James Taylor celebrates his 50th anniversary at Tanglewood

“What I do for myself, I make available to other people,” said Taylor, whose silhouette can be seen in front of a large window overlooking October Mountain State Forest.

That approach has worked surprisingly well for Taylor. In the six decades since he began playing open mics on Martha’s Vineyard, he has sold 100 million albums and built a lasting fan base whose emotional connection to his music remains strong. Taylor and his band will be in Tanglewood next Wednesday and Thursday to celebrate the 50th anniversary of the singer’s first performance at the Koussevitzky Music Shed.

This unusual ability to comfort and connect has always been a kind of superpower for Taylor. It’s why he is now so often called upon in moments of joy and grief. Last fall, in the days following the mass murder in Maine that killed 18 people, Taylor, who sang “America the Beautiful” at President Obama’s second inauguration and “You Can Close Your Eyes” at a ceremony marking the 10th anniversary of 9/11, was asked to sing the national anthem before a Lewiston High School football game.

“There’s just something very soothing about James’ voice,” says Carole King, whose 1971 song “You’ve Got a Friend” was a response to Taylor’s lyric: “I’ve been through lonely times when I couldn’t find a friend.”

“James is, above all, authentic,” King said. “The guy you see on stage is the guy he is.”

At 76, Taylor isn’t sure how much longer he’ll keep going, but over a lunch of lobster rolls, kettle chips and coleslaw at his hilltop home in the deep woods of far western Massachusetts, he doesn’t look or sound like someone ready to retire. Yes, he’s lost his hair and moves more deliberately (partly because Butter Bean and Bosun, his two pugs, often snort underfoot), but Taylor, wearing a familiar blue work shirt and Red Sox cap, seems relaxed and content in his role as classic rock’s elder statesman.

“That’s the thing about this phase of life,” he says, getting up from his chair to pull a Tums out of his pocket. “You can feel as good as you did at 55, but two years later you can be on the ground.”

If you’re wondering if he still plays the hits after all these years, the answer is, of course. Because believe it or not, the songs continue to move him. Taylor estimates he’s played about 4,000 concerts — playing “Carolina in My Mind” at every one of them, he says — and yet even now, when he stands (or, recently occasionally, sits) in front of an audience and finger-strums his Olson acoustic guitar, he still feels something.

“It’s a mystery to me why this continues to be so convincing,” he said.

Yet the joy Taylor gets from playing is only one reason he still tours. He has to. Taylor isn’t broke, quite the opposite. He and his wife, Kim, whom he met in the mid-’90s when she worked in the Boston Symphony Orchestra’s publicity department, split their time between Brookline and a big shingled-roofed house and recording studio on 150 acres in the idyllic Berkshire County town of Washington (pop. 454). But in the late ’60s, like so many young songwriters, Taylor naively signed a bad record contract and a disastrous publishing deal that combined to cost him millions in royalties and revenue. “I gave up my publishing house for a sandwich when I was 18,” he said. Now that record sales through streaming have become a thing of the past, the money he makes from performing — Taylor and his band play about 50 shows a year — is important.

The fact that he’s still alive, let alone performing, is actually amazing. For nearly two decades, Taylor abused his mind and his lanky, 6-foot-3 frame with an insatiable opiate addiction that nearly killed him more than once.

“That happened about five times,” he says quietly.

In 1983, a year after the overdose death of his friend John Belushi, Taylor finally managed to get clean – with the help of the late saxophonist Michael Brecker, who sponsored him. He says that surviving the torments of addiction and meeting Kim, with whom he has 23-year-old twin sons Rufus and Henry, “are the best things that ever happened to me.” (Taylor was quick to add that he has “no regrets and feels nothing but gratitude, love and appreciation” for his two ex-wives, Carly Simon, with whom he has a son and daughter, Ben and Sally, and Kathryn Walker.)

Taylor grew up in New Bern, NC, where his father Ike was dean of the University of North Carolina School of Medicine, and he spent summers on the Vineyard. His connection with the Berkshires began with a stay with Austen Riggs in 1969. Taylor had just returned from London, where he had recorded his debut album, “James Taylor” for the Beatles’ Apple Records label. (Paul McCartney plays bass and George Harrison sings backing vocals on “Carolina in My Mind.”) During nine months with Austen Riggs, Taylor wrote most of the songs for “Sweet Baby James,” the 1970 album that made him a star and sold over 3.5 million copies in the U.S. alone. In 1971, two weeks before his 23rd birthday, Taylor was on the cover of Time magazine. Suddenly everyone knew his name.

“My relationship with James goes back further than his relationship with me,” says singer Jackson Browne, a longtime friend who co-headlined a tour with Taylor in 2021. “I was really aware of him because he changed things. James came from folk music, but these weren’t folk songs that he played, they were song Songs.

“They were songs from his experience, his life,” says Browne, “and it was a really amazing development.”

In the early ’70s, Taylor lived for a time in LA’s Laurel Canyon, a storied scene and community filled with talented singer-songwriters, including his then-girlfriend Joni Mitchell, David Crosby, Stephen Stills, Brian Wilson, Judee Sill, Linda Ronstadt and Browne. Eventually, however, he moved back east. Taylor’s mother, Trudy, grew up in Newburyport and instilled a strong affinity for New England in her five children.

For Taylor, the appeal of the Berkshires – his house is about a mile up a mountain road – is their relative isolation. New York feels far away, even when it isn’t, and the small town of Washington, founded in 1777, is mostly virgin forest, giving the place a profound sense of calm. “It’s its own place,” he said.

Taylor is grateful for his success and realizes that his music isn’t for everyone. In a memorable essay titled “James Taylor Sentenced to Death,” rebellious critic Lester Bangs panned the singer’s soothing melodies. Taylor admits that even he cringe at some of his early stuff.

“If it’s ‘Shower the People’ and it feels a little bit sentimental, a little bit embarrassing, well, that’s what came across,” he says of the mid-tempo song, which was a Top 40 hit in 1976. “In that moment, it resonated, and I’m grateful for that.”

Taylor cannot remember his first performance at Tanglewood 50 years ago. Since then, he has performed on the stage of the BSO’s summer home dozens of times, often to sold-out crowds on the Fourth of July. But a review in the Berkshire Eagle of his first performance on July 30, 1974, makes it clear that the audience was enthusiastic: “Many fans in the front row … seemed determined to physically devour (Taylor) rather than listen to his music.”

In photos of the show, which features an opening performance by Ronstadt, Taylor is barefoot, wearing bell-bottoms and a T-shirt. Next week he will wear a collared shirt and a pair of RM Williams boots, accompanied by a cracking eight-piece band that includes Steve Gadd on drums and Michael Landau on guitar. (Taylor’s wife and son Henry usually join him onstage at some point.)

“No matter what room we’re in, it’s a great privilege to play with James,” says Gadd, who has been in the studio for the Steely Dan album “Aja” and Paul Simon’s “50 Ways to Leave Your Lover,” among others. “James is the real James and these days it’s good for people to see the real James.”

Gadd can also confirm that Taylor’s music evokes emotions in people.

“My wife says that all the time,” he said. “When we go shopping together in the supermarket and a James song comes on, she says, ‘Do that every time. It just makes me feel good.'”

Taylor says he still goes through periods of anxiety before a tour begins. He wonders if people will buy tickets or if he’ll be able to conjure that signature sound from his guitar. But once he’s on stage, playing music he describes as “an agnostic’s attempt to make a spiritual connection,” he calms down.

King, who has performed with Taylor countless times over many decades, says he is truly one of a kind.

“When I see James singing in front of a microphone, I think of the joy that emanates from him,” she said. “It’s like the music is playing him.”

You can reach Mark Shanahan at [email protected]. Follow him @MarkAShanahan.