Icons / September 2017

Frank Sinatra: Young At Heart

Before he was Ol’ Blue Eyes, Frank Sinatra sang for pennies, was a keen amateur boxer and carried a lead pipe with him wherever he went. But the potential was always there…

A young Frank Sinatra surrounded by female admirers at a party, circa 1942.

It’s been almost 20 years since he died, and a little over a century since he was born. In between, Frank Sinatra not only defined the singer’s art - his interpretation and phrasing remain the benchmark even today - and established the canon of American standards; he also moulded the idea of modern celebrity - his bewitched ‘bobby soxer’ fan-base made him the original teen idol - and shaped a visual style still resonant over half a century on. But that was Sinatra after success. Before anyone lauded him as The Voice, loved him as Ol’ Blue Eyes, or feared him as The Chairman, he was more a symbol of ethnic achievement, precisely because he had risen from prescriptive Italian-American roots - the son of a Sicilian boilermaker and fireman and a domineering woman who, according to one account of events, had the vision to let Francis Albert drop out of high school to pursue his dream of singing.

That was around 1932. Sinatra worked briefly as a newspaper boy, even for a solitary day as a sports reporter - after his mother insisted he step into the still warm shoes of the man, now deceased, who had until the day before filled that post. Then he started singing in clubs and taverns. By 1939 Sinatra had made his first recording. He’d come a long way quickly, given that his earliest experience of singing was for tips, sometimes playing the ukulele his uncle had given him. That was when he wasn’t dodging fights. A rowdy teenager, Sinatra was also an enthusiastic boxer, a necessary quality growing up in Hoboken, New York, in the inter-war years. He once claimed to carry a lead pipe with him, that he lived, as he put it, “in a plenty tough neighbourhood” - fuelling a childhood rage that would, egged on by alcohol, shape a notorious adult temper that often turned violent and bullying.

But the scar Sinatra bore from the corner of his mouth to his jawline - and which meant he preferred to be photographed from his right - he actually received not in a punch-up but during his birth (he was assumed to be stillborn until a friend of his mother ran his body under the cold tap and he spluttered into life). Other childhood scars were the product of a mastoid operation and severe teenage acne, both of which left his confidence in tatters and his mental state uneasy: Sinatra was a compulsive washer and used Max Factor Pan-Cake to hide what he considered disfigurements.

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Josh Sims

Josh Sims is a writer on menswear, design and much else for the likes of Wallpaper, CNN, Robb Report and The Times. He's the author of several books on menswear, the latest 'The Details', published by Laurence King. He lives in London, has two small children and is permanently exhausted.