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‘My Way’ Has Always Been the Anthem of Despicable Men

The Frank Sinatra standard, which even he hated, is the soundtrack to funerals and Donald Trump’s presidency. Why do guys get off on its endless self-pity?

We should have seen it coming. As Donald Trump and his family flew away from Washington, leaving the presidency behind, their well-wishers were left listening to the melodramatic strains of Frank Sinatra’s “My Way.”

CNN’s commentators chuckled, but the song selection was hardly surprising. After all, “My Way” proved to be the bookends of the man’s horrendous White House reign, with him and Melania (and Mike Pence and his wife) awkwardly dancing to a rendition of the song four years ago at their inauguration. It was no less bizarre then. (Nothing like kicking off a presidency with the lyric, “And now, the end is near…”)

Trump has long admired Sinatra — “I have the greatest respect for people who have experienced adversity and then come back,” he once wrote — and you could see why a champion self-pitier like our now-former president would emotionally invest in “My Way.” It’s a song about a guy who’s been kicked in the teeth, knocked around by circumstance, but who remains defiant even so. It’s a song about looking back at the wreckage of the mistakes you’ve made and expressing no remorse. You gotta live your life, right? Regrets are for the weak — it’s a sign of a real man’s character if he barrels headlong from one disaster to the next, confident that if he just trusts his gut, everything will work out as it should.

For what is a man, what has he got?
If not himself, then he has naught
To say the things he truly feels
And not the words of one who kneels
The record shows I took the blows
And did it my way

“My Way” is an incredible song, by which I mean it’s astoundingly brazen and bullheaded. It’s the ultimate “I’m sorry if you were offended by what I said” anthem — the ultimate non-apology apology. Of course Trump would love it.

The song has been around for more than 50 years, and what’s funny is that, like a lot of pop culture Trump digs, he doesn’t really understand it at all — or, at least, how “My Way” has shifted over time. Even the man for whom the song was written came to loathe it — perhaps in part because he didn’t like the associations that “My Way” brought to his persona. In 2021, if you’re blasting “My Way” unironically, you’re doing it wrong.

Back in the late 1960s, “My Way” was the brainchild of Paul Anka, a prolific songwriter who had visited France, where he became enchanted by a tune called “Comme d’Habitude,” about a couple falling out of love. Anka bought the rights for a dollar, although he wasn’t quite sure what to do with the track, which he decided needed new lyrics. “I went back to New York and put it in a drawer,” Anka wrote in his 2013 memoir, fittingly titled My Way. “But I never forgot it was in that drawer — it was in there, palpitating, waiting for the moment I’d awaken it.”

The songwriter wanted to come up with a narrative that “was going to be very dramatic and have a grand sweep to it.” And that’s when he spoke to Sinatra, who had some news: He was through. Now in his 50s, the Chairman of the Board had lost the swagger and also the command of his earlier recordings. “I’m fed up,” Anka says Sinatra told him, “I’m going to do one more album, and I’m out of here.” Bereft at the news that Sinatra was going to be retiring, Anka vowed to write him a song for that farewell album. 

“I’ll never forget that night,” Anka writes in My Way. “It’s about one in the morning, I know there’s a storm moving in, the atmosphere is charged, there’s a sense of drama in the air. I’m all alone, playing this melody on the piano, writing it as if Frank were writing it, in the person of Frank, tuning in Sinatra’s vibe, a sense of foreboding and finality. I get that first line, ‘And now the end is near, and so I face the final curtain.’ The rain is getting heavier. The great legend is leaving the stage, the lights going out. It needed to be operatic, a big, swelling moment. I start typing like a madman — forget the craft, just write it the way he talks. … Little did I know I was to write a song that would ultimately revitalize his career and change the direction of mine.”

Impressed with “My Way,” Sinatra recorded it for his 1969 album of the same name, which proved to be his highest-charting release in three years. “My Way” was never a monster hit — it didn’t even hit the Top 20 — but it nonetheless felt like a signature Sinatra song. “‘My Way’ is [absolutely] Frank,” Capitol Records executive Alan Livingston says in Will Friedwald’s book Sinatra! The Song Is You: A Singer’s Art. “He’s telling you a story there. And it has to be something that he believes in, like ‘In the Wee Small Hours of the Morning.’ … Frank has lived through every conceivable emotion. He’s had unhappy divorces, and lost women he didn’t want to lose, and experienced his career going down the tubes. … I think that actually gives him credibility as well as his ability to interpret a lyric and to phrase it. Because he feels it, he understands it.”

Anka sensed that, too, later admitting that he felt the song more or less wrote itself. In his book, he notes, “[‘My Way’] was a departure for me — I would never under normal circumstances write something so chauvinistic, narcissistic, in-your-face and grandiose. The reason I pursued it was that I knew now that this was for Sinatra and that he could pull it off.” In other words, Sinatra’s public image as an arrogant, controlling, petty womanizer — and, oh right, perhaps the greatest singer of the 20th century — would sell the song’s message. 

Critics tend to consider “My Way” as one of Sinatra’s worst hits. And, certainly, his rendition lacks the subtlety of his great 1950s albums, but still there’s no denying his ability to bring emotion and a sense of autobiography to the song’s wistful tale of an old soul taking one last look around before he fades away:

And now, the end is near
And so I face the final curtain
My friend, I’ll say it clear
I’ll state my case, of which I’m certain
I’ve lived a life that’s full traveled each and every highway
And more, much more than this
I did it my way 

Regrets, I’ve had a few
But then again, too few to mention
I did what I had to do
And saw it through without exemption
I planned each charted course
Each careful step along the byway
And more, much more than this
I did it my way

“My Way” became a concert staple for Sinatra, who came to hate the song, perhaps because of its overblown histrionics — those strings and horns are so brash, you’d swear he’s about to storm a castle — and also maybe because he didn’t like to have to keep reminding his audience that he was reaching the end of his career.

Sinatra’s disdain for “My Way” soon became legendary. Back in 2009, Friedwald wrote an amusing piece for The Wall Street Journal in which he chronicled Sinatra’s litany of times he mentioned, on stage, how much he hated singing “My Way.” (At a 1978 date, the Chairman lamented, “I hate this song — you sing it for eight years, you would hate it too!” A year later, he introduced the accursed tune by announcing, “And of course, the time comes now for the torturous moment — not for you, but for me.”) Sinatra was hardly the only musician who became associated with a hit he couldn’t stand, but when the Eagles bitch about playing “Hotel California,” well, at least it’s a whole band up there. “My Way” was Sinatra because everybody assumed it was — the lonely man up there on the stage all alone, the cocky bruiser posing as the misunderstood and noble hero.

Of course, having your persona so closely connected to such an oblivious, self-aggrandizing ballad is going to attract a backlash. Just as Sinatra was growing tired of belting “My Way” at every show, younger, edgier rock acts were sneering at this old crooner. Chief among them was Sid Vicious, bassist of the Sex Pistols, a British punk band that never found a sacred cow they didn’t delight in slaughtering. For their film The Great Rock ‘n’ Roll Swindle, Vicious turned “My Way” into a taunt, sending up the faux-dignity of the Sinatra original and laying bare the conceit that the singer was singing the song just to get sympathy from the audience. But why should they sympathize? Why should the audience pay such reverence to the performer? Vicious drove home the absurdity of the one-sided, needy relationship between artist and audience by ending his rendition by shooting people in the stands.

“To me it is tremendous,” Rock ‘n’ Roll Swindle director Julian Temple said at the time. “All the egotism and the individualism and the hypocrisy involved in that song and the audience lapping it up and getting shot to pieces is just wonderful to me.”

Anka was less amused. “Sid Vicious’ version isn’t my favorite,” he wrote in My Way, “and I can’t say honestly that I would listen to it every week, but what he did worked as both a goof and a sincere take on it, which is a pretty amazing accomplishment in and of itself. Sid put himself into the song, and he really did do it his way.”

Everyone from country stars to R&B singers have taken on “My Way.” Elvis did a version, and so did Robbie Williams. When Seth MacFarlane sings “My Way,” you can hear the wink, but Shirley Bassey brings such authority to it that not only does her version sound sincere, it actually feels genuinely melancholy and world-weary — it becomes the weary battle cry of a true survivor. “My Way” can either be a joke or a heartfelt declaration of the importance of sticking to your guns. 

But if you’re one of the people who wants Frank’s rendition to play at your funeral, you’re probably in the latter category.

Those random tweets don’t tell the whole story: “My Way” is frequently the most-requested funeral song in the U.K. (As one funeral director put it, “It’s Frank Sinatra singing about how unique your loved one was. So it’s gonna be tough to top that one.”) Even so, that doesn’t stop cultural commentators from reminding us how much they hate the song, which Joe Queenan once dubbed a “hymn to self-absorption.” It pops up in TV shows and movies, like Mad Men and The Sopranos, but when it does, there’s always a bit of a sting to it — a suggestion that the characters haven’t lived up to the pomposity of Sinatra’s sorrow. And, of course, there’s perhaps the song’s most famous inclusion, which is at the end of Goodfellas, where Vicious’ version is like a snarling rebuke to the corrupt, self-made crooks Martin Scorsese chronicled in his gangster epic.

But no sense of irony or commentary could be found in Trump’s use of “My Way” at his inaugural and then, yesterday, when he flew away. To him, it’s probably just a song about a tremendous guy who did things his way. No doubt, if he ever allows himself to reconcile with the fact that his presidency was an abject failure, he may even take some of Frank’s words to heart:

Yes, there were times, I’m sure you knew
When I bit off more than I could chew
But through it all, when there was doubt
I ate it up and spit it out
I faced it all, and I stood tall
And did it my way

As embodied by Sinatra, who has long symbolized an unapologetic and sometimes retrograde vision of man’s-man masculinity, “My Way” is the ultimate declaration of being unswayed by the winds of societal change — of proudly (and stupidly) sticking to your guns, no matter what. The narrator knows what he knows and doesn’t care what anybody thinks — he considers his stubborn refusal to change or admit defeat a way of projecting strength. Some people very literally are happy to go to their grave espousing that worldview. Donald Trump is definitely one such guy. He thought playing “My Way” yesterday as his presidency shriveled away into irrelevance was a sign of resilience. As always, he was the only one not in on the joke.