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

Singer-songwriter acknowledges longtime fan base, celebrates 50 years of shows at his hometown venue


spinner image James Taylor wearing jean jacket and hat with number nine on it, against yellow ombre background
AARP (Norman Seeff)

Singer-songwriter James Taylor, 76, feels a special connection with his fans from the boomer generation. “We really did think we were changing the world,” he says. He also shares a special connection with a much younger musical superstar: Taylor Swift. James recounts that the two met more than a decade ago, and Swift revealed that she was named after him. He shares with AARP more about the musical legends he’s worked with, the advice Tony Bennett gave him and how he’s preparing for his summer tour, which kicks off May 29 at L.A.’s Hollywood Bowl.

This interview has been edited for length and clarity.

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As you gear up for a tour, do you have to do anything to get into shape?

In getting sober [in 1983], I also found that in order to get my nervous system back, to get comfortable in my own skin again, I had to get really fit. I went into a kind of athletic mode for about 20 years, from the age of 35 to 55. And then my second family of kids was born [in 2001] — twins Rufus and Henry — and I started backing off the physical activity a little bit. But that sort of late push set me up really well. I just feel as though I’m physically up to it. There’s a little bit of use it or lose it. I remember Tony Bennett told me once, “You’ve got to do your vocal exercises every day. You have to do that. If you skip it for one day, you’ll feel it. If you skip it for two days, people in the band will begin to feel it. If you skip it for three days, people in the audience will begin to notice. And if you skip it for four days, the critics will notice it.”

So are you doing daily vocal exercises?

I do, especially in the two weeks leading up to rehearsals, I do a couple of hours every day of vocalizing and trying to bring it back up. And I start singing through the set list that we made for the summer. About a month out, I start working on it. … It’s important to have a couple of gigs placed here and there that will pull [the band] back together and just be stepping stones that’ll get us through that off period. At this point, it’s a very familiar process — getting ready to go out on the road — and you do learn to do it. In the beginning, it beats you up pretty bad, and you overbook yourself, but now we know what we’re doing a bit.

Your fans seem to feel very loyal and connected to you. Why do you think that is?

There’s something about the baby boom generation — I was born in ’48, so I’m pretty much in the middle of it. It was such a phenomenal musical generation when that big lump of population got to be about 20 years old, and it was using FM radio to define itself and communicate. And we really did think we were changing the world. And although we didn’t change it as much as we wanted, or as we thought, it was culturally a massive thing, the baby boom bulge. I still feel as though it’s sort of the dominant generation. It still feels like an entity to me.

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.

spinner image James Taylor and Taylor Swift sitting on couch playing guitar; microphone in front of each of them
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.”

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