It was based on a French pop song, never made it to No 1 … and yet, thanks to Frank Sinatra, has become a staple at funerals, karaoke bars and everywhere else. Why?

In the late 60s, a young songwriter called David Bowie was asked by his manager to write an English lyric for a French pop song, Comme d’habitude (As Usual), by Claude François. “I turned in the pitifully awful title Even a Fool Learns to Love, which he rejected out of hand, quite rightly, I feel,” Bowie remembered in 1999. “And it passed on to Paul Anka, who did his own English lyric. And he called it, simply and effectively, My Way.”

Anka’s version, sung by Frank Sinatra, entered the UK charts 50 years ago this week. It remained in the Top 100 for 124 weeks, a record-holding 75 of those in the Top 40. One of the world’s most covered and karaoked songs, it is the second most popular pick on Desert Island Discs, and consistently among the top three choices at UK funerals.

The song began life in early 1967 as For Me, a gibberish/English number by the songwriter Jacques Revaux. François, raw from his breakup with France Gall, turned it, with the lyricist Gilles Thibaut, into a sort of proto-Love Will Tear Us Apart: “My hand strokes your hair … you turn your back on me / As usual.” Anka was a former 50s teen idol who had grown up idolising Sinatra and spent time running as a junior member of his Rat Pack. He first heard the song on the radio while holidaying in Mougins that summer and bought the rights to rewrite it, with an English lyric, from Barclay Records. “I just sat on it for a while, letting it manifest and compute,” he remembers.

Facebook Twitter Pinterest Sinatra in 1970, the year after he released My Way. Photograph: AP

Sinatra, about to turn 53, was trying to ride the tumult of cultural change with pop-leaning albums such as Cycles; his film roles eschewed Rat-Pack glitz for world-weary grit. He was in Miami filming Lady in Cement that spring when he met Anka for dinner. “Kid,” Sinatra said, “I’m fed up. I’m going to do one more album, and I’m out of here.” Anka, stricken, returned to New York and worked all night on a valedictory lyric for his French pop song that would trumpet Sinatra’s worth. Sinatra’s response: “That’s kooky, kid. We’re going in.”

Sinatra worked on his delivery and phrasing before entering the studio, getting into the mood of the song in his mind. He nailed it in one phenomenal take. Nonetheless, he had misgivings about what he saw as the brashness of the lyric. “Every time I get up to sing that song, I grit my teeth,” he would say later, “because no matter what the image may seem to be, I hate boastfulness in others. I hate immodesty.”

This is the same Frank Sinatra who, in 1954, had paid for a full-page advertisement in Billboard announcing all the awards he had won and all the movies he was filming, signing off: “Busy, busy, busy – Frank.” And the same Sinatra who had told the Guys and Dolls musical director, Frank Loesser: “We’ll do it my way, or you can fuck off.”

Later, Sinatra would claim My Way “really had nothing to do with my life whatsoever”. Anka, however, felt Sinatra’s experiences helped give the song its power. “Shit happens to everybody every day, whether you’re Frank Sinatra or Joe Blow,” says Anka. “Of course he had regrets – that’s why we sat around and drank every night. You could hear it come out in him, from Ava Gardner, to whoever … but that was the magic of Sinatra: when he sang about it, you believed it. His lucky streak is that he is able to sing about it, convey it and help people along who need it emotionally.”

Sinatra’s performance is hypnotic, masterly in its slow-building defiance, and proud rather than blustery. When the young Bowie heard Costa’s grand arrangement on the radio, he was crestfallen. “So in retaliation,” he said, “I wrote Life on Mars.” A note on the inner sleeve of Hunky Dory reads: “Inspired by Frankie.”

Facebook Twitter Pinterest Shirley Bassey, the first to swap ‘man’ for ‘woman’. Photograph: ITV/Rex

Strangely, for a song that is such a monument, My Way never reached No 1. But it caught the imagination, challenging others to consider what their own way might be.

In 1970, Brook Benton was among the first to reinterpret the song, adding warm, honeyed guitar and a wry little “ha!” after “regrets, I’ve had me a few”. That same year, it was taken on by Vera Lynn, Al Martino, Dorothy Squires and Shirley Bassey, the first to swap “man” for “woman”. Aretha Franklin, in her sensually, softly swaggering southern-soul version, throws the baton to her listeners, undercutting the song’s reputation for arrogance: “Sure, you took some blows / And you did it your way.”

In 1971, Nina Simone’s spry, percussive interpretation brought out a pride more joyous than fearful, and, that year, My Way was also covered by, among others, the jazz saxophonist Gene Ammons, the Japanese drummer Takeshi Inomata and the Indonesian pop outfit the Sitompul Sisters. And, of course, Tom Jones.

In 1972, Paul Anka released his own version, now just one among many, from Glen Campbell’s smooth, expansive take to Joe Frazier’s boxing-themed rewrite in 1971 and Danny La Rue’s drag drama in 1974. And, as the first Elvis Presley single released after his death, My Way took on a quite different kind of defiance. “It takes on many shapes and forms,” says Anka. “It’s not an ego song only … it just depends who the purveyor is.”

The song’s ego was profoundly punctured by Sid Vicious’s cover, recorded as part of The Great Rock ’n’ Roll Swindle in Paris, in April 1978, a few weeks after François accidentally electrocuted himself in the shower. A reluctant Vicious was persuaded to sing it only on the condition that Malcolm McLaren would sign a piece of paper agreeing to relinquish managerial control of him. “My Way was a cliche, a working man’s cry-in-your-beer type thing,” says Julien Temple, who directed The Great Rock ’n’ Roll Swindle. “An old Rat Pack anthem: white, male … just everything Sid was not into.”

Vicious’s recording took place at the Olympia theatre in a spare hour squeezed between the afternoon filming of a variety show featuring an array of old chansonniers (hence the light-entertainment style lit-up staircase in the video). The last performer down the stairs before Vicious was Serge Gainsbourg, who hung around at the back of the hall. “He was getting more and more excited as he watched Sid,” says Temple. “He kept saying it was: ‘classe’, [classy] and clicking his fingers … he got the idea to do the Marseillaise, the reggae version, through hanging out with the Pistols and through seeing Sid.”

Facebook Twitter Pinterest Sid Vicious sings My Way.

While it’s hard to thrill now at such lyrical defacements as “you cunt, I’m not a queer”, Vicious’s cataclysmic version reinvigorated My Way, opening up the field to an even wider range of takes, from the Gipsy Kings’ A Mi Manera via Robbie Williams to Christopher Lee on his 2014 hard-rock covers album, Metal Knight. You don’t even really need to cover the whole thing: Jay-Z sampled Anka’s version for I Did It My Way on The Blueprint 2, and other songs borrow just a line or play on the title, from Calvin Harris’s My Way, Limp Bizkit’s or K-pop group Ateez’s, or Amy Winehouse’s early demo My Own Way (recorded with “Sinatra is God” scrawled on her jeans).

Perhaps the most meta is Sparks’s 1994 track, When Do I Get to Sing My Way, which namechecks Sinatra and Vicious, as its narrator wonders whether he will ever be capable of such grand statements. “My Way was always in the back of my head as one of those epic songs I wished I’d written,” says Sparks’ Ron Mael. “It seemed like a perfect reference for somebody who isn’t in the position to be able to sing that final triumphant song.” His love for the original is sincere and abiding. “I don’t see it being delivered as a statement of arrogance – it seems more like defiance at just being a part of the status quo.”

Everyone has their own interpretation, and each singer brings their own story to the song, from Mantovani to Shane MacGowan. Even Anka has his tweaks. “I add one word at the end, where it goes: ‘And may I say, not in a shy way,’ I go: ‘And may I humbly say.’”

Anka has also written and sung personalised versions about everyone from Sammy Davis Jr to a certain Russian president: “He earns every cheer, yes that’s Vladimir / Vladimir Putin.” Anka’s old acquaintance Donald Trump also had a special version (he thinks it may have been written for one of Trump’s weddings). For his inauguration, Trump wanted a repeat performance. Controversy broke out over whether Anka should do it and whether Sinatra would have approved. “Just remember the first line of the song,” tweeted Sinatra’s daughter Nancy (“And now, the end is near”). The fact that Sinatra performed at Reagan’s inauguration didn’t seem to come up much, but in the end, it was all moot: Anka was in the middle of a custody battle, and the Trumps danced to My Way as performed by a series of unknown singers. “I just chose not to … really get in the fray,” Anka says. “On the other hand, I think that I respect people’s freedoms and what they select to do in life. I had no regrets about not doing it or going there.”

The kerfuffle led to some reflections on the song as “a musical representation of Trump’s approach to the presidency”. David Cameron, too, loves to do it on his karaoke machine after a few glasses of wine, according to a 2012 biography. When Spitting Image marked Thatcher’s resignation, there was only ever going to be one song she could sing. Slobodan Milošević reportedly listened to it while awaiting trial for war crimes. A rightwing anthem, then? Anka demurs. “A lot of Democrats I’ve sung it for … it’s their song, too. Bill Clinton loves it. There’s a host of others.”

Facebook Twitter Pinterest Grimes … bringing the song to a new audience. Photograph: Mark Horton/WireImage

The former German chancellor Gerhard Schröder is one. And at the concert for the fall of the Berlin Wall in November 1989, the East German punk maverick Nina Hagen performed her post-Vicious version, which celebrates freedom and critiques its capitalist incarnation: “And now, all will be well / At your side, there is no bankruptcy … and now money, money, money is worth more than me.” The song is extremely adaptable politically: in a 2001 essay on liberalism, the philosopher Kwame Anthony Appiah related the lyrics to the work of the 19th-century philosopher John Stuart Mill: in the song, he argues, being free to do things your way is a good in itself.

Others question its nobility. David Dale, who performed to several versions of My Way with the drag troupe the Disappointer Sisters for a superb Arena documentary in 1979, says the song mostly makes him think of “drunken slobs singing karaoke at the end of the evening”. As a former karaoke bar owner, he would know. “People who get up and sing it feel that they want the world to know they exist. And, quite honestly, people don’t care.” In 2010, a New York Times article highlighted a number of murders that had taken place in karaoke bars in the Philippines, supposedly because people were singing My Way badly.

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Half a century on, My Way continues to offer new possibilities. Willie Nelson, Miley Cyrus and former Black Veil Brides singer Andy Black have all given it their own spins. In the 2016 animation Sing, the Rat Packy mouse Mike, voiced by the Sinatra obsessive Seth MacFarlane, introduced the song to young ears. More may come to it through Grimes, who recently posted the lyrics on Instagram. It remains to be seen if, and how, they may relate to her forthcoming Miss Anthropocene, “a concept album about the anthropomorphic goddess of climate change”, but it wouldn’t be the song’s most unusual turn.

Because this strange, shifting, accidental monument of song has the power to transcend any one version – even Sinatra himself, despite his version still being the one I come back to. Perhaps it owes its longevity to that. I wouldn’t bet against it surviving another 50 years, as new generations discover it and decide to do it their way.