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This article analyzes four musical works written for the commemorative centennial year of the Emancipation Proclamation, 1963: We Insist! Max Roach’s Freedom Now Suite, featuring the vocalist Abbey Lincoln; Duke Ellington’s theatrical production My People; John Coltrane’s “Alabama”; and Nina Simone’s “Mississippi Goddam.” This diverse set of songs expresses the contradiction of Black life and death in America during the modern civil rights movement. Within the structure of each musical piece is a tension described as “the break” in which resistance to the disavowal of Black suffering and the demand for true freedom is performed. The analysis of such breaks helps explain the tenuous position of Black performers in this moment, the precipice they navigated onstage in 1963, as well as a larger tension that undergirded the Black freedom struggle: namely, the impulse to celebrate liberation against a cognizance of its failure to materialize in any substantive form.