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Shakedown Beat chronicles WAMC Berkshire Bureau Chief Josh Landes’ musical adventures in the northeast.

‘Creativity... is making yourself uncomfortable, trying to find a way out, being surprised’: The Dream Syndicate’s Steve Wynn checks in before North Adams gig

Steve Wynn.
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Steve Wynn.

Steve Wynn is a living legend of the American indie rock scene.

Famed for both snarling, blown-out guitar explorations with bands like The Dream Syndicate and his more intimate solo singer-songwriter material, the Los Angeles-born troubadour has trod the globe playing for audiences and cutting records for close to half a century. On May 16, Wynn - no stranger to North Adams, Massachusetts - will bring his current tour that combines excerpts from his recent memoir with a musical journey through his life to Belltower Records. Before the concert, Wynn spoke with WAMC's Josh Landes about the importance of being surprised, the beauty and chaos of baseball, and how Miles Davis and krautrock blew his mind and helped shape his sound.

WAMC: Steve, you've had a long and absolutely fascinating career in music. You've managed to be a part of a few really interesting moments in musical history. But I'm interested - right now in 2026, when you think about the trajectory of your career and where you find yourself right now, how do you describe the current zone for the kind of music you're making and performing?

WYNN: Well, I mean, at this point, the current zone for me is just my own personal zone. I don't feel like- I mean, I've been doing this now, bless my lucky stars, for 44 years professionally as a touring and recording musician, which is just great. So I mean, kind of at this point, I don't think that much about where things are in some perceived music business or music world or trends or scenes. I just make my own music, and I'm grateful there are people out there who want to hear
it. 

There's so many cool things you've been involved in that I'm so excited to bother you about. 

Bother away, bother away!

I’m going to bother you, brother. You recorded one of your more acclaimed records in Ljubljana, in Slovenia. I've actually had the pleasure of spending a fair amount of time in Ljubljana, it is such a magical city. Can you tell me a little bit about that? I mean, what kind of environment was that? It's this picturesque river city in beautiful Slovenia. It's very special and maybe slightly off the beaten path. What drew you to that? And what was it like? 

It is a gorgeous city. I love it there, and I've been there, luckily enough, many times. I just played there with The Dream Syndicate, my band. We played in February and had a great couple of days there. It's a gorgeous city, of course, and very inspiring. But the reason I was there in particular was a gentleman named Chris Eckman of the band The Walkabouts, originally from Seattle. He and I have been friends for a long time, and he's not only a musician and writer, but also a really good producer, and we had talked for a long time about doing a record together. I like the way he would mix singer-songwriter material with strings and more elaborate, lush arrangements, and I wanted to see what he could add to my music. But we're both pretty active touring and recording musicians. We both are pretty busy, and it took us about 10 years to finally make it happen, during which time he had fallen in love with a woman from Slovenia and moved there and got married and was living there. So I said, well, you know what? Rather than trying to meet somewhere in the States or anything like that, I'll come to Slovenia, spend a month over there, we can finish writing together, do pre-production and record it while I'm there. And it was great. I kind of went over there to Ljubljana with songs either, a handful of songs finished, a handful of songs halfway finished, just kind of in various disarray. And I figured the vibe there, the look of the city, the feel, the jet lag, the excitement of being somewhere else would help me take the songs and the recording to the finish line, and it did. I really hear, and maybe you do as well, since you've been there, I really hear the city of Ljubljana on the recordings we did. 

Punching Holes in the Sky

“Crossing Dragon Bridge” – I mean for the record, I think you're something of a genius at titling things, from The Dream Syndicate to “Crossing Dragon Bridge,” which sounds like an epic non sequitur, but in fact, there is a Dragon Bridge, and it's depicted on the cover of the album. 

Yes, yes, I'm sure you crossed it a few times. It's really essential to the city and a very beautiful bridge. Yeah, sometimes you get lucky with titles. Sometimes you don't. There have been titles for records I've made over the years where it just came to me easily and quickly. I went, yeah, that couldn't be anything different. And there's other titles where you spend weeks and weeks thinking, what am I going to call this thing? And, I've got a few that I love less than others, but that's just, you know, the nature of the beast.

I think what's so cool about your music and The Dream Syndicate, your solo work, etc. – it's this fascinating crossroads between this minimalism and fascination with long-form improvisation, and also writing real rock and pop songs that have a lot of structure to them, and I'm interested in how you conceptualize bridging that gap. I mean, you've talked about being inspired by La Monte Young, and you're also playing this beautiful pop music simultaneously. It sort of seems like quite an accomplishment to explore this more experimental edge of music, but also have it really tied to a very firm foundation in songwriting. 

I've always liked that clash of classic songwriting, Tin Pan Alley, straight through to Lennon-McCartney, straight through to all the singer-songwriters of the 70s. I've always liked a good, well-written song, but I've always liked noise and distortion and feedback and that kind of thing. And if I had to say what my roots are that steered me towards making records, it was punk rock. Hearing punk rock in the late 70s completely blew my mind and made me realize that things that are more raw and passionate and broken and maybe not virtuosic execution can bring even a stronger impact to the listener. So I kind of have always sort of done that. I try to write a good song that works on an acoustic guitar, but also can withstand a little tension here and there. And you mentioned La Monte Young, and La Monte Young was a big influence on Lou Reed and actually a member of the original Dream Syndicate, the pre-Velvets band that he had with them, with Tony Conrad and John Cale – a band we did not know about when we started our band, incidentally. But the Velvets and Lou Reed, they did that before anybody else. There's a lot of things you can credit the Velvet Underground with – great songs, all of that – but they were really kind of the first band that said, we're going to take a beautiful song or a great song that would would normally be just a normal, middle-of-the-road rock song, and we're gonna mess it up beyond belief and see what happens. And that's just something that influenced me and so many other bands.

I want to ask you about the 2020 Dream Syndicate album “The Universe Inside.” I'm a huge fan of sprawling songs, and you kick off the album with a 20-and-a-half-minute-long track, “The Regulator.” I sincerely doubt it was meant to be a provocation, but obviously, you're definitely kicking the door open by starting an album in 2020 with an over-20-minute-long opening track. Tell us about the decision making and thoughts there. It's a phenomenal track. 

Thank you. It's actually one of my favorite records I’ve ever done. I think if you ask any member of the band their favorite record by The Dream Syndicate, and we'd all say that one. It's such a - I don't know. It's just a record I like a lot. Funny thing is, you mentioned 2020. Our bad luck, it came out when the pandemic started, which meant we couldn't tour behind it, which maybe was a blessing, because I think all of a sudden, a record with a 20-minute opener and an hour-plus record which is five songs came out at a time where people had a lot of time on their hands. So I think there was maybe a little more openness to the sprawl of that record during a time where people had room in their lives for some sprawl. It's a record I'm really proud of. It came out of mostly improvisation, a jam session the band did in the studio well after midnight while we were making another completely different record. And I just really liked this particular jam. Jams are often just entertaining to those who are doing it and not to anybody else. But in this case, I thought we kind of latched on to something in our half-sleep state. And I spent a good portion of time taking that jam and slicing and dicing and making it fit into songs, and it just came out great.

The Dream Syndicate - "The Regulator"

I’m interested in your thoughts - Being a guy who's had a long career in music, there's this soul-crushing tendency to reduce things to historical periods and genres and XYZ. Part of what makes your career so interesting is that, again, you've darted in and out of these different sectors. You went to high school with the Germs, you're making 20-minute-long psychedelic jams to kick off albums in 2020, and then, on the other hand, you have more delicate, tender singer-songwriter stuff. How do you stay creative and inspired despite this societal crunch to reduce things to hashtags or genres or eras? 

I just do what I do, really, and I don't think about it too much. I mean, I do listen to a lot of music, old and new. I read a lot, and just try to take in as much inspiration as I can. But when I was younger, I mean - For example, the first record I made, “The Days of Wine and Roses” with The Dream Syndicate, I knew what I was trying to do. I could take each song of that record and say, well, I was trying to do a song that sounded like this band or that band, checked all these boxes that were important to me. It's what you do when you're starting out. But to be honest, at this point, when I write a record or write new songs for a record or go in the studio, I really don't think about what it's going to mean, who it's going to connect with, what genre. I just make the music that I want to make that's in my head. Now, when I listen back to it later on, I'll say, yep, that's the record I was listening to, I was listening to this band quite a bit, or thinking about that place quite a bit. But really, it's more just following whatever direction is in my head at that moment and seeing it through. So, I think it's kind of natural, you know? If I listen to “The Universe Inside,” for example, it was just a jam. We didn't say, let's do this kind of a jam, or let's play as though we are this band or that band, and this here in that studio. We just played everything we never listened to, everything we'd ever done, everything we'd ever thought about, everything we'd ever watched. It fit into the DNA of what we were spitting out, of course, but it wasn't by design. Now I can listen back to that record and say, oh, yeah, obviously our love of early 70s Miles Davis influenced that record, or our love of Can or NEU! or what have you, that fit into that. But you don't think about it when you're doing it. You trust your instinct. When you don't trust your instinct is when you start to go south.

Okay, I've got two follow-ups to that. The first is, gun to head, favorite Miles Davis record?

That's easy, and I like so many, but gun to head, I would say the “Jack Johnson” record he did, the two-song record he did with John McLaughlin and that great band. I play that so often, but I'm also a big fan of “On The Corner” and all the records the great quintet made in the mid 60s, and “In A Silent Way.” And I can just keep going from there, of course – “Kind Of Blue” – but really, push comes to shove, the “Jack Johnson” record is great. 

Second follow-up: Is “Hallogallo” just the best song ever?

You know, it's so funny because – and you're mentioning the NEU! track – when we started The Dream Syndicate in ’81, I had no idea who NEU! was. I was a big music fan, but back in 1981, ‘82 you couldn't find records by NEU! anywhere. I would say in the States, but really anywhere. I remember I became a fan of the band because our drummer, Dennis Duck, who is a little bit older and was hip to all that krautrock stuff - Faust, NEU!, Can. And he turned me on to it, and I went, this is just great. I remember going over to Germany in the mid-to-late 80s to a record store trying to hunt down – of course, this was way before streaming, so you couldn't always find the music you wanted to hear, it was like, if you want to hear it, you have to track it down. And I went to a record store in Germany, said, do you have any records by NEU!? And they looked at me like I was insane. I said, NEU!? And I thought maybe I was pronouncing it wrong, who knows what I said, so I said, N-E-U? And he said, no idea. So that just shows you how obscure that band was at that time. But luckily enough, I got, as is the case when you're a lucky music fan, somebody older, somebody who's been around a little bit longer, turns you on to something great. And I will say that NEU! and that track, and everything they did, and the drumming of Klaus Dinger has such an impact on so many things I've done.

Turning to my favorite intersection, music and baseball, you are a member of the Baseball Project. I could ask you all day about more discrete baseball questions. We'll start with a basic one, who are you a fan of? Who do you root for? 

Well, this is a dangerous question, given that I'm heading up to a show in Massachusetts. I'm almost afraid to say, but I'm a Yankees fan. Please still come to the show and don't hold that against me if you're a fan of the other team to the east. 

I will do my best, sir. So, secondly, when it came to translating the appeal of baseball to this group - there's so many angles to approach it from. It's a game that is all about tension, and each individual action fitting into this larger chess match between two organizations. It's a sport where chaos reigns supreme, and almost every decision can trigger a domino effect that is almost completely unpredictable. What went into this process of talking about baseball in a musical setting? 

Well, you phrase it so well. You really made a great case for the beauty of baseball, and you're right. And not only does chaos reign supreme in all the decisions involved, but baseball is also a game slow enough and outside of the realm of time that it gives you the chance to think about those decisions and that chaos and the history and everything. It's a real internal thinking person's game, and that's why I think it lends itself to songs. I mean, I'm sure you could write songs about football, American or European, or you could write songs about basketball or whatever, easily. But baseball, really, among other things, baseball is a game of the individual. You could be a great basketball player, but if you're surrounded by a lousy team, it'll be hard for you to shine - not impossible, but hard. Baseball, the basic foundation of the game, is the pitcher and the hitter, man on man, one person against another. That brings in all kinds of great history. So I think with the Baseball Project, you know, we really try to not just sing about this statistic or that incident in baseball – which we do as well – but I think we try to use baseball as a metaphor for all the same questions in life that you address in songwriting anyway. In some ways, I think the Baseball Project is a more emotional and very personal band and style of writing than in any of our other bands, and that's a lot of fun. I also can't believe that we've been a band for almost 20 years. I think we started it just as a lark. I mean, Scott McCaughey – my collaborator in the band, of course, Scott of the Young Fresh Fellows and The Minus 5 – Scott and I just on whim, said, let's write songs about baseball. We've always wanted to do that, and we can get Peter Buck and my wife Linda on drums, and we'll go and record them, see what happens. And here we are still touring. 

Have you actually heard from any major league players past or present about the Baseball Project? 

We've had a few. In fact, the current general manager of the Red Sox, Craig Breslow, was an early fan and had us perform at one of his charity events. And we stayed in touch over the years, and there’s been a couple others here and there. But the reality is, I think most players today aren't necessarily big rock fans. Some of the older ones were. Jack McDowell, who we wrote a song about, Jack McDowell, being the premier pitcher of the 90s, is a big fan of the band, has come to see us play, and he's also a touring musician in his own right, so he gets what we're doing. And there have been a few - mostly the people who kind of get into the band in the baseball world are front office people, sports journalists, baseball announcers. We have a few announcers out there who love the band, not the jocks, but the analysts, the ones who do the same thing in their own field that we do with our songs.

The Baseball Project - Full Performance (Live on KEXP)

I want to turn to your most recent release, which is very cool. It’s “I Wouldn't Say It If It Wasn't True--Live in Rome.” This is you exploring your memoir through song on the road. Something that I thought was so interesting is that in your write up about this recording, you talk about taking the stage in Oxford, over in the U.K., and this walk you went on through the city before the show. And the sense of place pervades so much of your work. The record that was released in tandem with that, “Make It Right,” talks about your journey from Santa Monica to New York, and in so many words. Can you tell me a little bit about how much place and space in the real world influences your creativity?

Quite a bit. I mean, like we were talking about earlier with Ljubljana, I've done plenty of records at home or close to home or in familiar environments, but I really do like placing myself in a situation, and seeing what comes, what happens, being excited. I think a lot of creativity, and especially if you've done it for a long time, is making yourself uncomfortable and trying to find a way out, being surprised. I think, not just with music or arts in general, but I think we're all kind of excited when we have a skill or a passion for something and we’re faced with a challenge, whether it's building a house or working on your car or being a baseball player or whatever, saying, well, I'm really experienced, and I think pretty good at what I do, and I'm faced with this thing here that I don't quite know how to solve. Let me use what I've got to work it out. And then when you do, it's very satisfying. It's why I love playing live so much. I love playing live and touring because every night, you're on stage in a different room with different sound, with different circumstances involved, and it's up to you to be open enough but also focused enough to figure it out. And so that's, that's nice. I mean, even as a songwriter, I find I write fewer songs now with a guitar in my hand and pen close by. It more comes from just being faced with a challenge, a collaboration, being outside or someplace I haven't seen before, and taking it all in and spitting it back out again. So I think that there's a lot of that. Now, you brought up the “Live In Rome” thing - my book, “I Wouldn't Say It If It Wasn't True,” came out, God, a year and a half ago now, almost two years ago, and since it came out, I've been touring relentlessly around the world, putting together the show that's kind of a mixture of some readings from the book, stories, and songs to go with all that, which is kind of the show I'll be doing on this tour as well. And the “Live In Rome” CD is a night along the tour where I did that. The Oxford thing you're talking about - yeah, that was wild. It was the first show where I was going to present the book in concert, and I knew I wanted to do that kind of a show, and I set aside a few sections to read and a few songs I wanted to play to go with it, kind of a rough outline. But I didn't know what the show would resemble. And like you mentioned and I mentioned in the liner notes for the record, I had about two hours between the sound check and the gig in Oxford, U.K., and I went walking and let what I was seeing influence what I wanted to say. And I went back in the club kind of invigorated, and did the show pretty impromptu, and liked the way it went, and the show I'll be doing on this tour is not that different from the one I did that night. 

Now, in your days of traipsing across the musical scene, both in America and far beyond, what are some of your favorite venues to play? Is there one that comes to mind as like, that was a really special spot? 

God, so many. I mean, where to even start. I've been lucky enough to have been around long enough to have played some of the classic venues – CBGBs, or the Marquee in London, or the Markthalle in Hamburg, all these places where so many bands have played. A lot of those venues are gone now, a lot of those great classic venues, but one still around is the Troubadour in LA. And you know, I grew up in LA, and the importance, the historical, musical importance of the Troubadour is still there when you walk in the room. And I'm fortunate enough, I've been able to play there a half-dozen times. And I just, I love it. I love playing there, and I'm not going to say it's because it's the best room or the best sound or the stage, just because of the history.

There's often a sense of pessimism that pervades culture in 2026, for some reasons that I understand, and others I think might be hyperbolic and spurred on by our media environment. But how do you look at the future right now in 2026? You certainly sound so full of life and so enthusiastic, I can infer you're certainly not down in the dumps right now. But generally speaking, both in the music world and beyond, how are you looking ahead right now?

I'm just taking it day to day. There's so many - you know - where do we begin? That's such a big question that we could do 10 hours of talking and, Lord knows, everybody does that. I mean, there's more analysis and trying to understand what feels like the craziest time in our lives, in history, who knows? Of course, there's been crazy times throughout history, but I do feel like that, as a musician and as an artist, all I can try to do is use the skills I have and the, and the, the fortunate circumstance where I get to play for people and make records, is try to use it to somehow provide some kind of distraction or peace or perspective that can take people out of all that for a few, for a few hours. Believe me, I have very strong opinions about a lot of things, and anybody who wants to corner me after a show will get an earful. But I really think that one – not the only, not the main – but one function of, of music and art is to rise above a situation, provide clarity, provide a new way of looking at things, where you come out of it, maybe with a little more awareness, a little more focus, and I hopefully I can do that with what I do. That's talking about world events and all that. But even in the music world, I'll put it this way. If I was starting out now, there are a lot of challenges for so many reasons. When I began in music in well before the 80s, when I started being a fan and playing music, it was easy – this is crazy to think now, but you could actually, and I worked in record stores, I was challenged with this – you could actually know every record that was released in a year. And you could say, here are the list of records that came out this year, and kind of know every one of them, because there weren't that many. And of course, now there's so many, and it's not a bad thing. More people are making music, more people are finding ways to do it and create. That's great, but it also means it's a lot more work as a fan, as a musician, as well as anybody to make sense of it all. And I'm kind of fortunate. I was grandfathered in at a time where enough people like what I do, where I keep doing it. 

Steve Wynn - Making Good On My Promises (Official Video)

What are your yet-unrealized artistic dreams, Steve? What’s something you've not yet gotten around to that you're eager to one day accomplish?

Just to make more records, make the best record I've ever made. And I know that sounds like a real generic kind of thing, but it's true. I'm going to be making two new records this July, two very different records, and I’m kind of excited about that, excited to go in, and that feeling that maybe when it's all done, I'll have made a record like two of my favorite records you mentioned this interview, “Crossing Dragon Bridge” and “The Universe Inside,” making a record like those two, where you're really, really, honestly happy with what you did and really satisfied and feel like you kind of broke new ground for what you could do and what you thought you could do. That's the most - that's a rush. That's such an exciting feeling. And I'm going for that every time out. So, really, going into the studio, or or walking on a stage, you hope you walk off saying, man, I did something tonight, today, this week, that I've never done before, and it was pretty exciting. That's it.

And lastly, Steve, we'll close with a question – when I was a DJ at WFMU, I'd ask everybody this question – if you had to recommend an album to like a 13-year-old or something, some kid about that zone where they're developing their own sense of the world and their own tastes, what record would you put in their hands to say, hey, you might get something out of this? 

Wow, that's a heavy one, because I could name a hundred easily. A lot of the records I loved growing up, besides just being great records, they taught me about music. You think about the Beatles records when they came out. When they came out, I was just a little kid, and I just heard them as Beatles songs – but eventually you’d realize, oh, that's a Motown song, that's an Everly Brothers-style song, you realize where they were coming from, and they taught you, they sent you down new paths of discovery. And I would recommend to a young kid a record that could do that. So, I could say so many. I could say “Exile On Main Street” by the [Rolling] Stones, but I'm gonna say, just because I’m on a Clash kick lately, I would say “London Calling,” because it really is just kind of a walk through somebody's great record collection as filtered through a band at the top of their game.

I think “Spanish Bombs” might be one of the best songs of all time. 

It’s fantastic. What a great song. Every song in that record, it's just a great record.

Stellar. Mr. Steve Wynn, thank you for your time today. You're appearing in North Adams, Massachusetts at the great Belltower Records on May 16. Thank you so much for your time today and your thoughtful answers and general enthusiasm. They are much appreciated.

My pleasure. And by the way, I think this will be my fourth time playing in North Adams, but the first time that it wasn't Solid Sound. I'm proud of this. I think I'm one of the few, and I could be incorrect on this, one of the few non-Wilco members that has played the festival three times. So I've kind of had a chance to play there with the Baseball Project, with The Dream Syndicate and with The Minus 5, but this time I'm going to be playing there not on the grounds of MASS MoCA. So, a new thing for me.

Breaking new ground in 2026.

Breaking new ground!

Steve Wynn
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Josh Landes has been WAMC's Berkshire Bureau Chief since February 2018 after working at stations including WBGO Newark and WFMU East Orange. A passionate advocate for Berkshire County, Landes was raised in Pittsfield and attended Hampshire College in Amherst, receiving his bachelor's in Ethnomusicology and Radio Production. You can reach him at jlandes@wamc.org with questions, tips, and/or feedback.
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