Early on his vocal talent was modest, and nobody knew it more than Sinatra. He learned not only from his idol, Bing, but from jazz singers like Billie Holiday, whose emotive style spoke to a troubled loner. Mr. Kaplan details just how hard Sinatra worked at his craft, including a lifelong obsession with phrasing and most of all, song lyrics. “Feeling the words, and remembering how Billie could tell you her whole life story in the glide of a note,” Mr. Kaplan writes, “Frank began to sing the lyrics as if he really meant them, and something happened.”
It was as the vocalist for Harry James’s big band that Sinatra first made his name, and, if James had had his way, it would have been as Frankie Satin. “You want the singer, take the name,” Sinatra told James. In an era when Anglo-sounding stage names were simply part of showbiz, it was no small thing for Sinatra to take a stand; Tony Bennett and Dean Martin ditched their Italian surnames years after Frank fought for his.
The stint with trombonist and bandleader Tommy Dorsey put Sinatra in the national spotlight. As Mr. Kaplan shows, Dorsey is a crucial mentor—Frank copies everything from his on-stage breath-control technique with his horn to his cologne. He was a towering figure who ruled his orchestra with an iron hand. The only two people he was ever afraid of, Sinatra once said, were his mother and Tommy Dorsey.