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 classics like “New York, New York” and “My Way”—but also as a film star, earning an Academy Award for From Here to Eternity and anchoring the Rat Pack’s orbit of glamour in Las Vegas and Hollywood, alongside fellow crooners including Dean Martin and Sammy Davis Jr. A consummate entertainer who thrived in the company of others, Sinatra lived in residences that mirrored the many facets of his life: places of retreat, rehearsal, and revelry in equal measure.…