James Taylor Embraces Being a Boomer: ‘It Was Such a Phenomenal Musical Generation’

Speaking of being a boomer, are you an AARP member?

I am. It was like 20 years ago, maybe even more, that I did my first interview with AARP. I love AARP. I love my community of older people. When the testosterone and the estrogen diminish, that’s when life gets good.

You’ve performed with incredible people over the years. Does anyone stand out?

There are a couple of people that tragically have moved on now. I’ve worked with Ray Charles. It was just a short while before he died, and it was a major ask to get him into the studio and to work. He invited me to be part of a duets album. We did a song of mine called “Sweet Potato Pie,” which I always wanted to hear him do. Aretha [Franklin] — “Shed A Little Light,” my song for Martin Luther King [Jr.] Day — that was exciting, too. I performed with Yo-Yo Ma and loved working with Yo-Yo, who’s a friend. Paul McCartney played bass on “Carolina in My Mind.” It was a thrill. I’ve had some really incredible opportunities. I’ve had an invitation to sing with Barbra Streisand on an album that she’s making, and we’re going to give that a try. I’ve worked with Vince Gill, although never recorded with him. I’ve recorded with Mark Knopfler. That was so wonderful. Of course, Joni [Mitchell]. I was basically the backing band on that album Blue. And of course, Carole [King]. I played on the same stage as Bob Dylan once. I never actually sang with him. It really goes on and on. Don Henley and Glenn Frey back in the day. Sheryl Crow and I worked together. Taylor Swift played Tanglewood [in Lenox, Mass.] with me one year. Every time I see Stevie [Wonder], he says, “We’ve got to get back together and write another song,” because he and I collaborated on a song called “Don't Be Sad ’Cause Your Sun Is Down.” And I really want to do that. He played harmonica on a song of mine called “Little More Time With You.” Anyway, I’ve worked with some really great people.

Taylor Swift invited James Taylor to perform at the closing of her "Speak Now" tour at New York's Madison Square Garden in 2011.

Larry Busacca/Getty Images

Tell me more about Taylor Swift.

We did a benefit together in New York. And she introduced herself and explained to me that her folks had named her after me and that she had been listening to my music. That was flattering. She invited me to play with her at the close of her first really big tour at Madison Square Garden [in 2011], and she reciprocated by coming to Tanglewood [in 2012] and working with us.

You’ll celebrate 50 years of performing at Tanglewood this summer. Do you have any special memories of your first performance there?

I can’t remember [that night] specifically. They all do tend to blend together. I remember a couple of epic rainstorms that happened over the years there. We can’t take our usual stage setup in there because it’s a very minimal stage, and the acoustic baffling that they’ve put behind the orchestra makes it impossible for us to set up staging and our lights and stuff. It’s bare bones every year, but it’s still the center of my touring universe. It’s my hometown, it’s my home crowd, and the fact that we’ve made it a yearly event that happens on the Fourth of July — everything else falls into place around it.

Do you think about retiring and what that would look like for you?

Yeah, I do, sure. But it would really just feel like slowing down somewhat. I doubt I’ll ever completely walk away from music. Retiring, for me, would mean that I could no longer basically work at a pace that could support a band, and all of the 50 to 75 people that have to travel across the landscape and stay in hotels and take airplanes and rent buses and trucks — all of that. … It’s interesting about getting old. There’s some value to long experience. And for me, there’s amazing value at having a relationship with an audience that spans 50 years. I find myself wanting to basically go back to the same places each year, or every other year. And that’s how I think I’m going to be working in the future — establishing a circuit that I play every other year and have two alternating tours that I do. That’s how I want to focus on doing it as time goes by.

Is there anything you wish you could tell your younger self?

Well, I actually think now that I wouldn’t change anything. And that, in fact, everything leads to everything else. So you wouldn’t want to meddle with it. I would be too tempted to go back and say, “Don’t go away. Don’t leave North Carolina and go to boarding school in Boston, Massachusetts. That’s not gonna make you happy.” I definitely would have, if I could have, skipped a drug addiction. But I was lucky that it didn’t kill me, and recovery was such a gift. Maybe I’d go back and give myself some general and useless advice …. and I’d say, “Don’t listen to anyone who comes back from the future telling you what to do.”