Clause 12 of the production contract for Anthony Davis’s 1986 opera, X: The Life and Times of Malcolm X, reads: “The word ‘jazz’ should not be used in any connection with this piece, including Anthony Davis’s biography.” Although vehemently opposing the classification of his work as jazz, Davis simultaneously sought to position the “jazz tradition” as the central impetus for the creation of that perennially elusive form: “American opera.” To comprehend this apparent contradiction, this talk traces intersections between jazz and opera through three case studies. The first considers the unperformed Wagnerian “jazz opera” American Romance (1924-1929) by H. Lawrence Freeman, founder of the Harlem-based Negro Grand Opera Company. The second concerns Sam Rivers and the Harlem Opera Society’s Black Arts Movement-inspired “jazz improvisational operas” of the 1960s and 1970s. The final case study returns to Anthony Davis’s X. Building on the earlier analyses, Gutkin reformulates the problem of “jazz” in the work—and interpret its racial significance—in terms of a longstanding ambiguity in opera concerning the representation of music within an already musical form.