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Pretty soon he won a Major Bowes contest and landed a 39-week contract as lead singer in a quartet called "The Hoboken Four." Six months later, Sinatra was back in Hoboken, airing his talents on 18 local sustaining programs every week for only 70¢ a week carfare. He also sang in the Rustic Cabin, a roadhouse not far from Hoboken, where he waited table too, and "practically swept the floor," for $15 a week. And there it was, in 1939, that Frank Sinatra got his break.
Bandleader Harry James heard Frank sing, and took him on as a featured vocalist. Six months later the great Tommy Dorsey himself bought Frank away from Harry at the princely price of $110 a week. Two years with the Dorsey band smoothed a lot of rough edges off the kid from Hoboken, and raised at the same time some alarmingly sensual yet sensationally effective bumps on his singing style.
Sinatra would appear onstage, looking, as one contemporary described him, "like a terrified boy of 15 in the presence of his first major opportunity." He would hang for a moment on the microphone, holding it itchily, as if it were a snake. "His face was like a wet rag." His chest caved in, as if from the weight of the enormous zoot shoulders it bore, and a huge, floppy bow tie hung down like the ears of a spaniel. For a moment he would look among his audience, pleadingly, as if searching for his mother, and then he would begin, timidly and with trembling lips, to sing.
Worn Velveteen. The Voice was worth all the buildup. It sang slowly, more slowly than most popular singers dared to sing, but it kept a heavy, heartbeat rhythm. Says one critic: "He never let go of that old Balaban & Katz beat.'' Other critics compared the sound of his voice to "worn velveteen," or said it was "like being stroked by a hand covered with cold cream." One listener wondered if Frank tucked his voice under his armpit between numbers, and another said he sounded as if he had musk glands where his tonsils ought to be.
Whatever the sound was, it was most consciously contrived. From Bing, of course, Frank borrowed the intense care for the lyrics, and a few of those bathtub sonorities the microphone takes so well. From Tommy Dorsey's trombone he learned to bend and smear his notes a little, and to slush-pump his rhythms in the long dull level places. From Billie Holliday he caught the trick of scooping his attacks, braking the orchestra, and of working the "hot acciaccatura"—the "N'awlins" grace note that most white singers flub.
Yet through all these carefully acquired characteristics ran a vital streak of Sinatra. He was the first popular singer to use breathing for dramatic effect. He actually learned to breathe in the middle of a note without breaking it (an old trick of the American Indian singers), and so was able "to tie one phrase to another and sound like I never took a breath." He carried diction to a point of passionate perfection. But what made Sinatra Sinatra, when all came to all, was his naive urgency and belief in what he was saying. As one bandleader put it: "Why, that dear little jerk. He really believes those silly words!"