The following is from LIFE’s new special edition on James Taylor, available online and at retail outlers:

He could have been any American college student visiting London in 1968, except that James Taylor wasn’t in college. He did have a guitar and he busked in the street for change, which he used to visit a record-your-own-record booth in Soho. There, he spent £8 for 45 minutes of time to record a demo of a song he had written, the one he considered his best. Taylor was 20 years old. The song was called “Something in the Way She Moves.”

In London, he crashed at the flat of a friend named Albie Scott. Another friend—his sometime bandmate Danny (Kootch) Kortchmar—had given Taylor the phone number for Peter Asher, the head of A&R for the Beatles’ new label, Apple Records. Asher, a former pop star as half of the duo Peter and Gordon, had had a number-one hit, “A World Without Love,” written by Paul McCartney. Now he was charged with finding new talent to ride the magnificent silk coattails of the post–Sgt. Pepper Fab Four. The exec agreed to meet with Taylor and listened to a few of his tunes. Then Asher “suggested I come by the office later in the week and play my songs to whichever Beatle was around that day,” Taylor recalled later in his audio memoir, Break Shot, named for the instant in a game of pool when the racked-and-ordered billiard balls are struck and violently scattered to an unknown fate.

In the five-plus decades since his big break, Taylor has been one of the most successful recording artists in the world, and Asher his sometime producer and manager. Fact has calcified into legend over time, but Asher often has said that he stepped into the Beatles’ offices on Baker Street with Taylor on that incredible day in 1968 and shouted: “Is there a Beatle in the house?” As if from a magic lamp, the genies McCartney and George Harrison materialized from behind closed doors, and Taylor was invited to play live with these gods who had the power to grant wishes. As the world’s most popular entertainers, the Beatles, and Apple, had been inundated with demo tapes, most of them appalling. McCartney and Harrison listened to Taylor’s music anyway. “For once, it was someone really great,” McCartney said years later, while inducting Taylor into the Rock & Roll Hall of Fame. “It was this kind of haunting guy who could really play the guitar and really sing beautifully.”

So beautifully, in fact, that Harrison would use the first line of Taylor’s demo for a song of his own: “Something in the way she moves,” Taylor sang to the Beatle that day, to which Harrison would later add “attracts me like no other lover . . .” “Something in the Way She Moves” would become a slow-burning time-release hit for Taylor, and “Something” an instant classic for the Beatles, covered by everyone from Elvis Presley to Frank Sinatra. But it started with Taylor in that record-your-own-record booth in Soho. As he sat in the Apple offices with two of the Beatles, he contemplated his change in circumstances and realized, as he would say many years later, “This is when my life passed through the looking glass.”

That was young James Taylor—long and thin as a switchblade, with a curtain of black hair drawn open on a face that launched a million album covers: blue eyes, blue denim shirt, the brooding gaze of the earnest singer-songwriter familiar from his breakthrough sophomore album, Sweet Baby James. Today, the six-foot-three Taylor remains as tall and lean as he was in his Mud Slide Slim persona of the early ’70s. He’s bald, the legacy of his father, who was shaving his head in the 1950s when only the actor Yul Brynner did so. Taylor smiles often now, a grandfatherly figure in his flat cap. Indeed, Taylor is a grandfather. He is at once a Northerner and a Southerner—“a Northern baby and a Southern child,” as Carly Simon sang when she was his wife.

James Taylor was born in New England but raised in North Carolina, then returned to New England equal parts Beacon Hill and Chapel Hill, the son of a “Down East Yankee,” as his mother described herself, and a Down South doctor. “James Taylor,” as Time magazine noted in its cover story in 1971, “managed to grow up in two of the most beautiful places in America.” As such, Taylor sings equally in thrall to the country roads of Carolina and the Massachusetts Turnpike between Stockbridge and Boston. Like Johnny Cash, he’s been everywhere, man. “The coldest I ever played was 19 degrees and the earth was like iron,” he says. “And the hottest was probably—not counting the lights—100 degrees in Tucson, Arizona.” His star was launched in England but he may be the quintessential American artist, bridging North and South, rural and urban, hot and cold, fire and rain.

He has been both addict and recovering addict, a mellow folk-rock singer-songwriter whose nearly two decades of opiate addiction would seem more common in hard rock, blues, and jazzmen than in the elder statesman of mellow rock that he is now. These two sides of him may not be unrelated. In a famous essay called “James Taylor Marked for Death,” the rock critic Lester Bangs dismissed Taylor and his mellow, “down-a-Carolina-path” songs of introspection as anathema to rock and roll. Taylor has never read the Bangs piece but replied, in 2015 to Billboard, with his trademark self-deprecation. “I’m an opiate addict,” Taylor said. “Mellow and smooth is fine for me.”

That introspection and addiction have been two sides of the same coin. Taylor was hospitalized for mental health issues as a young man but has also come as close as any songwriter to divulging the meaning of existence. “The secret of life is enjoying the passage of time,” he sang, while acknowledging in interviews the hubris of any man who claims to know what it’s all about. And yet, he isn’t wrong, is he? Taylor wrote “Secret o’ Life” in 10 minutes outside a house he was having built on Martha’s Vineyard, a house that was the fruit of having sold more than 100 million albums worldwide. Taylor has also won six Grammys and was inducted into the Rock & Roll Hall of Fame in 2000, presented by McCartney. J.T. has also worked with and inspired other famous artists of his generation, having been a muse at various times to three phenomenal songwriters: Carly Simon, Carole King, and Joni Mitchell.

His effect on later generations of musicians and music fans is enduring. It wasn’t until 2015, somehow, that James Taylor had his first number-one album, Before This World. It narrowly eclipsed the number-two album, 1989 by Taylor Swift, the pop icon who had a favorite song in chorus, she told her mother one day: “It’s called ‘Fire and Rain’ by a guy named James Taylor.” “It’s really funny that you say that,” Andrea Swift told her fifth-grade daughter, “because you’re kind of named after him.”

Swift is hardly the only one. Garth Brooks named his daughter Taylor for the same reason. The young English singer-songwriter James Taylor-Watts, who performs as James TW, was also named after his parents’ favorite musician. “You just call out my name,” Taylor sang in 1971 on “You’ve Got a Friend,” and now, more than 50 years later, people all over the world do just that when calling their own children and grandchildren. When Barack Obama presented Taylor with the Presidential Medal of Freedom, the nation’s highest civilian honor, in 2015, the White House cited among many other achievements the singer’s continued relevance, his appeal to all ages, stating: “Each generation that grows to know James Taylor’s music will continue to be moved by his timelessness and enduring beauty.”

I can attest to that. When my oldest daughter, Siobhan, was a child, she fell asleep every night to Taylor’s Greatest Hits CD. I was required to stay in the room until the end of the fourth song, the lullaby “Sweet Baby James,” written 40 years earlier for Taylor’s newborn nephew and namesake. In 2015, when she was 10 years old, Siobhan and I went to see Taylor perform live at an amphitheater in Hartford. Halfway through that show, Taylor announced there would be a short intermission. He didn’t care for intermissions himself, he said, but the venue or promoter insisted on it so that fans could use the bathroom and buy concessions. “I’ll just stand backstage,” he said, “looking at the clock.”

But he didn’t. Instead, Taylor spent the intermission sitting on the edge of the stage, haloed by the footlights, chatting with fans and posing for pictures. Nudged forward by me, Siobhan took my phone, snaked her way to the front row, and asked the artist for a selfie. But in the lights and the clamor—his working life of the last half century—Taylor misheard her request. Instead of posing for a picture in front of the iPhone that she’d held aloft, he took the iPhone out of her trembling hands and signed the back of the case, boldly, legibly, with a black Sharpie.

That case remains on a shelf in her former bedroom, the signature slowly fading into oblivion, the way “Mexico” fades out at the end on that Greatest Hits CD that Siobhan, now in college, fell asleep to every night in grade school. By “Mexico,” the 10th song, she was always fast asleep. And so it was that night at the concert. Lulled by Taylor’s familiar voice, she began to nod off in the amphitheater, her head leaning on my shoulder, her hands clutching the signed phone case, while I sat contentedly beneath the summer night sky thinking of something Taylor had sung earlier in the evening: The secret of life is enjoying the passage of time.

Here are a selection of photos from LIFE’s new special issue on James Taylor:

Cover image by Eleanor Bentall/Camera Press/Redux

James Taylor performed for the BBC in London, 1970.

Michael Putland/Hulton/Getty

James Taylor performed at the Mariposa Folk Festival in Ontario, 1970.

Michael Ochs Archives/Getty

James Taylor with Carole King and producer Lou Adler during the recording sessions for King’s album Tapestry, 1971.

Jim McCrary/Redferns/Getty

James Taylor with his cat Pudding in Los Angeles, 1972.

Peter Asher/Michael Ochs Archives/Getty

James Taylor at a benefit for presidential candidate George McGovern (to the right of Taylor) in 1971; others on the stage are (from left) Barbra Streisand, Quincy Jones, Eleanor McGovern (George’s wife), and Carole King.

PL Gould/Images Press/Getty

James Taylor with Carly Simon in New York’s Central Park during a record company event, 1977.

Richard E. Aaron/Redferns/Getty

James Taylor, the musical guest on a 1979 episode of Saturday Night Live, joined in a sketch with that week’s host, Michael Palin.

Alan Singer/NBCU Photo Bank/Getty

Singer James Taylor, second from right, and members of the Taylor family share a laugh, prior to their concert at New York’s South Street Seaport Museum to benefit the Museum’s Save Our Ships Fund, 1981.

Photo by Richard Drew/AP/Shutterstock

James Taylor and Taylor Swift performed onstage during her “Speak Now” tour at Madison Square Garden on November 22, 2011 in New York City

James Taylor and Ringo Starr (right) performed in 2018 at a benefit for VetsAid in Tacoma, Washington.

Mat Hayward/Getty

James Taylor, 1997.

Brooks Kraft LLC/Sygma/Getty