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.”