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 for forever changing 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 through the 90s. Dropping out of high school with no formal musical training, he could not read music, but rose from teen idol to living legend. His first hit, “All or Nothing at All”, predicted his future and summed up 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 also his “bad boy” side, 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.

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 stated that a performance oscillates when it uses “a rhythmically coordinated manner…to command a visceral response from the listener (to stamp feet and nod heads).” If you still don’t understand what swing is, listen to “I’ve Got You Under My Skin” from “Songs for Swingin’ Lovers,” one of Sinatra’s greatest recorded songs. If you still don’t understand, I suggest you focus your listening on polka music.

To improvise in jazz is to compose on the spot. Techniques such as singing behind the beat, emphasizing the words, and changing the phrasing (grouping the lyrics together in a different way than the composer wrote them, but which suits the singer’s sensitivity as to how the lyrics should be performed), edit and replace lyrics all allow a singer to make a song their own. Essentially, using these techniques, the singer becomes the composer of a new song and if the singer can get the listener to stomp their feet, click their numbers, or nod their head, you have a jazz singer.

Sinatra’s swagger and cocked hat said he was a jazz musician, but attitude and attire aren’t 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 bona fides as a jazz singer. He’s recorded ‘Swing Easy’, ‘Songs for Swingin’ Lovers’ and ‘A Swingin’ Affair’, but branding is one thing and swinging is another.

At the end of the day, you have to be able to deliver the goods and “the chairman of the board” could do that. Learning early in his career to sustain long, uninterrupted phrases without pausing to catch his breath allowed him to be adventurous with the phrases of a song. Sinatra admired many instrumental jazz soloists and used similar phrasing in his performances. His diction was impeccable but still had a conversational quality. He had an incredible sense of timing. This allowed him to alter a sentence so that the beat did not always coincide with the end of a rhyme, but created a sense of sincerity making the lyrics more personal and leading the listener to believe the story being told. In fact, he has been quoted as saying, “When I sing, I believe. I’m honest.”

Howard Stone is the founder and artistic director of Vail Jazz, the presenter of the annual Vail Jazz Festival each summer and an annual Winter Jazz Series, both of which feature internationally acclaimed artists. Additionally, Vail Jazz presents educational programs throughout the year with a special focus on young musicians and young audiences. Many Vail Jazz shows and educational programs are presented free of charge. This column is re-adapted from the original archived edition, republished to commemorate Vail Jazz’s 25th anniversary season in 2019. For more information on upcoming performances, visit

Ada J. Kenney