Few entertainers have shaped American culture as indelibly as Frank Sinatra. Rising to fame in the 1940s as a crooner with the Harry James and Tommy Dorsey orchestras, Sinatra quickly became a solo sensation, his smooth baritone and intimate phrasing redefining popular music for a generation of listeners. By the 1950s and ’60s, he had cemented his place not only as a recording artist—with now clas...