During the mid 1960s, record producers and jazz critics coined the phrase Sidewinder Syndrome to describe the funky style of music popularized through the success of Lee Morgan's solo release of "Sidewinder. The funky style, rooted in the heart of the hard bop period (1955-1965), united jazz, Latin influences, and popular black traditions such as gospel and urban blues. Lee Morgan (1938-1973), composer of "Sidewinder," and Richard "Blue" Mitchell (1930-1979) were two prolific trumpet artists from this time period who embraced the Sidewinder Syndrome, and as a result provided a rich improvisational vocabulary, as it pertains to trumpet performance practice. This study presents six annotated transcriptions from each artist focusing on elements of jazz vocabulary and solo construction.The study reveals vocabulary and solo construction preferences within the Sidewinder Syndrome. Results indicated the three most common harmonic generalization elements were digital patterns, change-running, and the bar-line shift. Complex harmonic generalization elements included bebop scale, 3-b9 movement, linear chromaticism, and tri-tone substitution / altered dominant. Vocal inflections derived from gospel music and urban blues were the half-valve, grace note, alternate fingerings, note bending, and fall. Bebop influenced articulation included upbeat-to-downbeat articulation and ghost note. Bebop influenced ornamentation included the two-sixteenth note ornament and the turn. Results suggest solo construction relied heavily upon the sequencing of rhythmic and melodic motives. Space was utilized for clarity, new concepts, and octave displacement. Developmental concepts included running eighth and sixteenth note lines. This study provides an opportunity for students of improvisation to isolate and study jazz vocabulary and solo construction of the Sidewinder Syndrome. / School of Music