Bobbysoxers loved him for his androgyny.

During the Capitol period Sinatra’s voice is no longer quite as impressive or as naturally pleasing as when he was known as “the Voice.” It has lost range; he now has to strain for high notes. It has been roughened by experience and by all the cigarettes he has smoked. (“The cigarettes you light, one after another, / Won’t help you forget her, and the way that you love her”: “Learnin’ the Blues.”) The voice has grown deeper, fuller, older. The boyishness that showed in the songs he recorded with the Harry James and Tommy Dorsey bands is long gone. The paradox is that Sinatra in the 1950s hasn’t as great a voice and yet is a greater singer. The difference lies in his command of fast tempos in such Riddle-arranged masterpieces as Songs for Swingin’ Lovers! (1956) and A Swingin’ Affair (1957). But the superiority of the fifties Sinatra extends to ballads also, because he now seems to have perfected the uncanny ability to make a song come to life, to turn it into a chapter of his autobiography, as when, accompanied by a lone piano, he lights a cigarette and sings “One for My Baby (and One More for the Road),” which gets a lot of people’s votes as Sinatra’s greatest saloon song.

Oh, yes—you wanted to know the meaning of swing , the word that recurs so often in Sinatra’s album titles? Listen to “All of Me” on Swing Easy (1954). This is a song Sinatra sang frequently in the 1940s, each time experimenting a little more with the phrasing and with how he exits from the song. Here he sings the final stanza with such exuberance as to undo the actual sense of the words; it’s what is meant by “kidding the lyrics.” Where the line as written would require him to sing “can’t you see, I’m no good without you,” he sings “can’t you see, I’m just a mess without you.” The emphatic mess sounds more like a triumphant declaration of independence than a suitor’s plea. The lyrics say one thing, the delivery says another, and the style makes it cohere. That’s one way swing works.

When Sinatra was Dorsey’s boy singer, he approached the editor of Metronome and lobbied to be put on the cover. “There’s only Crosby and me, and he won’t be around forever,” Sinatra said.


After Sinatra died, I overheard somebody say that he was overrated: “Without his voice he would have been nothing.” There must be a rhetorical term for such a statement.

“Sinatra’s voice went through range changes. His sound changed. He went from the violin with Axel [Stordhal, Sinatra’s primary arranger in the 1940s], the pure violin sound, to the sound underneath, the viola, with Nelson [Riddle]” (lyricist Sammy Cahn). “The voice itself would evolve over the years from a violin to a viola to a cello, with a rich middle register and dark bottom tones” (Pete Hamill).

Early on, Sinatra’s baritone borders on the tenor. He sings with ease though never quite as effortlessly as Crosby. He sings with unusual tenderness and the ability to express longing and aspiration and heartbreak. He also articulates the lyric with absolute clarity. He has amazing range: His deep, rich baritone can reach sublime heights and can sustain the note, thrillingly, as at the end of Jerome Kern’s great love song “All the Things You Are” (1944).

Already in his first recordings you get a sense of that narrative ability, his way of turning a lyric into a short story. Songs like “Falling in Love With Love” (Rodgers and Hart) and “Stormy Weather” (Harold Arlen) and “Where Is My Bess” (Gershwin) and “Fools Rush In” (lyrics by Johnny Mercer) turn into dramatic events, stories that unfold in a performance that combines marvelous singing and a natural gift for (method) acting.

Listen to “I’ll Never Smile Again” (1940), Sinatra’s first major hit with Dorsey. Sinatra and the Pied Pipers, the band’s vocal group (among them Jo Stafford), begin the song with a chorus (“I’ll never smile again / Until I smile at you. / I’ll never laugh again”), and then Sinatra alone and unadorned completes the quatrain: “What good would it do?” When you hear him sing this line, you will understand right away why the first of his nicknames was “the Voice.” Later, in the Rat Pack days of the 1960s, he became “Chairman of the Board,” the guy who had his own record company, Reprise, and could make anything—well, just about anything—happen. When he came back from retirement in the 1970s, he refashioned himself as “Ol’ Blue Eyes.” But in the 1940s he was the Voice, who could ascend to the summit of high notes and stay there, as at the end of “Ol’ Man River” (1945). Jerome Kern, who wrote the music for “Ol’ Man River,” said, “My idea with that song was to have a rabbity little fellow do it—somebody who made you believe he was tired of livin’ and scared of dyin.’ That’s how you do it, Frankie.”