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Up Close with James Taylor

JT REFLECTS ON 50 YEARS AT TANGLEWOOD 


JULY 24

By Anastasia Stanmeyer 


WE ARE SITTING AT THE KITCHEN TABLE IN THE BARN, James Taylor’s recording studio in the Berkshire village of Washington. Bean and Bosun jump excitedly at our feet—and then onto our laps, into our arms, paws on table, bellies waiting to be rubbed. The pugs snort happily into my phone as it records the conversation. I glance at my watch. Nearly two hours have passed, just like that. I apologize for taking much more than the allotted one-hour interview. I imagine James was still jetlagged from his latest string of concerts in Australia and New Zealand, and I didn’t want to overstay my welcome. 

“This is what we’re doing today, talking with you,” he replies, keeping the door open to more questions. This was not just an interview about his 50 years of playing at Tanglewood; it was a deep dive into the thoughts of a person whose songs and stage performances have entertained people for decades. He answers questions that other celebrities would brush aside. On stage and off, James is who he is. You can see his mind at work, his head bowed as he turns over questions before answering, sometimes looking across the table to his wife, whom he lovingly calls “Kimmy.” She gently fills his pauses with more memories, more names and dates. Then James carries on. 


He holds a printout listing of performances that I had requested from his assistant, hands me one, and keeps a copy for himself as a reference every so often when a question arises about the years he’s played at Tanglewood, and those he has performed with. One such person is his close friend Carole King, who offered these thoughts to me in writing: "My most vivid memory of Tanglewood was in July 2010 when James and our fellow musicians—including Yo-Yo Ma at that venue—played for three nights on the outdoor stage of the Koussevitzky Music Shed. I remember how the music lifted all of us above the intense heat and humidity of that summer in the Berkshires. Music + mountains = magic. James, congratulations to you and Tanglewood on your 50th anniversary of playing there!” 

This year's performances are on July 3 and 4, and, as in years past, all proceeds from the July 4 concert benefit Tanglewood. As of this year, James will have made a total of 51 appearances at the Shed. Without a doubt, he continues to be incredibly popular and a sell-out year in and year out at Tanglewood and beyond. The six-time Grammy® winner hopes to replicate Tanglewood’s wildly successful concert tradition in other parts of the country. 

The first time he played at Tanglewood was on July 30, 1974, with Linda Ronstadt. The lawn was half the size it is now, and there were about 15,000 people in attendance. “It was absolutely crazy,” says Dave Winn, who was 15 years old when he attended that concert. “It was wall-to-wall blankets like it is now, everybody was drinking and everybody was smoking, not just cigarettes. It was all young people.” That summer, other popular artists on the Tanglewood stage included Seals and Crofts, England Dan and John Ford Coley, Arlo Guthrie, Pete Seeger, Joni Mitchell, and Tom Scott and The L.A. Express. 


The same excitement is still felt by Dave and countless other people who go to Tanglewood to see James. “I really think people come in that gate, and they drop years and are taken back to an earlier time,” says Winn, who is now associate director of Tanglewood ticketing. 

On this late Saturday afternoon from TheBarn, James talks about his upcoming Tanglewood performances, both sold out long ago. Our conversation turns to his reflections and what he considers the final stretch of his lengthy professional career as a prolific songwriter and musician. Over the course of our talk, we pause for practical reasons: James makes himself another cup of coffee; Kim offers some delectable scones; we (pugs included) look out the window at a surprise guest—a large hedgehog in the lawn. It’s just another day in the Berkshires. 


Anastasia: How is life on the road? Is it challenging at times?


James: In the beginning, it would be routine for me to do five performances, five nights in a row. Now, I like to keep it to two in a row, sometimes three if we're in the same town. How we travel, where we stay, how we get decent food, how we communicate with home—that’s what’s so great about Kimmy and our partnership. She understands what I do, because she has lived in a sort of parallel universe for her working career. She’s traveled a lot; she knows the dynamic and the experience of performing. We share that. It's not like I go away and I'm doing something that's completely detached from my home. Kimmy has an intimate connection with it, and we're partners in all things.


Anastasia: The last time I interviewed you here at your home, nine years ago, you said that even when you two didn't know each other, it was like you were in parallel existences, where at some point you were bound to come together. 


James: It’s the song, “You and I Again.” What are our motivations in this world? Love and death, or love and the denial of death. You wave your flag, and you make as much noise as you can, and you hope that somehow out there, she'll find you again. That's what the song is about, and that's what it felt like to me. 


Anastasia: That’s beautiful. 


James: Yeah, it is. We can't believe our luck. I can't believe my luck. I can’t speak for Kim, but I know she feels the same way.


Anastasia: What is home to you? 


James: What we built together, what we share, the physical context of the Berkshires and the people we know here and the life in Massachusetts and the Northeast. I'm not the first person I’ve heard say this: A lot of people who've traveled a lot in the world for a long period of time have decided that the Berkshires is the place. I don't know why that is. I think it's energy from Boston and from New York. And the finger of the Green Mountains that reaches down into Massachusetts and is the Berkshire Hills. It’s like a route to essential New England, Vermont, New Hampshire, Quebec, and the Adirondacks. That’s what it is geographically, and it has as much history as you can hope for. It also has the cosmopolitan energy of Boston and New York that has always fed it. You feel the cultural roots in dance and the theater and the music that's up here, and the museums. And the people here—we say it over and over again—they’re the people you want to be with.


Anastasia: It must feel really good to be home. 


James Taylor performs for the first time at Tanglewood on July 30, 1974. Heinz Weissenstein, courtesy of the BSO

James: It feels great to come home. The Berkshires isn't a millionaire's ghetto, a bubble for the rich like some resort areas are. It's a real place. I lived in New York, and I would come up about an hour and a half out of town to the northwest corner of Connecticut. I love that area. It's also very much like the Berkshires and sort of has the same vibe. But the compass needle always was pointing to New York. It's too close to New York to be its own place. Maybe when you get to Litchfield, you've escaped. But when you get to Pittsfield, and definitely in Great Barrington, you're far enough away that it's its own place.


Kim: We went on a quest to decide where to live. The boys were two. We looked at France. I took a year off from the BSO. It was after Seiji Ozawa had left and James Levine was coming in, so it was a good time to take a sabbatical after so many years. It was the second time we tried France. We ended up in the French Alps, which was great. Then we decided to go to Sun Valley, Idaho, where James’s manager lived. It was really wonderful, but I couldn’t picture living there. 


Anastasia: How did you finally decide on the Berkshires? 


James: Kim was born in Albany. I was born in Boston. I used to joke with her that she ought to have “Route 90” tattooed on her somewhere. She grew up in Albany and went to school there, and then went to Smith. They spent every summer out at Tanglewood, and she worked for the Boston Symphony [as director of public relations and marketing] and also in Springfield, for a paper there when she was a cub reporter. The thing about France is that if you're in Paris, they’re so prepared to give you a packaged experience. If you're coming from the outside, it's very hard to not get caught in that particular current and—Woosh!—right down the conveyor belt at full speed. We went out to the Alps in that particular foray. We also went up to Quebec and looked around up there a bit. My daughter, Sally, is living in Halifax, Nova Scotia. After Sun Valley, we rented a place in the flats in Beverly Hills, which was great. It’s a real option if you're a performer and in the arts, as we both were. I've been there many times to record and to rehearse. My management was out there. That was a real possibility, but I could never stick in LA either. It was always New England. I had connections here. Before I met Kim, I had spent a year here. It just felt right; we just kept coming back to the Berkshires.


Anastasia: Was that in ’68, ’69, when you were at Austen Riggs? 


James: Yeah, for about six months at Riggs, which was great. My best friend was living in the Berkshires at the time in West Stockbridge. 


Anastasia: How has it become a tradition for you to perform at Tanglewood, July 3rd and 4th?


James: We were just looking at the schedule, and for a couple of decades, I played there in the summer, frequently. It was always part of a summer tour, and it seems to mostly have been in late July, early August. But it wasn’t until ’99 that we played for the Fourth of July. Even then, we only did it for a couple of years. It wasn't really until 2011 that we started doing the Fourth of July regularly. For the past couple of years as a trustee of the BSO, Kim has really pulled back into service there. Not that she ever really lost touch, but she has a bit more time, and the orchestra needed her.


Kim: My term as a trustee is not up yet. It’s three consecutive terms, five years each, so 15 years. When I left the BSO, it’s like I never really left the place. I was made an overseer. After all these years, I didn't think there could be something that's so compelling and a new role. I’m on the Executive Committee now. It happened a year ago. And I’m on the Governance Committee, which is interesting, and the Buildings and Grounds, which I love. And, by the way, James is the first person ever to be a member of a trustee committee who is not a trustee. James had the full vote of the board, so he is on the Buildings and Grounds Committee.


James: Yeah, it’s great. 


Kim: He’s so brilliant—buildings, architecture, landscape. He knows all that.


Anastasia: How do you keep the magic alive every year performing at Tanglewood, James? I don't know any other musicians who come every year, two days in a row to a sellout crowd of 18,000 each night. 


Kim: Is it 18,000? The town put a cap on it. I think it was in 2002, when there was a record-breaking crowd with John Williams. People thought it was a James concert, even though he was a guest at the Boston Pops concert. It was unbelievable. People were just parking anywhere on Cliffwood Street or anywhere in Lenox. Peeing in people’s yards. The selectmen weren’t very pleased.


James: There was already a cap on popular artists, but there was no cap on regular concerts. They just kept selling tickets.

[More than 24,000 tickets were sold for that concert in 2002.]


Anastasia: You have been performing at Tanglewood consistently now. You must love coming back. 


James: People started to think of it as a destination for the Fourth of July. It’s extremely good for me, to have a gig that is kind of like the Rockettes at Radio City Music, or Christmas Pops. I have a few others that feel that way, such as when I go back to North Carolina. I'm also thinking about MGM Music Hall at Fenway on Labor Day; we've done that for a couple of Labor Days now and we're going to do it again this year. Wolf Trap outside of D.C., Ravinia outside of Chicago, Hollywood Bowl. Maybe a week in Las Vegas. As I enter the homestretch of performing in this formula of touring with a big band and playing arenas, I think I have a limited time to continue to do that. I’d like to find a way to keep playing certain places around a certain time of year, the same way we do Fourth of July here at Tanglewood. I'm late getting the idea. I wish I'd been working on it for 10 years already, but I'd like to have that kind of relationship with my audience and the touring that I do. What Billy Joel has done at Madison Square Garden is brilliant. I, too, will look for a place in the New York area. It might be Jones Beach out on Long Island, where I am playing this summer, and where I’ve played so often in the past. Or it might be in town at a smaller theater, like the Beacon. That's sort of my plan now. 


Anastasia: That sounds great. Do you have any special plans for this summer at Tanglewood for your 50th? 


James: We considered a few things, but it's getting a little bit late. I don’t have any. Kim has been asking me that same question.


Anastasia: Sorry to ask you again! 


James: It’s okay. It's a good point. I think the answer is “not yet.” If I do, it's going to be a surprise to everyone.


Kim: Including James!


Anastasia: Looking back at your 50 years at Tanglewood, James, what stands out as a special performance or an incident that happened?


Kim: James was banned one year, did you know that?


James: Well, I wasn’t actually banned; I just wasn't invited back for a long time. My agent, Shelly Schultz, probably felt it out and hit a stone wall. A member of my crew—this wasn't the first time he misbehaved—threw a tantrum. He was told not to drive a truck on the lawn. You’ve asked whether there were specific things that I remember. A couple of them are weather-related, a couple real soakers, with lightning and everything, that stand out. I can't tell you the actual years, but I sure remember them. During one of these particularly soggy visits, the ground was too wet, and Bill Thompson was driving the truck across the lawn. The grounds people, I don't know who the actual person was from Buildings and Grounds—my new home—came tearing out and saying, “Get that truck off the lawn!” It was an old truck with a manual transmission. Bill took the engine up to about 6,000 and popped the clutch in reverse and just tore the Grand Canyon through the lawn. He carved a big trench with the back wheels of this big truck on the lawn just because he was pissed off. It was unforgivable. They didn’t want me back after that. [James scans the sheet of performance dates in front of him.] August 26, 1980, was probably when it happened. I wasn't back until 1990.


Anastasia: What a long stretch without you at Tanglewood! A good friend of mine is a big fan of yours—like many of us are—and every year, she wonders if this is going to be the year where you may not perform at Tanglewood. She can't imagine you ever stopping. Does that ever enter your mind? 


James: Yeah, particularly now, as all of us in the band are aging and looking at a limited amount of time that we can continue to do this. I think about it every year. But I think what will happen is I'll do it until I can't do it anymore, then maybe I'll come back for a special occasion or as part of the Pops, working with Keith Lockhart or in some other form. It won't go on forever. She's right. It is one of those really lucky breaks in my career that I have this association with the BSO and with Tanglewood, that I get to play this gig every year. I'm not gonna let go of Tanglewood lightly. When I stop doing it, it's gonna be because I'm retiring.


Anastasia: Do you recall that first time on stage with Linda Ronstadt, when you were 27?


James: Sometimes I'd open for her and sometimes she'd open for me, depending on where we were. At Tanglewood, she opened for me. I remember …. 

[James stops mid-sentence when Kim turns to him and says, “Did you see that creature, straight out there?” She points to the window, and in the distance, a large groundhog standing in plain view. “Do you see that, Anastasia? Sorry, we’ve been trying to figure out what it was.” James lifts one of the dogs to look out the window just before the groundhog scurries away. “The woodchucks are back. That means the coyotes have moved on. They wiped them out for about seven years.”]


James: Now, back to the first time I played at Tanglewood. The thing I first noticed is that it's a really touchy place to perform amplified music, because it's meant to acoustically make the most of an unamplified orchestra. A singer with a guitar needs a lot more support than a trumpet section and five people playing the bass and a cello section and first and second violins. For the past 20 years, I've been working with a guy named Dave Morgan, who mixes my sound, and before then a guy named John Godenzi, and both of them are excellent engineers. When you drive a room like Tanglewood or Carnegie Hall or Boston Symphony Hall, or any of these places that are meant to hear unamplified classical music, you can really get a disaster. You can walk 10 feet in one direction, and suddenly all you're hearing is bass, or you can walk 20 feet in the next direction, and all you're getting is the drums. The harder you drive a sensitive room like this, the more squirrely it gets. So, really, the first important thing is that our band doesn't play so loud that a guitar and voice can't get above. That comes with experience and maturity, that awareness of what you can do on stage and what you can’t. The other half of it is having a sound mixer who doesn't get insecure and feels he needs to drive it in order to make it exciting. I'm tired of going to concerts where if you don't have ear protection, you're hurting yourself. I've had a couple of times—very rarely, but a couple of times—when I see people wincing in the audience or protecting their ears. I don't want that ever to happen anymore.


Anastasia: Is there any performance that stands out for you at Tanglewood? Besides Linda Ronstadt, you've played with Carole King, John Williams, Yo-Yo Ma, Sheryl Crow, John Travolta.What was it like to share the stage with a young Taylor Swift in 2012? 


James: It was great. The audience was really excited to hear her. She's professional and experienced from a very young age. Yeah, she was really good.


Anastasia: How about Carole King? 


James: The main thing about working with Carole, from the very beginning, it just felt like a musical fit. Like we spoke the same language; like we spoke the same dialect of the same language. I may have gotten some of my harmonic vocabulary from Carole from the songs that she wrote in the ’60s. When Carole and I first worked together, which was on Sweet Baby James in 1970, ’71, it was just like that. She also had been working with my friend Danny Kortchmar, who was an early collaborator, too, and with whom I had that same immediate fit. So that's the main thing about working with Carole is that she and I have come out of the same box and we're cut from the same cloth and I feel at home and supported.


Anastasia: And with Sheryl Crow? 


James: Sheryl is right-sized, and she's a member of the band. I don't know if this is the right place to say this, but I think that being a celebrity is odd. You want it because you want the audience, you want the attention, you want people to be eager to hear what you're putting out. So you want to be known, and you want to have a following. But there are other aspects of it that seem really out of proportion. The whole idea that we evaluate people, it's an inevitable human trait. We analyze and predict and give meaning to and importance to things. But judging people is very tricky. It leads to classism, it leads to elitism, it leads to racism, it leads to all kinds of problems and tribal defensiveness and a plague of ills in humans. So the idea of feeling entitled to being treated like you're exceptional—exceptionalism, the idea of it is one that people that I admire have a problem with. Sheryl is one of those people. She thinks of herself as a member of her band. She does not have an inflated idea of herself. She does have a knack for writing hits. She's a delight to work with, and she has a really wide musical talent. She can play many instruments, she has a great harmonic sense, and, man, can she find a groove and bring you in.


Anastasia: Is there anybody that you would like to share the stage with that you haven't yet at Tanglewood? 


James: Sadly, most of them are gone. I won't dismiss the question, though, completely. Let me think.


Kim: Kenny Crosby would have been great.


James: As I said. I haven't worked with Sting here yet, and he and I have worked together a lot. He’s not a singer who needs a musical director in order to be able to find the right key for him. He doesn't need someone to come in and sing a guide track so that he can find the right part to sing. He’s the real thing. He's a songwriter and a composer. So I love working with Sting. He would be a really good choice.


Kim: And Paul Simon. He lives in Connecticut a lot of the time.

James Taylor with his wife, Kim, and their dog Ting in TheBarn at their home in the Berkshires. PHOTOGRAPH BY JOSH GOLEMAN

Anastasia: They both sound great! I have another question, this time from a co-worker about a lyric that she hears quoted again and again. Her high school drama teacher passed away during Covid, and when they later gathered for his memorial service, this quote was printed on the cards: “The secret of life is enjoying the passage of time.” That’s, of course, from The Secret O’ Life that appeared on your 1977 album, JT. It's a simple yet profound statement. When or how did you come to that conclusion? And do you still feel that way? 


James: It was a song that came very quickly. I was sitting in a patch of sunlight on some steps at a house on Martha's Vineyard that I built largely myself. I was hungover. I had a musical sketch on the guitar, and that lyric just fell from the sky. It's one of those songs where you channel it or receive it, not so much that you generate it. I didn't figure out that philosophical position. As a matter of fact, it's a bit embarrassing. It's easy for me to say, “The secret of life is enjoying the passage of time.” Try enjoying the passage of time when you're on your third round of chemotherapy. Try enjoying the passage of time when you're being imprisoned for being a member of the wrong tribe in a despotic regime. Try enjoying the passage of time when your village is flooded. It's a glib thing to say. But, nonetheless, the thing about it that is wise, is that we only live here, right here and now. And we live on this border of the present, this edge of the present that's moving forward in time. I do still believe it in that way; it is a bit glib for someone like me to say because I've just been unbelievably lucky in this life.


Anastasia: People think that the first time you played in the Berkshires was 50 years ago. But that's not the case, because you played at The Music Inn in 1970. Do you recall anything about The Music Inn? 


James: Yes, definitely. The audience was on a hillside in front of where you performed. The Music Inn had that great lawn that went up quite steeply. An amphitheater needs that. If an amphitheater is too flat, the music just disperses. You need there to be something that comes back. That's what Tanglewood is. The Koussevitzky Shed is great if you don't overdrive it. It’s very contained. It's got those walls around the back that send it right back to you. They're designed so it doesn't come back as a slap-back kind of echo. It just comes back as reverb. Anyway, The Music Inn was a great place to play. And, of course, it had that advantage of being the Berkshires audience, which is very savvy but relaxed. They pick up what you're putting down. That's the thing. You want a smart audience.


On the Tanglewood stage, from top: James Taylor performs with Taylor Swift in 2012; James with Sheryl Crow in 2009; James with his longtime friend and collaborator Carole King in 2010; and James with John Williams and the Boston Pops in 2009.

Anastasia: How has your musicianship evolved through time? Or has it?


James: It has, but slowly. It's always been sort of sui generis to the extent that I'm mostly playing either my own compositions or things that I am covering with my arrangements of them. If you listen to my arrangement of How Sweet It Is, or Handyman or Carole King’s You’ve Got a Friend or Up on the Roof or Every Day by Buddy Holly, any of these songs that I've covered and had success with, they're very different from the originals. A cover should be a new approach to a song. You shouldn't be trying to emulate or repeat somebody else. So I haven't done “James Taylor Goes Country” or “James Taylor Does a Jazz Album.” I've done a Standards album, but the whole point has been my guitar arrangements of those songs. So there haven't been any big steps in my evolution. I started by playing on the guitar as much as I could, taking as big a harmonic bite as I could with the guitar, treating it as sort of like a piano—not like a rhythm-strumming instrument with three chords, but rather trying to do as complicated and complex, as sophisticated musical expression as I could with using just the guitar. Then, as soon as I could, I started adding other musicians. The way that I've evolved as a musician is that I've been able to afford a better and bigger band as time’s gone by. I really use these players. I use their sensibility. It’s called “head arrangements.” I don't dictate what everybody plays. There's a sketch on the guitar that includes everything harmonically that's going to happen. I will write and assign parts for the choral aspect of it because a lot of my music has become very choral with a lot of vocal parts to it. But if I'm using Larry Goldings on piano, I want to know what Larry hears for this song. I want to hear what Mike Landau hears on guitar for this song. I want to hear how Jimmy Johnson plays the song on bass. I want to hear what Steve Gadd does with it rhythmically. I don't want to hire these people and then not use them. I want their talent. So, that's what mostly has happened with my music. And I’ve become better at recording. It took a long time. The first albums I started really feeling good about were my fourth, fifth, sixth albums. Before then, it seemed pretty primitive and a work in progress. That's the other part of me that has grown. I've learned how to make records.

James Taylor connects with fans at Tanglewood in 2014.

Anastasia: And what's the secret to making a good record? 


James: You have an idea of how it should sound, and you get closer and closer to that being what it does sound like. Whereas in the beginning, I had a tune on the guitar, and then what came out once I had played it with a band was, like, “Whoa, where’d that come from?” Sometimes it was great. Sometimes it lost the point entirely.


Anastasia: You won your sixth Grammy® for your album American Standard. Do you have a single favorite composer from the Great American Songbook catalog? 


James: I have a few. Cole Porter is great. Frank Loesser is fabulous. Rodgers and Hammerstein can never be topped. I love Johnny Mercer, Harold Arlen, Yip Harburg. Who am I leaving out, Kimmy? Jerome Kern and the Gershwins, of course. It's just impossible to choose one.


Anastasia: What song of yours would you add to the Great American Songbook?


James: I’d say Mean Old Man. Although it's not the American Songbook, the Brazilian guys—Carlos Jobim, Oscar Castro-Neves, João Gilberto, João Bosco, Ivan Lins, Caetano Veloso, Milton Nascimento—there are so many of those people who are really great. And then there are the Afro Cubans, Eddie Palmieri and the Fania All-Stars, Arsenio Rodríguez. There are people from the Latin world, and I'm sadly lacking the Mexicans and the Colombians and the Argentinians. I know there’s great stuff in there. Cuban salsa and Brazilian bossa nova are just so important to me and had such a strong effect on me. My song On the 4th of July is in that bossa nova samba school. That and my song First of May, Only a Dream in Rio, and also on the last album, Before This World, is the song SnowTime. Those are from a Latin direction that I’m really proud of. 


And then Caroline I See You, You and I Again, Enough to Be on Your Way, God Have Mercy on the Frozen Man, a song on an earlier album called Music that I recorded with Art Garfunkel. There are a number of songs that I feel are my best work that weren't particularly popular. I don't know whether or not they ever will be, if somebody at some point will rediscover them and cover them. I hope so. I try to put them in my performances, but I find more and more that when you're playing to large audiences, they want to hear the songs they know. I don't disagree with them—like Carolina on My Mind, Mexico, Your Smiling Face, How Sweet It Is, You've Got a Friend, Fire and Rain, Don’t Let Me Be Lonely Tonight, Secret of Life. The songs that are on my Greatest Hits albums. Those are worthy, and so much of what makes a performance special is the audience's hearing what resonates with them. I'm more than happy to play anything. There’s nothing that I begrudge or feel resentful about the audience demanding. I never look at it that way. When I come to one of those songs that the audience really wants to hear, it's always a delight. But sometimes I think that there's a stunted development about being so keyed in to wanting the audience's approval. Sometimes I think that I should have outgrown that. Why is it still so compelling to me that I want the audience to be happy, or that I want them to approve me or come away from the performance saying, “That was great. We’d like to do that again sometime”? I don't know why that is, but I definitely have that performer’s mentality that makes the audience's experience extremely important to me.

From top, James performs with his band and his wife, Kim, who is accompanying the other singers at Tanglewood in 2019; James and Yo-Yo Ma at James’s 60th birthday celebration at Tanglewood, July 4, 2008; James and actor John Travolta, also at James’s 60th.

Anastasia: And that’s a negative? 


James: I wonder whether or not it's something I should have outgrown. 


Anastasia: And done what? 


James: Maybe be more secure or less of a people-pleaser. 


Anastasia: But you do throw in songs that aren’t as well-known, and I think the audience really appreciates that. 


James: Well, I'm not sure. You don't want to do too much of your own favorites. Maybe if you announce that as being “Okay, this is going to be deep listening, don't buy the tickets if you want to hear Greatest Hits.” We could try that. We'd have to play small theaters. But we could do that.


Anastasia: Have you thought of resurrecting some of those songs and creating a new album? 


James: You mean give them another shot of trying to do the best possible version of them? Yes, I have. I don't know how I would go about that, because I tried as hard as I could the first time around. Maybe there's a way to arrange them in such a way that they’d have a second chance. I am grateful that I did have such a long period of being important to my audience musically, because it's still going on. I do feel as though, as you get to this end of things, you are playing to people's memories. That’s one of the things that I was talking earlier today about are set lists, making a setlist and why it is so important. We were ordering playing cards that are blank so I could make my setlist of songs on them. It’s a very tactile and analog kind of thing. It resists digitization, the process of writing out a set. I make out cards, and the way the cards feel, and the way that you deal them out and slide them around and rearrange them to make the perfect set for this group for this particular year. Through rehearsals and then over the first couple of performances, they become an evening of theater.


Anastasia: When you're on tour, is the set list the same for every location? 


James: It changes slightly. If you're playing in North Carolina, Carolina on My Mind might want to close the show or first set. I don't play Mexico in Mexico, because I don't play in Mexico. [Laughs] No. Just once. Sweet Baby James and mentioning Stockbridge to Boston is always going to be an important point of the show here, but that's almost always an important song anywhere we play. What we are best at is putting together a set and concentrating on what that means, how that feels as a musical experience, and then working it into an evening of theater that has pacing, that has a sequence, that has a first set and then a second set. The first set is where you will do whatever experimentation or sort of new stuff that you want to offer. The second set should be short, and it should have a lot of that punch to it, even though it'll have a quiet moment in it, as well.


Kim: Tell Anastasia about Streisand.


James: Oh, yeah, we recorded with Barbra Streisand on April 1. She really wanted to do The Secret O’ Life


Kim: She’s doing a duets album.


James: Do you think I ought to touch up any of that vocal that you heard?


Kim: Maybe.


James: Let’s listen to it again.


Kim: Yes. 


Anastasia: Are you working on any other projects?


James: There’s a musical that's still in a very formative stage. The idea is to use my music but not a life story. Carole's done a beautiful one, Neil Diamond has one out. The idea is to work on a way of building a musical that other people can perform, but that uses my music and is somehow dramatically staged. As soon as I know that it's set in stone and that we're going to make a run at it, you will be the first to know. The problem is trying to find songs and to reinterpret them in such a way that they can be handed off to competent musical theater performers and done well and make it work. I’m used to writing for myself and that's it. I’ve written very few songs for other people. Like three. 


Anastasia: We are so very thankful to have you here in the Berkshires. 


James: I feel you got it totally backwards. I am really lucky to be able to call this place home, and also to have a home audience that is so savvy, so sophisticated. Not only are these people in the heart of the Northeast, and all that means in terms of their exposure to world culture and education, but also just specifically the cultural mecca that the Berkshires has become. This is a great place to be at home. I'm sure people are saying that down in Nashville, too. 


[He laughs, rises from his chair, and walks outside with me to my car. As I look back while driving away, I see him running across the lawn, with Bean and Bosun bouncing two steps behind him and Kim smiling beside them.]

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Founded in 2012, Berkshire Magazine is your go-to guide to Western Massachusetts. The high-quality publication explores the arts, homes, happenings, personalities, and attractions with an informed curiosity, exceptional editorial content, and beautiful photography. Berkshire Magazine reaches thousands of readers via subscriptions, newsstand sales, a robust social media following, and in-room at area inns and hotels.

Berkshire Magazine is published by Old Mill Road Media.

Based in East Arlington, VT, Old Mill Road Media is also the publisher of Vermont Magazine, Vermont News Guide, Stratton Magazine, Manchester Life Magazine, and Music in the Berkshires. The award-winning magazines and websites showcase the communities, people and lifestyle of the region.

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