This story of Sinatra begins like this:
Frank Sinatra, the greatest vocalist in the history of American music, elevated popular song to an art. He was a dominant power in the entertainment industries—radio, records, movies, gambling—and a symbol of the Mafia’s reach into American public life. More profoundly than any figure excepting perhaps Elvis Presley, Sinatra changed the style and popular culture of the American Century.
Read the whole thing at The Atlantic while listening to one of his masterpieces below (music, no video):