirms that Montgomery’s innovation was strongly linked to his imitation of Charlie Christian. It also suggests that devotion to the imitation of past artists is needed in developing an original voice in jazz. / Biographical history and musical development of Charlie Christian -- Biographical history and musical development of Wes Montgomery -- Stylistic traits of Charlie Christian over dominant-seventh harmonies -- Stylistic traits of Wes Montgomery influenced by Charlie Christian -- Conclusion. / School of Music