Most fans of American jazz and pop vocalists would agree that Ella Fitzgerald and Frank Sinatra were the undisputed champs of their era. But in 1959, both at the height of their artistic prowess, Sinatra ceded the top spot, admitting, “Ella Fitzgerald is the only performer with whom I’ve ever worked who made me nervous. Because I try to work up to what she does. You know, try to pull myself up to that height, because I believe she is the greatest popular singer in the world, barring none—male or female.” The feeling was mutual, and they duetted on several high-profile occasions. Fitzgerald adored Sinatra, deeply respected his talent and, given her natural humility, would never have claimed superiority.
The career arcs of these two giants were eerily similar, beginning with their rough-and-tumble adolescences. Fitzgerald was born in Newport News, Va., in 1917 but raised in Yonkers, as the crow flies about 15 miles north of Sinatra’s hometown, Hoboken, N.J. Sinatra, born in 1915, was expelled from high school due to misbehavior. Fitzgerald was early on an excellent student, but she began cutting class following her mother’s death in 1932 and was eventually sent to an orphanage and a reform school. He got his big break on Major Bowes’ Amateur Hour radio show in 1935. In November of ’34, Fitzgerald had ignited her career by winning top Amateur Night honors at Harlem’s Apollo Theater, famously aborting her planned hoofer routine when the preceding dance act proved too polished. Instead she sang, choosing Hoagy Carmichael’s “Judy,” whose lyric included the prescient notion “In a hundred ways/You’ll be shouting her praise.”
Before simultaneously launching solo careers in 1942, both were band singers, Sinatra with Harry James then Tommy Dorsey, Fitzgerald with Chick Webb’s hard-swinging orchestra, which she fronted after Webb’s death in 1939. In the wake of correspondingly serious lulls in the early 1950s, both navigated resurgences that lifted them to iconic heights, precipitated by strategic label changes: Sinatra moved from Columbia to Capitol; Fitzgerald transitioned from Decca to producer Norman Granz’s newly minted Verve. Both fought for good songs and, despite plenty of dross in their enormous catalogs, remain the definitive interpreters of the Great American Songbook. They continued to perform into their 70s. Their deaths, like their births, arrived less than two years apart. Fitzgerald passed first, in 1996, due to prolonged complications from diabetes. Sinatra succumbed to a heart attack in May of ’98.
Yet despite the remarkable parallels, Fitzgerald and Sinatra were fundamentally different as singers and as public figures. He sang for, and about, himself; she sang for others. As the New York Times noted in its Fitzgerald obituary, “Where [Billie] Holiday and Frank Sinatra lived out the dramas they sang about, Miss Fitzgerald, viewing them from afar, seemed to understand and forgive all.” Sinatra’s life was an open book; hers was, by and large, a blank page. Her life, though fraught with hardships and heartache, existed almost exclusively for the music and the joy of satisfying listeners. And despite incomparable success—she was the first African-American woman to win a Grammy, and has more performances in the Grammy Hall of Fame than any other female artist—Fitzgerald forever maintained a demure, often self-effacing modesty, coupled with a shyness propelled by a constant fear of appearing inarticulate.
During a celebrity-packed salute at New York’s Basin Street East in 1954, she acknowledged a slew of accolades by quietly stating, “To know that you love me for my singing is too much for me. Forgive me if I don’t have all the words. Maybe I can sing it and you’ll understand.” Three and a half decades later, when accepting the Society of Singers’ inaugural lifetime achievement award, named in her honor, she softly observed, “I don’t want to say the wrong thing, which I always do; but I think I do better when I sing.” We remember Sinatra—to whom she presented the Society’s second annual “Ella” award—as much for the fisticuffs and high-flying revelry as for the Voice. Fitzgerald we revere exclusively for the immensity of her musical skills and the intrinsic, altruistic warmth that helped define them.