Seven years ago, Kenny Rogers was interviewed by the Guardian. He was about to play Glastonbury, a turn of events by which he seemed utterly perplexed. He suggested the audience might know his music because their parents had played it when they were kids, “which,” he chuckled, “probably counts as child abuse”.

But by then he’d got used to unlikely things happening in his career. There was the gig he played at the Bonnaroo festival in the US the previous year. At an event that had also featured Radiohead, Skrillex, Bon Iver and Kendrick Lamar, Rogers had received some of the best reviews; one critic felt moved to call Rogers’ appearance “the performance of a lifetime”.

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Then there was his popularity in Jamaica. Look on YouTube and you can find shaky cameraphone footage of Kingston truck drivers killing time between deliveries by singing Rogers’ 1979 hit The Coward of the County. The first time he played there, he recalled, it took him four hours to get into the venue, such were the crowds outside. “They knew every word of my songs,” he said. “I think they were all stoned.”

But, for all his bemusement, Rogers seemed seemed to take each unlikely turn in his stride. “Somebody asks me to play, then here I come,” he reasoned. “Nothing stops me.” Maybe he had learned this early on.

Rogers was raised on country music by his mother, a Hank Williams fan, but before his solo career took off, he had variously dabbled in doo-wop; played bass in a jazz trio, the Bobby Doyle Three; done a stretch in the New Christy Minstrels, one of a number of large ensemble folk bands who acted as a kind of finishing school for 60s US rock stars and through whose ranks the Byrds’ Gene Clark, Barry “Eve Of Destruction” McGuire and record producer Jerry Yester also passed; and found success with the First Edition.

This last band couldn’t seem to decide whether they were explorers of psychedelic inner space – their 1967 single Just Dropped In (To See What Condition My Condition Was In) was a favourite of Jimi Hendrix – a country-rock band, a middle-of-the-road bubblegum outfit, a gospel-inspired pop act, or purveyors of funky, Dr John-influenced swamp rock, as suggested by their 1973 medley The Hoodooin’ of Miss Fannie DeBerry/The Ritual. The charitable interpretation was that the First Edition were admirably eclectic, declining to be hemmed in by one genre in the confused, post-Beatles climate of US pop. A more prosaic explanation would be that the First Edition would do pretty much anything they thought might get them a hit.

For a while, it was an approach that worked admirably: they scored a string of international hits and even had their own TV show, Rollin’ On the River. But their career began to wane dramatically. By 1974, Rogers was broke and reduced to promoting guitar lesson albums in a TV commercial; when United Artists signed him as a solo artist in 1975, it was widely thought they were taking a risk on someone whose moment had passed. But the First Edition’s oeuvre contained the seeds of Rogers’ solo success. Ruby Don’t Take Your Love To Town, from 1969, and its follow-up Reuben James were middle-of-the-road country tracks whose musical softness concealed a tough lyrical centre: the first was the story of a paralysed Vietnam veteran imploring his wife not to cuckold him, the second gradually revealed itself to be about an impoverished African-American who’d taken it upon himself to raise a white prostitute’s son after her death.

They were the kind of songs Rogers would turn to over and over again. Behind the Nashville gloss, his first solo hit, Lucille, offered a stark portrayal of a man picking up a woman in a bar, and attempting to forget the sight of her bankrupt husband tearfully pleading with her to return; his signature song, The Gambler, offered the gloomy prediction that “the best you can hope for is to die in your sleep”. The Coward of the County was grimmer still: the song centres around a gang rape. Rogers’ other stock-in-trade was ballads that played on his silver-fox good looks, including a string of duets with the singer Dottie West, brought to an end when she died in a car crash in 1981. They were songs, as he put it, “that say what every man would like to say and every woman would like to hear”.

Together, they made Rogers a star – loosely conceptual, his 1978 The Gambler went platinum five times in the US alone and was subsequently turned into a movie. The success was helped by the fact that Rogers was a charming live performer with a line in very funny between-song patter and by his well-judged and broad-minded choice in material and collaborators that stretched far beyond the usual Nashville songwriters’ pool.

He covered Bob Seger’s We’ve Got Tonight and Billy Preston’s You Are So Beautiful; his hit Lady was one of a number of songs he recorded written by Lionel Richie; and before Bette Davis Eyes made her an adult-oriented rock solo star, he got his fellow former New Christy Minstrel Kim Carnes to co-write an entire album for him, another loosely conceptual work called Gideon. And he was smart enough to avail himself of the services of the Bee Gees when the Gibb brothers switched from performing to writing and producing. The result was 1983’s Eyes That See In the Dark, a brilliant pop album that occasionally hinted at country – as on the track Buried Treasure – but more importantly spawned his peerless collaboration with Dolly Parton, Islands In the Stream, a 2m-selling single that was subsequently voted the greatest country duet of all time by America’s Country Music Television.

In truth, Rogers never came up with an album as good as that again. He subsequently sank into making unmemorable soft rock – umpteen Christmas albums, covers of Labi Siffre’s Something Inside So Strong and Dolly Parton’s I Will Always Love You, an album of religious songs that you could only buy alongside your chicken and dumplings at Cracker Barrel restaurants – with only occasional sparks of inspiration. If it wasn’t up to the standards of his 70s work, 2006’s Water and Bridges was at least interesting, a set of songs about memory and loss that seemed to play on the fact that his voice was ageing.

He didn’t sell records in anything like the quantity he once had, but he remained a huge live draw, always happy to sing the songs audiences wanted to hear: “I’m contractually obliged to sing The Gambler and Islands In the Stream,” he said. “I love it. To come on stage and know I’ve got The Gambler at the end of the show – that’s a weapon.”

They were weapons that invariably worked. For all his doubts about Glastonbury – “I know the acts that play [there],” he mused, “and that just doesn’t sound like me” – he was rapturously received: the response to Islands In the Stream from the Sunday afternoon crowd was such that he was forced to sing it twice. From a vantage point in the crowd, it didn’t look like Kenny Rogers minded doing that one bit.