The one performance Frank Sinatra only ever wanted to give: “I planned it”
In an alternate world, Frank Sinatra would have pursued his father’s dreams of studying at the Stevens Institute in Hoboken and becoming a civil engineer.
Before he became one of the biggest and most industry-defining names in music history, Sinatra was pushed to prioritise his education while making ends meet by singing occasionally for spare change. Music, for Sinatra, was a casual hobby, something to cut up the monotony of studying for a career that seemed, at the time, far more sustainable in the long term.
Unable to read music and going only by the sounds of those he loved, like Bing Crosby and Gene Austin, Sinatra used music as a way to get by, using the money he gained to buy food or cigarettes. Even as his crossover into the world of music started to take on something more serious, there was still a good amount of luck involved in Sinatra’s journey, with some of his earlier opportunities only appearing because of the persuasion of his mother or sheer happenstance.
With every opportunity, however, Sinatra’s desire to make it grew stronger, and after getting his first taste of commercial success with the Harry James band, it was like a switch went on. Suddenly, Sinatra wanted his name up in lights, and while he was gaining traction, it wasn’t enough. And so, accepting that he wasn’t going to get his break in his current situation, he started planning.
Sinatra was already a big fan of Tommy Dorsey before joining his lineup. At this particular juncture, however, he had his eyes on the prize, knowing that one chance was all he needed to make it work. As he recalled in 1975, “Only once in my life I saw something that might happen, and I had tried to plan it, and that was to sing as a vocalist with the Tommy Dorsey Orchestra. That was an objective, I wanted to do that because, after watching all of those orchestras who were equally as marvellous, in those days, one band was as good as the other, there were different styles, and they had fine singers.”
He went on, “But I used to go and buy a ticket [to Tommy Dorsey] and watch the band and watch how he handled the singers, and they were handled with such finesse and showcased. It wasn’t a matter of an introduction, vocal chorus, orchestra, and out. He would set a singer up so the singer would sing the first chorus, the orchestra would play a small piece of music, and the singer would finish it. In other words, he was featured.”
Sinatra also elaborated on the different techniques that he became endeared to, like Dorsey’s breath control, which he studied for years and still couldn’t figure out his “secret”. However, he also became mesmerised by the way Dorsey approached vocals like a trombone, which gave the entire dynamic a much smoother and softer feel, and something uniquely fresh that didn’t exist in other orchestras.
A lot of Sinatra’s mannerisms can be traced back to Dorsey. Alongside becoming a mentor for the singer, Dorsey also encouraged Sinatra to become a perfectionist and constantly look for new ways to improve his own performance, whether in the subtleties of breath control or a broader mindset towards telling a story on stage.
Sinatra also used him as a building block to shape his own distinctive style, much like he did with many of his other influences. For instance, in Sinatra’s world, it was never about simple imitation, but blending all of his favourite traits into one, all while making the audience feel as though what they were experiencing was hand-crafted for them only. It was pure magic, nurtured from sheer observation.
