Frank Sinatra, says the critic Robert Christgau, was the greatest American singer of the twentieth century, for in every phrase his blend of Hoboken street swagger and colloquial ease “turned English into American and American into music.” A teen idol in his twenties, a critical success in his thirties, he was by age fifty an icon, synonymous with the dark glamour of late-night jazz clubs and the criminal underworld that controlled them. When Lauren Bacall told Humphrey Bogart and his friends that they looked like a “rat pack,” an elite, legendary circle of friendship was born, with Sinatra as its central figure: suave but tough, a master of breath control and the common touch. He had a defensive, defiant pride in his Italian heritage and often dodged allegations of Mafia support. The cultural hero of the Greatest Generation, Sinatra was and is beloved by singers and musicians the world over, from Antonio Carlos Jobim to Miles Davis, from Bruce Springsteen to Bono.