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WITH THE DORSEY band Sinatra sang “I’ll Never Smile Again,” “Polka Dots and Moonbeams,” “How About You?,” “I’ll Be Seeing You,” “Without a Song,” “Everything Happens to Me,” “There Are Such Things,” “The One I Love Belongs to Somebody Else,” “East of the Sun,” “Oh! Look at Me Now,” “Frenesí.” If you were to play one tune from the Dorsey period that could stand as a model for an imaginative big band vocal arrangement, you might choose the jubilant escape song “Let’s Get Away from It All,” in which the protagonists plan to visit all the forty-eight states of the union. Connie Haines: “I’ll get a new Southern drawl.” Sinatra: “Another one?” The Pied Pipers get to joke about a second visit to Niagara, which was shorthand for honeymoon and was therefore a socially acceptable way to talk about having sex— “This time we’re digging the falls.”

From the start, Sinatra worked to improve his technique. Harry James encouraged him to learn to jump rope, to gain strength and lung capacity. But it was from Dorsey’s mastery of the trombone that Sinatra learned a critical lesson in breath control: how to stretch a note, or link the last note of one phrase with the first note of the next, without pausing for breath. Sinatra worked hard at it. He swam for hours in swimming pools, with long stretches underwater, to develop this capacity.

You’ll hear Sinatra sing past a stanza break—or negotiate the transition from bridge to chorus seamlessly—in “Without a Song,” where he glides from the end of the bridge (“in my soul!”) through the beginning of the final chorus (“I’ll never know”). You’ll hear something similarly breathtaking in “April in Paris.” In “My Funny Valentine,” his voice closes the gap between the penultimate line (“Stay, little valentine, stay!”) and the final phrase (“Each day is Valentine’s Day”). Similar feats of vocal artistry are to be found also in the early “Fools Rush In” and “Put Your Dreams Away” and, decades later, in a late live performance of “The Shadow of Your Smile.” Sinatra can hold a note for longer than seems humanly possible before moving into the next musical phrase.

I have always thought of this trick of his as a musical equivalent of the way the liaison works in French pronunciation—where the end of one word melts or slides into the beginning of the next one. The gap between the words, or notes, is eliminated. The voice dominates the silence. It’s as if there were a foot pedal to extend the life of the sound. On the radio I just heard him do “Don’t Worry ’Bout Me” at a late concert. His voice could no longer do certain things, but he still managed the liaison between the title phrase and “I’ll get along.” Most singers would pause to breathe. It is the natural thing to do. Not Sinatra.

Nor is this mere virtuosity. The point of the gesture is to convey depth of emotion.

A comparison to Marlon Brando is in order. “As a singer Sinatra prided himself on his clear diction, yet it could be said that he developed close musical equivalents of the Brando mumble,” the literary scholar Roger Gilbert writes. “His slurring portamentos and glissandos, his tendency to stay behind the beat, his willingness to let hints of raspiness enter his voice, his sudden shifts of dynamic and timbre, all these become part of an expressive vocabulary that does with musical notes what a Method actor does with words.”*