“My Way” or the Highway?

I probe the depths of my Frank Sinatra anxiety, and tell how I came to terms with his blowhard's anthem


I’m a Frank Sinatra fan, but I went on a long, hard road to get there.

I never doubted his phrasing or his charisma or his stage presence—those are wickedly good. In some ways, they’re unsurpassed. As a student of the American popular song, especially those middle decades of the 20th century, which some have legitimately called its Golden Age, you almost have to start by taking stock of Sinatra. Not only did he sing the songs, in many instances he defined them. There are perhaps a handful of other singers at that level, but it’s a short list, and they loom so large on the landscape that you only need one name to identify who you’re talking about—Louis, Bing, Billie, Ella, and maybe two or three more.


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That’s the elevated level where Sinatra operated, and remained for decades. He was doing it his way before Charlie Parker and Miles Davis, before Buddy Holly and Elvis Presley, before the British Invasion and the Beatles. And he was doing it his way after they were gone. He had a half century at the top

But his worldview and all its assumptions disturbed me. He operated out of a self-centered pose—infused with a vanity and smugness that no one has surpassed in the many decades since his death. The narcissism still bothers me, even though I’ve come to terms with his artistry. And Sinatra’s point-of-view is embedded in those performances. You can’t separate the man and his music. In many ways, that was part of his greatness. His personality is everywhere on display on those records.

“Half of me thinks that ‘My Way’ is absurd and embarrassing; but the other half believes it might be the defining American song of the second half of the 20th century.”

Just compare Sinatra with those other gold standard vocalists mentioned above. Did Billie Holiday ever sing a boastful song in her entire life? I can’t think of one; even when she dealt with boastful lyrics (as on “I Can’t Get Started”) she came across as more wistful than conceited. Or consider Louis Armstrong, whose onstage personality was every bit as large as Sinatra’s—how many singers can make that claim—and he even inserted his name into lyrics (“Hello Dolly. This is Louis, Dolly….”). But with his larger-than-life presence, Armstrong was celebrating his joie de vivre, a love of life, not a love of self.

Perhaps the most revealing comparison is Tony Bennett, who is often seen as operating from the same playbook as Sinatra. But Bennett is almost ego-less in his interpretations of the song, focused entirely on bringing the lyrics to life. I say almost, because Bennett wisely realizes that the narrator must sometimes enter into these songs to give them full meaning, and his ego shows up to play that role, but only to the extent demanded by the song.

Sinatra, in sharp contrast, can take a song delivered entirely in the third person, such as “The Lady is a Tramp”—where you will seek in vain for an I or me, or we in the lyrics—and still make you feel as if he’s the leading character in the story. That, too, is a rare achievement, but also a reminder of how different Sinatra was from every previous popular singer. None of them dominated the songs with such insistence. Even when he sang the very same tunes as these others, the end result was infused with his swagger at every turn.

In fact, that’s what the fans loved most about him. I might even suggest that, for many fans, they didn’t just want to hear Sinatra, they wanted to be Sinatra. Or perhaps, for the most ardent admirers, they waned to be with Sinatra—in what the newspapers once called, with their skill in circumlocution, compromising situations. He was the focal point for fantasies, and often the most puerile.

Yet here’s where it gets tricky for a music critic. As much as I want to dismiss Sinatra for these attributes, I also recognize that he was the most emblematic musician of his generation. And precisely because of this strutting and posing. America craved a musician of this sort. If there had been no Sinatra, they would have needed to invent one.

The United States at the midpoint of the 20th century was ready to throw off all the shackles imposed by the Great Depression and two World Wars. People wanted to cultivate their egos—and for the simple reason that they’d never had the chance before. The first stirrings of this could be felt in the various counter-culture and bohemian movements of the 1950s, but the “me generation” took center stage in American culture with a vengeance in the 1960s.

Sinatra was no beatnik or hippie, but he made those rebels possible. He did it by asserting his extreme individualism, by questioning conventional values, by acting as if he were above the rules. And to some extent, he was above the rules. Who else could take care of an enemy with a quick phone call to a Mafia don? Who else could cavort with starlets as if it were his droit du seigneur? Who else could waltz into the White House, in both Democrat and Republican administrations, and act as if he owned the place?

By the way, someone close to the Reagans told me that Nancy Reagan listened to those Sinatra albums over and over again. And I don’t even want to dwell on what Sinatra delivered for JFK. But just think: Even if you were the most powerful couple in the world, Sinatra still inflamed your fantasies.

Can you get any higher?

When Michael Jackson was the hottest musician in the world, his producer Quincy Jones decided that there was one last lesson his superstar client needed to learn—and only Sinatra could teach it. One evening, he took Jackson to a Sinatra concert, and told him to pay close attention. “Halfway through the show,” Jones later related, “Michael whispered in my ear: ‘He walks like a king.’”

You need to realize that Sinatra was forty years into his music career at that juncture. He had never been genuinely handsome, by my definition—although I’m sure many will disagree with that assessment—but even starry-eyed fans must have noticed the wear and tear long before Michael Jackson went to that concert in the early 1980s. Even the toupee Sinatra wore on stage didn’t help much, and soon he would need a teleprompter to keep track of the lyrics. Yet still. . . he walked like a king. Sinatra was larger than life even in his decline, an emperor parading before the masses in the global pop culture colosseum, and still somehow tapping into a strange sexual/macho charge that kept audiences enthralled and begging for more.

So here’s my quandary. How can I argue with Sinatra if he captured the whole ethos of an era better than anyone else. Maybe I’m queasy about the ethos. But, hey, I should take that up with God, not Ol’ Blue Eyes.

For me, all these complex valences reach their peak in one song. And you know which one I’m talking about.

I've lived a life that's full
I've traveled each and every highway
And more, much more than this

[PAUSE FOR DRAMATIC EFFECT]

I did it MY WAY!

How can I not find this song annoying? On the other hand, when it comes on the radio, I never turn it off. I listen all the way to the end. Sometimes I even sing along.

Half of me thinks the whole thing is absurd and embarrassing; but the other half believes it might be the defining American song of the second half of the 20th century.

Sinatra didn’t always sing songs like this. It wasn’t until the 1960s that he started making a specialty of tunes that proclaimed the glories and victories of his life. One of his trademark songs from that period is even called “That’s Life” (1966), where he celebrates winning, winning and even more winning. And just a few months earlier, he had tilled that same fertile soil with “It Was a Very Good Year,” where he describes his life as a fine “vintage wine.”

For those (like me) who prefer the 1950s Sinatra recordings on the Capitol label, these songs about a victorious life on the top are more than a wee bit grating. Yet if anyone had the right to sing about life at the top, it was clearly Frank Sinatra—especially now that he was in his 50s and had pretty much bought, taken, seduced, and whacked everything in his path.

“My Way” comes after these other songs—in fact, at a time when most of Sinatra’s hit singles were already behind him. But also, it arrived at a juncture when he could view the pop culture scene and recognize so much of it as a pale imitation of his own worldview. Almost at that same moment, psychoanalyst Heinz Kohut was redefining narcissism as a normal part of the human psyche. It was okay to love yourself a little, or even a lot—and no one sang of that self regard with more triumphalism than Frank Sinatra. Hippies and others could strive for self-actualization, but Sinatra had actually composed its soundtrack.

In short, America wanted a song like “My Way,” and there was only one person who could sing it the way it needed to be sung. Perhaps the only surprise is that Sinatra didn’t actually compose it. “My Way” borrows the music of "Comme d'habitude," a French song with more conventional love lyrics. Paul Anka acquired the English adaptation rights, and wrote new lyrics—but with Sinatra specifically in mind. (Are you surprised?).

“If the ego were a country, this would be its national anthem. And Sinatra delivered it with a kind of cult-of-personality authority that few below the pay grade of dictator have ever managed to muster.”

Anka had recently dined with Sinatra and some of the latter’s mob associates, and the Chairman of the Board had expressed a kind of world-weariness only a monarch long on the throne can feel. He even talked about retiring from music. Anka knew that there was a song in all this. As he describes it:

“At one o'clock in the morning, I sat down at an old IBM electric typewriter and said, ‘If Frank were writing this, what would he say?’ And I started, metaphorically, ‘And now the end is near.’ I read a lot of periodicals, and I noticed everything was ‘my this’ and ‘my that.’ We were in the ‘me generation’ and Frank became the guy for me to use to say that. I used words I would never use: ‘I ate it up and spit it out.’ But that's the way he talked. I used to be around steam rooms with the Rat Pack guys—they liked to talk like Mob guys, even though they would have been scared of their own shadows.”

The next day, Anka phone Sinatra at Caesars Palace. Yes, Caesars Palace—you can’t make this stuff up, because the reality is already pitched at such an extreme point of absurdity—and told the world-beating singer that he had written a world-beating song that only he could sing. Sinatra recorded it in a single take on December 30, 1968, and the rest is history.

Even in an age of rock, listeners took notice. This was more than a song. If the ego were a country, this would be its national anthem. And Sinatra delivered it with a kind of cult-of-personality authority that few below the pay grade of dictator have ever managed to muster. To his credit, he expressed private reservations about the song. “He always thought that song was self-serving and self-indulgent,” daughter Nancy Sinatra has related. “He didn't like it. That song stuck and he couldn't get it off his shoe.”

But that hardly mattered. The public ate it up. And even when Sinatra wasn’t singing it, others stepped in to fill the breach. I can hardly imagine a better candidate than Sid Vicious of the Sex Pistols, who could never have found a more fitting vehicle for his own punk hauteur, although he had to change the lyrics to fit in some of those seven famous words not allowed on TV.

The music’s afterlife would seem bizarre, but only if you don’t understand the psychological exhibitionism of modern life. For example, it might seem a total mystery how this song got so popular with karaoke singers. It’s hard to sing, and not especially enjoyable to hear delivered out-of-tune. But what intrepid salaryman on the stage can resist unleashing his inner Sinatra, even if only for just the four-and-a-half minutes duration of the song?

For what is a man, what has he got?
If not himself, then he has not.

By the way, I’m told this song is frequently programed at funerals. I think I’ll stick with Ave Maria, but for those who want to swagger up to the pearly gates, this tune can’t be topped. And if you’re not planning on paradise in the next life, at least this corpse did it all while still above ground.

For less equivocal personal enjoyment, I will still opt for Sinatra’s earlier recordings. Those classic albums from the 1950s, when he sang about a broken heart, are still my favorites. And I probably have more interest in those very old Sinatra tracks from the early 1940s than most of his fans, savoring that brief period when his vocal work flourished without the slightest touch of irony or metanarrative self-referentiality.

But I have made my peace with those strutting and preening songs of his later days, even with this blowhard’s anthem. Love it or hate it, I can’t ignore it. And let me say, and not in a shy way, that many years from now, when musical archeologists try to decipher the inner lives of average people of the American Century from the songs they loved, this will probably be Exhibit A in Chapter One. For better or worse, we didn’t just hear this song; we lived through it too.