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Vail Jazz column: Was Sinatra a jazz singer?

Howard Stone
Special to the Daily |

On July 13, Vail Jazz celebrates the centennial of the birth of Francis Albert Sinatra in a special show entitled “A Swingin’ Affair,” featuring Curtis Stigers and the H2 Big Band. Sinatra, variously known as “The Voice,” “Ol’ Blue Eyes,” “The Chairman of the Board,” “Frankie” and “The Sultan of Swoon,” was by most accounts the greatest entertainer in the history of American pop culture, with a career that spanned more than five decades from the late 1930s to the 1990s. Dropping out of high school with no formal music training, he couldn’t read music, but he went from a teen idol to a living legend. His first hit, “All or Nothing at All,” foretold his future and summed up his philosophy and the arc of his career.

Much has been written about him as a cultural icon and the public has had an insatiable appetite for the salacious details of his personal life and all his exploits, womanizing, connections to the mob, leader of the Rat Pack and much more. It should not be forgotten that he was the winner of nine Grammy Awards, three Academy Awards, a Presidential Medal of Freedom and a Congressional Gold Medal. In addition, he spoke out against anti-Semitism and was involved in the civil rights movement as well as being very philanthropic.

Defining jazz



Sinatra was no doubt a great pop singer, but I focus here on a simple question: Was he a jazz singer? I’ll answer that with another question: Does it snow in Vail? The unequivocal answer is YES!

Dropping out of high school with no formal music training, he couldn’t read music, but he went from a teen idol to a living legend.

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So what is a “jazz singer”? While there is no rigid definition, the hallmark of jazz and therefore a jazz vocalist is to swing and improvise. Swing is hard to define, but according to jazzinamerica.org, a performance swings when it uses “a rhythmically coordinated way … to command a visceral response from the listener (to cause feet to tap and heads to nod).” If you still don’t get what swing is, listen to “I’ve Got You Under My Skin” from “Songs for Swingin’ Lovers,” one of Sinatra’s greatest recorded tunes. If you still don’t get it, I suggest that you focus your listening on polka music!



To improvise in the world of jazz is to compose on the spot. Techniques such as singing behind the beat, accenting words and changing the phrasing (grouping lyrics in a way that is different than the composer wrote them, but suits the vocalist’s sensibility of how the lyrics should be interpreted), altering (and substituting) lyrics, all allow a vocalist to make a song his own. In essence, by using these techniques (not just as techniques, but as a way of communicating with the listener), the vocalist becomes the composer of a new song (based of course on the original one) and if the vocalist can make the listener tap his feet, click his figures or nod his head, you have a jazz vocalist.

Sinatra had swagger, and his half-cocked hat said that he was a jazz musician, but attitude and attire are not enough. He sang and recorded with many jazz greats. His phrasing and music sensibility were admired by great jazz musicians such as Count Basie, Miles Davis and Lester “Prez” Young and many more, but it is not the company you keep or the admirers that you have, but how you sing that determines your bon fides as a jazz singer. He recorded albums with the great Nelson Riddle with titles such as “Swing Easy,” “Songs for Swingin’ Lovers” and “A Swingin’ Affair,” but branding is one thing and really swinging is another.

An ‘honest’ singer

Ultimately, you have to be able to deliver the goods and The Chairman of the Board could. Learning early in his career how to sustain long unbroken phrases without pausing to catch his breath allowed him to be adventurous with the phrases of a song. Sinatra listened to the jazz instrumental soloists he admired and used similar phrasing in his performances. Students of Sinatra’s catalog can point to numerous renditions of Cole Porter and Johnny Mercer lyrics that Sinatra “tweaked,” remaking these standards into his own. His diction was impeccable but yet had a conversational quality. It has been said that he had an incredible sense of time which allowed him to alter a phrase so the beat didn’t always coincide with the ending of a rhyme, but created a sense of sincerity making the lyrics more personal and causing the listener to believe the story that was being told. In fact he was quoted as saying: “When I sing, I believe. I’m honest.”

Howard Stone is the founder and artistic director of The Vail Jazz Foundation, which produces the annual Vail Jazz Festival. Celebrating its 21st year, the Vail Jazz Festival is a summer-long celebration of jazz music, culminating with the Labor Day weekend Vail Jazz Party. For tickets or to learn more about Vail Jazz’s 100th birthday celebration of Frank Sinatra on July 13, visit vailjazz.org.


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