Glenn Miller's reign as the most popular bandleader in the U.S. came relatively late in his career and was relatively brief, lasting only about three and a half years, from the spring of 1939 to the fall of 1942. But during that period he utterly dominated popular music, and over time he has proven the most enduring figure of the swing era, with reissues of his recordings achieving gold record status 40 years after his death. Miller developed a distinctive sound in which a high-pitched clarinet carried the melody, doubled by a saxophone section playing an octave lower, and he used that sound to produce a series of hits that remain definitive examples of swing music.

One of the prototypical Italian-American crooners, Vic Damone parlayed a smooth, mellow baritone into big-time pop stardom during the '40s and '50s. Early in his career, his inflection and phrasing were clearly indebted to Frank Sinatra, who once famously called him "the best set of pipes in the business." Overall, though, Damone's style was softer than Sinatra's and owed less to the elasticity of jazz, especially since he was a solo performer who never served an apprenticeship with a swing orchestra.