100 years of Frank Sinatra and jazz

Do you think of Frank Sinatra as a jazz singer? As we celebrate his 100th birthday, guest author Eric Felten explores this question.

When Frank Sinatra took the stage at the 1965 Newport Jazz Festival, the "jazz purists" were unhappy (so said Variety). Unhappy not because of "his own brand of casual hipness" nor even because of his Vegas-honed "glamour showmanship"—an aesthetic that included leaving the festival by helicopter like some stadium rock star; no, the purists' problem was that Sinatra was "technically not a 'jazz singer.'"

Frank Sinatra in hat and tie stands at microphone with music stand in front of him, mouth slightly open

Not a jazz singer? Says who? It's a debate that has persisted, and still has some relevance. What, after all, was the Smithsonian Jazz Masterworks Orchestra doing presenting a Sinatra centennial concert if the man's music can't credibly be called "jazz"?

It depends, of course, on what one expects from a jazz singer. Sinatra rarely strayed far from a melody; he didn't sing the blues; he didn't scat (unless one counts "doo-be-doo-be-doo" at the end of "Strangers in the Night," the less said about which the better). But he did swing—was one of the great champions of swing—and without that jazz idiom underpinning everything he did, Sinatra never would have achieved his undeniable status as the greatest interpreter of the Great American Songbook.

Saxophonist Lester Young clearly thought Sinatra was up to snuff, jazz-wise: "If I could put together exactly the kind of band I wanted, Frank Sinatra would be the singer," he said. "Really, my main man is Frank Sinatra." (Sinatra would eagerly return the favor: "We had a mutual admiration society," he said of Lester Young. "I took from what he did, and he took from what I did.")

Black and white photograph of Frank Sinatra on stage under a spotlight, holding microphone in left hand

And after all, it was jazz that saved Sinatra's career, after it had become mired in Columbia Records producer Mitch Miller's dismal concept of what made a hit record—two parts treacle to one part novelty. Miller pressed Sinatra into notorious atrocities such as "Mama Will Bark," sung as a duet with a tone-deaf actress named Dagmar. But once Sinatra had escaped Miller, the question was how he would differentiate his new Capitol Records sound from his old Columbia Records output. Capitol's producers found the answer in the sophisticated swing arrangements being penned by a young house arranger, Nelson Riddle.

Riddle's arrangements remain the essential Sinatra sound. They start off with that distinctive two-beat that Riddle pilfered from the Jimmie Lunceford band (to hear where that Sinatra groove comes from, listen to Lunceford's 1935 recording of "My Blue Heaven"). Then, following the ease of that two-beat, comes a hard-swinging 4/4 with Frank's phrasing driving the rhythm every bit as much as the bass and drums.

Color painting of Frank Sinatra singing, eyes closed

Nowhere is the concept more perfectly executed than in Riddle's arrangement of Cole Porter's "I've Got You Under My Skin." It starts with an easy two-beat riff; Sinatra sings the song beautifully and (perhaps more important) knowingly; then the band builds and builds through layered riffs, exploding into Milt Bernhart's hard-swinging trombone solo; when Sinatra comes back in, he somehow manages to ratchet up the energy and excitement a notch or two more, wailing "Dooooon't you know, little fool…" And then after that cascade of climaxes the whole thing is neatly buttoned up with a tidy double-bass coda.

"Under My Skin" remains a high point of 20th-century American culture—and if it doesn't count as "jazz," more's the pity for jazz.

Through the '50s and '60s, Sinatra would work with many of the greatest arrangers in jazz and swing and orchestral pop—not only Riddle but Billy May, Neal Hefti, Quincy Jones, Johnny Mandel, Don Costa, and Gordon Jenkins. The ace Los Angeles studio groups that usually backed him included such jazz masters as trumpeter Harry "Sweets" Edison, bassist "Little Joe" Comfort (who happened to teach a young Charlie Mingus how to play), and drummer Alvin Stoller. Sinatra, whose apprenticeship was with the bands of Harry James and Tommy Dorsey, would continue to perform with essential jazz big bands—Woody Herman, Duke Ellington, and most compellingly, Count Basie.

Album cover with color photo of Frank Sinatra winking and beckoning

All along the way, Sinatra operated at the intersection of pop and jazz, even as jazz began to move away from its popular roots as dance music. At a time when jazz was succumbing to a tendency to ramble—please, oh please, no more seven-minute bass solos!—Sinatra and his arrangers proved time and again what could be accomplished in three minutes and change. And though the Chairman's comic stage-show interludes were excruciating—please, oh please, no more Sinatra "monologues!"—when the singer was singing, he proved time and again that high art and entertainment can coexist.

Sinatra did not call himself a jazz singer, choosing to identify himself, instead, as a "saloon singer." That label captures a moment when jazz was the province of juke joints, and the music was about love, lost or found, when swing could bring both swagger and solace. Now, 100 years after Sinatra was born, jazz musicians still—or maybe more than ever—have much to learn from Frank.

Eric Felten is a writer and jazz musician in Washington, D.C.