This dissertation explores the themes of collaboration and creativity in the relationship between arranger Nelson Riddle and vocalists Frank Sinatra and Ella Fitzgerald. It examines the balance between structure and freedom as well as the specific musical results that emerge from collaboration between an arranger and vocalists who are considered among the greatest in their fields. An examination of their interactions, musical scores, and performances, reveals that the constraints that are present in a collaborative effort can lead the artists to find a shared process to make a creative, unified product.

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