BY THE END of 1939, Sinatra was recruited by Tommy Dorsey, “the sentimental gentleman of swing,” who was not necessarily a gentleman but was an exemplary bandleader, demanding and uncompromising. An outstanding soloist on trombone, he recruited such talents as those of trumpeters Bunny Berigan and Ziggy Elman; pianist and songwriter Joe Bushkin; arranger and songwriter Sy Oliver; drummer Buddy Rich; vocalists Jo Stafford, Connie Haines, and Edythe Wright. One of Dorsey’s arrangers, trumpeter Axel Stordahl, achieved greater fame when he left the band to serve as Sinatra’s arranger. A third trombonist hired in the late 1940s, Nelson Riddle, turned out to be the most celebrated of all Sinatra’s arrangers.
Dorsey heard Sinatra on the radio and hired him away from James for his own vastly more successful band. He raised Sinatra’s salary to $125 a week. Sinatra would replace Jack Leonard, a fine crooner (“Marie,” “In the Still of the Night”), who had left the Dorsey band to strike out on his own.
Sinatra hated leaving the James band. The last night was in Buffalo, in January 1940, and Sinatra never forgot it. “The bus pulled out with the rest of the guys after midnight. I’d said goodbye to them all, and it was snowing. I remember there was nobody around, and I stood alone with my suitcase in the snow and watched the taillights of the bus disappear. Then the tears started, and I tried to run after the bus.”
When Sinatra joined Tommy, Jo Stafford, a member of the Pied Pipers, the band’s vocal group, remembers how thin he looked, “almost fragile looking. When he stepped up to the microphone, we all smirked and looked at each other, waiting to see what he could do. The first song he did was ‘Stardust.’ I know it sounds like something out of a B movie, but it’s true: Before he’d sung four bars, we knew. We knew he was going to be a great star.”