
Tommy Dorsey: The man who made Frank Sinatra possible
If Frank Sinatra saying “The only two people I’ve ever been afraid of are my mother and Tommy Dorsey” doesn’t tell you everything, then I don’t know what will.
Yet equally, when you think of Sinatra even casually, there’s only one image that pops up. The Chairman of the Board. Definitive. Singular. There was very rarely anyone else who was ever sharing his spotlight. The concept of the man being anything else but a lone wolf seems at odds with everything we know.
But Dorsey was different. On one hand, yes – he was an inimitable figure who could easily put people in line when he needed to. However, underneath that veneer was someone who essentially became like a second father to ‘Ol’ Blue Eyes’, showing him the ropes of the industry he would go on to single-handedly master, while also being the closest of confidants.
It was back in the early days – the late 1930s, to be exact, a good few years before the notion of Sinatra-mania ever crossed anyone’s mind – that the young future star knew he was destined for greater things, and was becoming frustrated by the inhibition of his role as the singer in the Harry James Band.
Without knowing it at the time, jumping ship to Dorsey’s group would be the move that definitively changed the course of his life forever. Under the wing of the trombonist and bandleader, Sinatra quite simply blossomed from the very first second he set foot on stage with the outfit in Rockford, Illinois, on January 26th, 1940.
“You could almost feel the excitement coming up out of the crowds when the kid stood up to sing,” Dorsey recalled of his first performance, where he opened with the tune ‘Stardust’. “Remember, he was no matinée idol. He was just a skinny kid with big ears. I used to stand there so amazed I’d almost forget to take my own solos.”
But indeed, that same “skinny kid with big ears” would go on to achieve things that people could never imagine, no matter how captivating his raw talent may have been. That didn’t come without its growing pains – as Sinatra’s status became bigger, he was well-accustomed to recording with Dorsey but eventually wanted to go it alone, resulting in a major battle of wills.
It was not just his adopted paternal role that was at stake for Dorsey. Under the contract he had agreed with the band, he also had a 43% cut in Sinatra’s lifetime earnings, which, for better or worse, he wanted his money out of. When the legal battle ended, and the Chairman emerged victorious, the father figure reportedly told him, “I hope you fall on your ass”.
No one ever knew whether he was quite serious or not. Nevertheless, Sinatra’s relationship with Dorsey was one that could never be broken, no matter how much they tried – at the end of the day, whose showmanship, mannerisms, and style did the entertainer learn his every move from, and who, ultimately, did he owe his career to… I think we all know the answer to that.


