This chapter considers popular music icon Frank Sinatra’s fifty years singing “Ol’ Man River.” He first sang the song in the early 1940s, when it was an unlikely addition to his repertoire of love ballads. In these years, “Ol’ Man River” functioned as a showpiece for Sinatra’s voice and a display of masculinity: some listeners didn’t think the tune worked for a crooner but Sinatra kept on singing it. Across his career, he framed the song as a “classic” or “great” piece of popular art. Sinatra took two approaches to “Ol’ Man River,” which can be characterized as the bombastic and the intimate. Central to both was a choice of phrasing that pulls the listener’s attention toward Sinatra’s technical ability to sustain a long musical line on a single breath. This idiosyncratic approach to the tune hints that Sinatra conceived of “Ol’ Man River” primarily as an opportunity for vocal display.
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