Looking Back on 50 Years of Popular Music, a Critic Has Two Words for Sinatra: 'the Best'

So varied and vivid is his personality, generating both ugly public tantrums and gestures of unsurpassed generosity, that Frank Sinatra’s celebrity seems often to overshadow his singing. His famous friendships, in low and high places—at the request of his old pal Ronald Reagan, he is producer and director of this week’s Inaugural gala—have distracted repeatedly from the impeccable talent. But he has been a major recording star—often the major recording star—for most of his 50 years as a professional vocalist. An idol emeritus, who today still travels the cabaret, concert and benefit circuits, he is described by critic John Rockwell, in Rockwell’s new book Sinatra: An American Classic (Random House/Rolling Stone Press, $29.95), as “by any reasonable criterion the greatest singer in the history of American popular music.” Rockwell, 44, a Harvard graduate with a Ph.D. in cultural history from Berkeley, plies his critic’s trade at the New York Times, covering both classical and popular music. He discussed his assessment of Ol’ Blue Eyes with Senior Editor Ralph Novak.

Why do you rank Sinatra in a class by himself?

Sinatra has given people pleasure for a half century. He’s a born entertainer with a pleasing light baritone, a natural musicality and sense of phrasing. He has an easy, fluent, liquid style, and his career cleverness—an intuitive focusing on the self—hasn’t hurt.

You mentioned Sinatra’s “phrasing,” as a lot of people do. What does that mean?

It’s how you weight and balance notes, words and sounds to do justice to a song, to blend abstract musical virtues with the poetic virtues of the lyrics.

Can you think of an example?

Listen to the way he sings the line “Give me one for my baby and one more for the road” on his Only the Lonely album from 1958. He lingers on the word “baby” and gives it a downward slide—it’s more like “BAYYYYYYyyyyyyyy-be” really. Then he has to sing the rest of the line faster to catch up to the accompaniment. He does that kind of thing without drawing a lot of attention to it.

Is there anyone you rate close to Sinatra?

There are a lot of singers in different genres—Smokey Robinson, Ray Charles, George Jones. I’ve gotten a lot of calls from Bing Crosby fans who feel their boy is being ignored. I think he was a terrific singer and, in fact, Sinatra has acknowledged his debt to Crosby; he got a lot of his naturalness and expressiveness from Bing. But Crosby did not have as much vocal and emotional range; you can only hear White Christmas so many times.

What about Elvis?

I love Elvis’ music, especially his rock singing. As a singer, though, outside his role as a social force, I often find him wooden and uninteresting, especially in his ballads and middle-of-the-road stuff.

How has Sinatra’s offstage behavior affected the way people perceive him as a singer?

He gives off an image of elegant, powerful and slightly ominous opulence that appeals to people. On the one hand there’s this slightly brutal, finger-popping, tough-guy bravado, on the other an emotional richness, vulnerability, a regret for lost opportunities. Everything feeds into that image—the weird stuff with the press, his mean streak, the generosity, the ease on the stage, the Mafia rumors, the acting skills. They all create a persona that is his vehicle.

Would he have been as great a success if he had been just an average guy?

I started out thinking of this as a test case of the old question, ‘Can you get good art out of a bad guy?’—what you might call the ‘Amadeus syndrome.’ And Sinatra has done lots of things I wouldn’t agree with. But he is, I think, a genuinely emotional man, and he clearly has a right to lash out when he’s angry. And he is crazy like a fox. All that stuff bolsters his image as a feisty guy who won’t take crap from anybody. Every time he gets into a fight and he gets his name in the papers, it just reinforces his image.

Why do you call him a spokesman for his generation?

Throughout his career he has managed to create a style that has reflected—epitomized, really—the concerns of someone the same age as his audience. He’s always sung about romance, love and sex, for the bobby-soxers in the ’40s. Then he took a more swinging, sophisticated approach in the ’50s. And there’s a lot of romantic nostalgia and regret in his albums of the ’60s and ’70s. He has never burned out, and the fact that he has kept going is, to his audience, a reaffirmation of themselves.

Have his politics affected his popularity?

Not in the sense of whether he supported Kennedy, which he did, or Reagan, which he does. The country has gotten older and richer and more conservative, and so has Sinatra.

Does he have a sense of humor?

Clearly he’s a guy who in every aspect of his personal and professional life likes to exercise control. That militates against the kind of relaxed atmosphere that allows for a good laugh. He often issues statements through his press agent, though, and there’s an occasional good line. When Judith Campbell Exner, a girlfriend he had introduced to both President Kennedy and the mobster Sam “Momo” Giancana, said she had broken off her relationship with Sinatra because his sexual tastes were too kinky, he responded, “Hell hath no fury like a hustler with a literary agent.”

How has Sinatra’s singing changed over the years?

He’s always been an experimenter, sometimes out of artistic curiosity, sometimes out of commercial desperation. In the ’50s, for instance, his voice deepened, he threw off his ingenue image and invested some of his new acting skills into his singing, which enabled him to tell a tale better.

What do you think of his singing today?

For a man of 69, his voice is astonishing. It has darkened in pitch and his breath control has weakened, but he has always been very clever about adapting his style to his current vocal state. Now he sings more upbeat songs with short phrases that require less breath control, and when he does ballads he exploits the weakness of his voice as a metaphor for fragility.

Which Sinatra record do you consider his best?

Given my bias for ballads, the album I go back to most often is Only the Lonely, which Sinatra himself names as his favorite. He recorded it in 1958 with Nelson Riddle arrangements, and it features, aside from the title track, One for My Baby, What’s New? and Good-bye.

Which records do you consider his worst?

From his earlier period there was a duet with Dagmar called Mama Will Bark, which included dog imitations. When he tried to do rockoid stuff such as Bad, Bad Leroy Brown it didn’t work at all, and he recorded a disco single of Night and Day that was awful. I’ve hardly met anyone who has anything good to say about The Future record from his Trilogy album in 1980, though The Past tracks were terrific.

Do you see any popular singer today who might be the Sinatra of the future?

Frank Jr. would like to be. But the real answer would have to be someone who synthesizes and epitomizes the singing style of his time and evolves through various stages of his life, someone who represents his generation. If Michael Jackson or Prince could translate what they have now through their whole lives, they might do it. But the closest so far may be Linda Ronstadt, an interpretive singer who was popular with youth when she was younger and is now broadening her appeal.

Did you try to contact Sinatra before writing the book?

Though I did write a perfunctory letter asking for an interview, I was just as glad he didn’t respond. I wanted to write an interpretive essay rather than a biography. I wanted to get to the history of American popular music over the last half century as filtered through one person. I wanted to see if you could talk about Sinatra as a pre-rock avatar, and examine his connection to rock rebellion as an individual who refused to kowtow to old notions of what was accepted, a guy from the wrong side of the tracks who wouldn’t be put down.

Has Sinatra responded to the book?

Someone told me—about third hand—that he is supposed to have said he was “tickled” by it. I’m not sure what that means, but I’d rather hear that than be named in a lawsuit.

Would you like to meet him?

Sure, I’d love to meet him in a way that was natural and nice. But in some ways I know Frank Sinatra already. The best singers put so much of themselves in their singing, you know them from their music.