In 1939, Frank Sinatra scored his very first success, "All Or Nothing At All," with trumpeter Harry James' Orchestra. The following year the young singer began an extraordinary two year apprenticeship with the much classier Tommy Dorsey Orchestra, a regimen which taught him everything he needed to know about musical taste and judgement if not popular adulation. Make no mistake, however; from the beginning, through sheer dint of will, Sinatra managed to make his time with the master trombonist and bandleader a collaboration of musical equals.
Milestone recordings like "Stardust," "I'll Be Seeing You," "I'll Never Smile Again," "Everything Happens To Me" et al are both big band classics and the beginning of a new age of romantic popular singing. No male singer had ever gone as far as Sinatra did in exploring the tender feelings expressed in these songs, in identifying so completely with a given song's meaning. It was a revolution in popular sensibility that we are still living through several decades later.