Frank Sinatra’s secret trick that made him the greatest singer of his age: “Tapped into an experience”
When Frank Sinatra was still just a kid in Hoboken, New Jersey, his go-to guy when it came to singers was ‘The Old Groaner’ Bing Crosby. “But I never wanted to sing like him,” Sinatra said in a 1978 interview with the Boston Globe. “I wanted my own fashion of singing, but I didn’t know what it was going to be.”
Looking back on his formative days, the literally old version of Ol’ Blue Eyes seemed proud of the patience he’d displayed as a young singer, an unpolished gem on the East Coast Big Band circuit of the late 1930s. Rather than trying to achieve some sort of glorious, immature vision for himself as a vocalist, he watched and learned instead, emulating the pros around him for their approach and technique, but always stopping short of outright swiping their styles.
“The idea was to work consistently,” he said, “to sing every night. That’s what gave me a real solid base… To learn, you have to work eight or ten years.” Listening to Rudy Vallee, Sinatra got a better sense of how to scrape off some of his Hoboken accent and phrasings in order to enunciate more clearly. From Billie Holiday, he got an education in bending notes.
Tiny elements were picked up from a dozen other first-rate jazz singers and added to the emerging Sinatra formula. If you believe Frank’s former road manager, Tony Oppedisano, however, one of the biggest breakthroughs in Sinatra’s self-realisation as a singer seemed to come more from a general epiphany about human communication itself.
“Frank and I talked ad infinitum about vocalising and how this talent was all about expressing a complete thought without a break,” Oppedisano wrote in his 2021 memoir Sinatra and Me: In the Wee Small Hours. “He’d tell me, ‘In normal conversation, you don’t run out of air until you’ve completed your thought, even though you don’t know what you’re going to say until a split second before it comes out of your mouth. Why wouldn’t you do the same thing in singing?’”
Oppedisano was several decades younger than Frank and only started working with him in the 1970s, but his recounting of this particular exchange potentially reveals a great deal about how the Chairman of the Board finally figured out how to truly set himself apart from all of his influences.
Sinatra’s goal, according to Oppedisano, was to approach a song’s lyrics like a movie script, convincingly performing the lines each night with a sense of spontaneity, like they were fresh on the page. Since Frank was a pretty good film actor in his spare time, anyway, this wasn’t a great leap to make. “Like he did in his films,” Oppedisano wrote, “he tapped into an experience that he knew would help him lend depth to the lyric.”
Sinatra at least partially seemed to back up this anecdote in his own chat with the Boston Globe in 1978, when he acknowledged that “the songs that I sing and their lyrics are never close to me in my own life, despite what some people think… I try, when I interpret a lyric, to make each person in the audience think he or she is the only person in the world. I try to project to every person individually.”
A more operatic or technically impressive style of singing can certainly connect with people in its own way, but by structuring his performance like a conversation with each audience member, Sinatra did come across as more relatable and magnetically approachable. Like someone you could almost envision getting a whiskey with after the show, even though you logically knew you’d never be cool enough to hang with his crowd.
