The Riddle of Sinatra
Frank Sinatra had been headlining at New York’s Copacabana since the end of March 1950 when he took to the nightclub’s stage late on April 26 for that Wednesday evening’s last set. Only about 70 customers, less than 10 percent of the Copa’s capacity, were still in attendance. Around 2 a.m., Sinatra opened his mouth to sing—and nothing came out. “Just dust,” he said later. His audience stared. He stared back. Bandleader Skitch Henderson thought Sinatra was fooling around. “But then he caught my eye,” Henderson recalled. “I guess the color drained out of my face as I saw the panic in his.” Finally, the singer whispered “Good night” and walked offstage, where he began coughing up blood. His vocal chords had hemorrhaged. Doctors told Sinatra not to talk for at least a week. He canceled a booking in Chicago.
Sinatra’s career had already been in a nosedive. Now he entered a wilderness period that saw him forced to produce musical drivel, until Capitol Records took a chance on him. The label paired the singer with arranger Nelson Riddle, a collaboration that revitalized Sinatra’s studio work. Embraced in Riddle’s artful, sophisticated orchestrations, Sinatra reinvented himself for adults—as an exuberant swinger on upbeat albums or a broken-hearted brooder on introspective outings. His collaborations with Nelson Riddle were the mold that reshaped Frank Sinatra into the cultural icon familiar today.
Sinatra had been on top of the world. The Hoboken, New Jersey, native knew from boyhood that he wanted to be a singer. He was working as a singing waiter at the Rustic Cabin, a roadhouse in Englewood Cliffs, New Jersey, when trumpeter and bandleader Harry James came in one evening to size up the local talent. James hired Sinatra in February 1939, paying his protégé $75 a week.
Soon Sinatra was aiming higher—at the country’s top band, led by trombonist Tommy Dorsey. In January 1940 Sinatra left magazine in 1965. “Why couldn’t a singer do that, too?” Sinatra also listened to violinist Jascha Heifetz, noting how Heifetz maintained a melody line without taking a break. “It was my idea to make my voice work in the same way as a trombone or a violin—not sounding like them, but ‘playing’ the voice like those instruments.”
