Frank Sinatra’s Effect on Jazz Music: Inside the Vail Jazz Festival


Frank Sinatra is one of today’s most revered musicians, winning countless awards for his music and known to have forever changed American popular music.
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Frank Sinatra was, by most accounts, the greatest artist in the history of American pop culture. His career spanned more than five decades, from the late 1930s to the 1990s. Dropping out of high school without formal musical training, he could not read music, but he went from teenage idol to living legend. His first hit, All or Nothing at All, predicted his future and summarized his philosophy and the arc of his career.

Sinatra was a complex man. He has won nine Grammy Awards, three Oscars, a Presidential Medal of Freedom and a Congressional Gold Medal. He spoke out against anti-Semitism and was involved in the civil rights movement while being very philanthropic. There was his ‘bad boy’ side too, but I’m focusing here on a simple question: was he a jazz singer? I will answer this question with another question: is it snowing in Vail? The unequivocal answer is: yes.

Not just a pop singer

The hallmark of jazz and therefore of a jazz singer is to swing and improvise. In “Jazz in America” ​​it is said that a performance oscillates when it uses “a rhythmically coordinated manner … If you still don’t understand what swing is, listen to” I’ve Got You Under My Skin “by One of Sinatra’s best recorded tracks, “Songs for Swingin ‘Lovers.” If you still don’t understand, I suggest you focus your listening on the polka.

To improvise in jazz is to compose on the spot. Techniques such as singing behind the beat, emphasizing words, and changing the phrasing (grouping lyrics in a way different from that written by the composer, but tailored to the singer’s sensitivity as to how the lyrics are to be interpreted) , changing and replacing lyrics all allow a singer to make a song their own. Essentially, using these techniques, the singer becomes the songwriter of a new song and if the singer can stomp the listener’s foot, click their numbers, or nod, you’ve got a jazz singer.

Sinatra’s swagger and half-bicorn hat said he was a jazz musician, but attitude and attire are not enough. He has sung and recorded with many jazz greats, admired by musicians such as Count Basie, Miles Davis and Lester “Prez” Young. But it’s not the company you keep or the admirers you have, but the way you sing that determines your good faith as a jazz singer. He recorded “Swing Easy”, “Songs for Swingin ‘Lovers” and “A Swingin’ Affair”, but branding is one thing and swing is another.

At the end of the day, you have to be able to deliver the goods and “the chairman of the board” could. Learning early in his career to sustain long, unbroken sentences without stopping to catch his breath allowed him to be adventurous with the lines of a song. Sinatra admired many jazz instrumental soloists and used similar phrasing in her performances. His diction was impeccable but still had a conversational quality. He had an incredible sense of timing. This allowed her to alter a phrase so that the beat didn’t always coincide with the end of a rhyme, but created a sense of sincerity making the lyrics more personal and making the listener believe the story 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 Vail Jazz, host of the Vail Jazz Festival each summer and an annual Winter Jazz Series, both of which feature internationally renowned artists. Additionally, Vail Jazz presents educational programs throughout the year with a particular focus on young musicians and young audiences. Many Vail Jazz shows and educational programs are presented free of charge. This column is a reworking of the original archived edition, republished to commemorate Vail Jazz’s 25th anniversary in 2019. For more information on upcoming performances, visit


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