Sinatra expressed regret without selfpity, pain with no loss of masculinity. The poet Carolyn Kizer reasons that the bobbysoxers of the 1940s lost their hearts to young Frankie because he was androgynous, combining masculine and feminine traits, his big voice coming out of his undernourished body. As Crosby sang in a comic 1944 duet with Sinatra, “How can that voice come out of nowhere?”

Sinatra was the first boy singer to prompt mass teenage female hysteria. The breakout event took place three months after the singer had left the Dorsey band. He wanted to make it on his own, not as part of someone else’s Big Band. In a life of gambles this was a spectacular one. On December 30, 1942, Benny Goodman and his sextet were performing at the Paramount Theater in New York. Sinatra’s solo performance was the last act. The singer began and the girls let out their shrieks. Goodman was startled. “What the f— was that?” he exclaimed. That was the moment the Frank Sinatra “phenomenon” began.

“I discovered very early that my instrument wasn’t my voice,” Sinatra said. “It was the microphone.”

When Sinatra joined Tommy Dorsey, Jo Stafford noted how thin he looked, “almost fragile-looking. When he stepped up to the microphone, we all smirked and looked at each other, waiting to see what he could do. The first song he did was ‘Stardust.’ I know it sounds like something out of a B movie, but it’s true: Before he’d sung four bars, we knew. We knew he was going to be a great star.”

With the Dorsey band, Sinatra and Connie Haines and the Pied Pipers sang “Oh! Look at Me Now” (1941), a great upbeat number that has a crucial role in the allegory of Sinatra’s career. It expresses the exultation of having arrived, just as “All or Nothing at All” (1939) states the uncompromising nature of the singer’s propositions and personality. Sinatra sings “Oh! Look at Me Now” with great gusto on A Swingin’ Affair (1957).

Another allegorical Sinatra title is “Why Try to Change Me Now?” (1952), the last recording he made for Columbia Records, with whom he had recorded ever since striking out on his own in 1943. The song is widely interpreted as a parting shot at Mitch Miller, Columbia’s chieftain, with whom Sinatra had long feuded. In September 1953 Sinatra was overheard on the phone saying, with characteristic bravado, “Hey, I just fired Columbia.” What happened was a little more complicated: Columbia had decided to drop him, and the feeling of good riddance was mutual. But Sinatra and his fans never forgot the idiotic novelty songs that Miller obliged him to cut (“Mama Will Bark”), and in Las Vegas many years later, when Miller offered to shake hands, the seated Sinatra, surrounded by friends, looked up and said, “F— off.” Sinatra was great at holding a grudge.

The battle of the baritones: If I were a disc jockey, I would begin an hour by playing Jack Leonard (“In the Still of the Night”), then Perry Como, Bob Eberly (“Brazil”), Vie Damone maybe, definitely Dick Haymes (“It Might as Well Be Spring”), Mel Torme (“That Old Feeling“), saving Sinatra for last (“Imagination”). After a break I’d play something by Crosby, the gold standard of the period (though I’d probably pick a Crosby recording of the previous decade, “Pennies From Heaven”). I think I’d also play a song Sinatra sang about three of his rivals who were “breathing on [his] neck.” “Dick Haymes, Dick Todd, and Como,” a parody of the nowobscure “Sunday, Monday, and Always,” had lyrics specially written by the Sinatra loyalist Sammy Cahn. The song appears on the V-discs Sinatra cut for U.S. troops during World War II. When, in the middle of the song, he substitutes “Perry” for “Como” and in a spoken aside says, “That’s the other guy’s first name,” you grasp in an instant the difference between Sinatra the voice and Sinatra the mouth. The singer’s voice was the voice of an angel, pure in diction. But the mouth was always Hoboken. The song ends: “There’s room for all of us. / There’s just one Crosby. / There’s room for all of us.”

He described the Rat Pack as “just a bunch of millionaires with common interests.”

Before his first solo performance at the Paramount, Sinatra told Johnny Mercer, “I’m going to sing Bing’s ass off.”

From Tommy Dorsey, 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. Sinatra worked hard at it. He swam for hours in swimming pools, frequently underwater, to develop this capacity. Earlier, Harry James had encouraged him to learn to jump rope.

With the Dorsey band he sang “Polka Dots and Moonbeams” and “How About You?” and “I’ll Be Seeing You” and “Without a Song.”