[speaking about Billie Holiday]
“What she did was take a song and make it hers,” Sinatra said. “She lived inside the song. It didn’t matter who wrote the words or the music. She made it hers. All the jerks who fucked her and left her. All the nights strung out on junk. All the crackers that treated her like a nigger. They were all in her music. That‘s what she made out of those songs. She made them her story.”
At his best (and he sometimes made choices that were awful, or had them forced upon him) Sinatra did the same. He inhabited a song the way a great actor inhabits a role, often bringing his own life to the music. As a young singer, there wasn’t as much life to draw upon, but it did have a large share of hurts, some because he was Italian American, some because he felt he didn’t have enough formal education, others because of the way he grew up as an only child. Right from the beginning, he had a profound understanding of human loneliness Some of this he must have also drawn from the silent presence of his father, the inconstant exuberance of his mother. Some of it must have been emphasized when he joined the company of the orchestras, living day and night with talented men who had lived other kinds of lives, rich with the presence of family.
– Why Sinatra Matters by Pete Hamill