Billie Holiday, born 100 years ago today, may not have been as tenaciously devoted to craft & technique, but she can blow your head off. It's the old dilemma: technique or passion—but great artists, like great lovers, have both.
Sinatra's mean attitude toward women is what comes out to me in his singing. Johnny says all singers learned from him—if you can understand Johnny Cash's words, it's because he understood Sinatra's phrasing.
Billie Holiday just seems beyond understanding.
Not so much comparing, just thinking about why I hands down prefer Holiday.
Also see: Frank O'Hara's fantastic poem "The Day Lady Died." Is there a great, moving poem about Sinatra?