This is part of our ongoing series on musicians who perform in The Berkshires.
Since October 2021, Milton has performed in The Berkshires nearly twenty times at several different venues. He has more shows coming up this summer, including this Friday, June 23, at the Egremont Barn. I got to catch up with Milton over Zoom to learn more about him and his musical journey. One thing that impressed me as I researched Milton’s twenty-year career is how much of a music scholar he is and how diverse his tastes are. I hope you’ll see that in our conversation, which has been lightly edited for clarity.
You’ve performed extensively in The Berkshires and have more shows coming up this summer. What keeps you coming back to The Berkshires?
I go back a ways with performing in The Berkshires, starting out at the Dream Away Lodge twenty years ago. I’ve played at other venues like the Green River Festival, Guthrie Center, the old Club Helsinki down in Great Barrington, and the Gypsy Joint when that was there. So you can see, I’m a Berkshires-loving guy.
What is it that makes the Berkshires special?
It’s a huge number of things. I started going to the Berkshires as a small child. My great-uncle had a little house outside Great Barrington near Egremont that we used to go to. And from New York, it seemed like a faraway country, like a mythical land. By the time I was about ten years, my best friend’s parents bought a house on Indian Lake in Becket, and I started to go up there with him on weekends. I remember that we would sneak off, underage, to a place that no longer exists called the Bonney Rigg Inn, where there would be Honky Tonk bands. And we learned about the Dream Away. So growing up, it was just a place that I loved.
I’d been living in New York City since I was 19 after growing up in the suburbs of New York. And when you’re living in the city and playing gigs, gigs are what brings you to nice places. Otherwise, you can’t afford to go on vacations. It’s always been a great part of every summer for me to get to go play in The Berkshires – whether we go for the day or spend the night. Years of history, friendships, and music created a love of the area. It’s really one of my favorite places.
You’ve released five albums; the most recent was Studio City in late 2019, just before the pandemic. Can you tell us a little bit about that album and how your music has evolved since the first album, which was released in 2003?
Studio City, I think, is my finest studio effort and the most studio-heavy record I’ve done. As a guy who came at it first as a songwriter, my records picked up studio craft as they went. I used to be very intimidated by the studio, and as much as possible, tried to capture the “live thing” in the studio. And this was the first time that we really were able to get loose with all different kinds of messing around – whether it was having a full orchestra on one of the tracks or using old samples.
We used a machine called an Optigan, which was similar to the Mellotron, an early synthesizer, where every key was connected to a tape machine. The Optigan was the vinyl equivalent where when you press buttons, you would play a recording by an orchestra of the note that you wanted to play. All this stuff has been digitally archived and you can use these instruments virtually now. So that stuff made it onto the record – crazy things I’ve never been able to do before.
We had a whole tour booked and played the first couple of dates. We had the record release at City Winery. Then we were going to do a follow-up show to begin the tour – I remember the date was the 13th or the 15th of March [the week the Pandemic hit], and we had to play the show out of my room in Brooklyn.
My first couple of records were a little bit more folk-Americana, and I’ve been throwing in all the other stuff that I like over the years and getting more comfortable with that. I suppose I felt a little pressure in the beginning to find a niche or something, industry-wise, which I find all beside the point in terms of music and art.
In the end, I just want to make something good and hopefully interesting and nice to listen to. So with each album, I put away another layer of worry or discomfort with going in any direction I want it to – so it goes in a number of directions. I think the live shows do now, too. I like so much music, why does it have to be one thing or another?
Do you have another album in the works?
Yeah, it’s in the works. In fact, I have some studio time here in Brooklyn in just a few weeks with some really great guys. But it’s slowly moving along because, as a new parent, it’s hard to find the time. I get a few hours of writing time a couple of times a week. I have a little studio where I go. And the songs have been finally starting to pile up. And so I think within a year, I’ll have an album’s worth of stuff.
“In the City,” which was released in 2003, is one of your most popular songs. When we saw you at Dream Away Lodge recently, many people in the crowd knew the words and were singing along. Can you tell us why you think that song has resonated so much with listeners?
That has been my most popular song – it came out on my first solo Milton album and was largely popular in the New York area, although not at the time that it came out. The second album has a live version of it from The Living Room in New York City, which is a club where I played regularly for years and years. That version got picked up by several college stations around the country and some outside the country as well.
For me, that really was a quantum leap in my professional life. I had worked various day jobs, finished college, and played in bands around New York City – old clubs that don’t exist anymore, like Brownies and CBGBs. And then, I decided that I really wanted to just focus on being a singer-songwriter. I was working in the daytime as a Spanish teacher, and there was a history teacher that I worked with that said, “with what you do, you should be on FUV [WFUV],” and I said, “What’s FUV?” WFUV is the Fordham radio station, and they called their programming format “city folk and more.” It was like folk but urban folk.
When I made my first album, the label out of Raleigh, North Carolina, that signed me sat me down and said, “Look, this is a labor of love to a mom-and-pop label run by artists. We have no budget to promote you in any way. We have a bunch of old cars, so you can have one, and then you can drive anywhere you want in the country – in a way that’s your promotional budget – it’s this car.”
So I got this great old car, and that was cool. I had no money and I had no publicist, and at the time, I played coffee houses. So I literally got a bubble envelope with a CD and a little personal note and sent them to every DJ at WFUV and several other stations. And then I made a nuisance of myself and called and emailed everyone. There is a DJ named Vin Scelsa, who in New York is kind of famous, and had been on WNEW for many years. He had a Saturday night program at FUV. He wrote me an email, and he said, “Listen, if I like it, I’ll play it, but just leave me alone. Stop bothering me.” And so I said, “I will, I promise, but do me a favor and just listen to it.” And a couple of hours later, I got an email from Vince that said, “Hey, this is pretty good.” He was kind of surprised. And he really took a liking to it. And he played four or five different songs on one episode during pledge week and talked about it. It turned out that the Station Director heard him playing it, and really liked it, and put it into heavy rotation.
It was something very much about the format of the station, and it being about New York City, and lyrical singer-songwriter stuff, that really struck a chord with them – and a lot of people in the New York City area. But I’ve had people come up to me and say, “I love this song because it helps me connect to my childhood in Baltimore.” People just love that urban experience. And for people like me, who grew up in the suburbs, where the city was the land of dreams, they share that experience. It’s been wonderful to connect with people – I’ve received emails from soldiers abroad, people who train for the marathon, who have said all kinds of wonderful flattering things. So it’s been cool in that regard. That never translated into being a wildly famous person but it did get me started. As a professional, I’m able to get a lot more bookings, and meet a lot more people and artists. So I am grateful for that.
Is there another song of yours that you are particularly proud of or really enjoy performing?
There are favorites of the month or the year, then also the ones that endure in their appeal to me. It’s a very simple one on the second album, self-titled, that’s called “Sister of the Virgin Sky.” It’s trying to do something along the lines of Taj Mahal and stuff that I liked when I was a kid. It’s real simple. It has a blues structure but in a major key rather than a dominant key, which is what is normally associated with blues. And it’s kind of positive yet pokey, bluesy, and very personal. I really like the song – it still gets me when I do it, so it’s one of my favorites.
I like the simplest ones the most. I tell people who know my stuff might, and perhaps associate me with lyrics, and being a bit heady, that if I could have written “Sugar Sugar” by The Archies, I would have been delighted. A simple little ditty that sounds nice and is meaningful – that’s all I’ve ever been trying to do. One of my favorite songs in the whole world to cover and play it over and over again is “Crazy Mama” by J. J. Cale. It is close to nothing in terms of chord changes; the lyrics are just one and a half verses – it really is very, very simple. And it’s gorgeous. If I could do that all the time, I would.
Can you tell us how you got started in music?
My earliest memories of trying to write songs is at about three or four years old. I just had an idea that I wanted to sing something very dramatic and wonderful and was trying to do that. My obsession with music probably started with hearing The Beatles on my mom’s old copy of “A Hard Day’s Night” when I was about four or five. I learned how to operate one of those old briefcase record players that we had at the time. And that was it. I was done.
I hear the crackle of the record, I hear the first chord [🎶 Milton vocalizes the opening chord🎶] of “A Hard Day’s Night” and just think about the excitement of that record. And keep in mind, I was born after Beatle mania. But the excitement of the music, the beauty of the harmonies, the joy in it, it just sounded like heaven to me from the get-go. Then when I saw pictures of them – and I’m the youngest of a bunch of brothers – they looked like a bunch of guys who are best friends with each other, singing like angels, and being chased down the street by girls – I thought, “well, what in the world is gonna be better than that?” And my feelings about that haven’t really changed as far as the joy of making music.
But then from that point, to actually doing it, was a while. As a kid, I hadn’t connected the idea that I could actually do it. It just seemed like it was magical stuff that magical people did. Even though I was already writing songs every night after lights out in my bed, and my notebooks were filled with little ideas for songs – little rhymes that I would imagine were songs. I didn’t really play until high school, when I formed a band. Even then, I would joke about it or say it was not serious. It wasn’t until my senior year of college at NYU that I began to jokingly say that I was coming out as a musician. I finally admitted it to myself.
It was like, okay, it seems crazy, it seems like everybody dreams about doing this, but very few get to do it. No one’s ever told you that you’re talented at this thing. But I just really desperately want to do it. I don’t like the idea of living this life and not trying this thing and just daydreaming about it. So I’m going to go ahead and try to do it. At that point, I started to play the open mics at college. I started to play every little gig that I could and tried to write songs which, to my ears, started out kind of corny and lousy and just got a little better, inch by inch. And I just kept at it.
I remember my first gig in New York was with my older brother, who was playing at St. Mark’s Place, this little cafe, and he let me go and open up, and I thought I was gonna die – my hands were shaking and everything. But I did it, and then it got a little easier, bit by bit.
In my high school band, I was a drummer because I didn’t know how to play anything else. I never took any lessons and still haven’t – I learned everything on the job over the years. I wrote all the words because I couldn’t write music yet. But I was always unsatisfied with what we were doing, and I would tinker and say, “What if it went like this?” And so eventually, I picked up a guitar because I wanted to write the songs.
Normally, this is the point in the interview where I ask you about your musical influences, but you addressed that question thoroughly in a blog post you wrote back in 2016 that, by my count, lists over 100 influencers, including Bob Dylan, Paul Simon, Randy Newman, Joni Mitchell, and your mentor Chris Smither. Since you wrote that blog, have you reflected on that question any further – is there anyone new that you would add to that list?
I don’t know if there’s anyone new that I would add, I’m kind of stuck on old stuff, and I’m not that good at the contemporary. At different times in my life, I’ve really freaked out on one thing or another. I remember when I was making my first album, I was completely lost on Lucinda Williams’ Car Wheels On A Gravel Road. I thought it was a perfect album. I listened to it all the time. I wanted to make one like that. And in its own weird way, if you listen to my first album, you can almost hear that I’m going for that. I haven’t sat down to listen to that album in twenty-odd years, so it depends on what I’m going through.
I was listening to The Kinks like crazy. I think Ray Davies is very underrated, even though he is incredibly legendary and successful, since people don’t realize the depth of those compositions.
You also mentioned Nick Lowe in one of your blog posts as being very influential.
I have a lifetime love affair with his stuff. I remember my brothers were punk rockers and they were really into the Ramones. The Ramones made a movie called Rock and Roll High School. There was a scene where the teenagers are at a Ramones concert waiting for them to come on. And there’s a Nick Lowe song playing in the background, and I said, “What’s that?” My brothers are thinking, “What’s wrong with this kid – the movie about the Ramones. Why don’t you learn about the Ramones?”
I literally tracked it down – the song called “So it Goes,” and it just opened up a life of “Lowe-love.” I can’t tell you how many times I’ve seen him in concert over the years and have all of his albums, nerded out on his whole career, and read his biography. I just love the way he puts together a song. And in his own way, although it’s primarily within a rock and sort of country idiom, he’s like Irving Berlin in his own kind of way. He’s a comic-poet kind of writer.
What I love about that is when the craft is so good that it’s seamless. You have somebody who’s very literary in their own way. They’re really thinking a lot about how the thing is put together and yet it comes off conversationally. You just get to enjoy it. You don’t sit there and say, “What is this strange, obscure metaphor? Isn’t that amazing? Aren’t I listening to a deep person?” No, you just enjoy it.
It’s like when Irving Berlin writes, “the night was splendid,” and then he rhymes it with “the moon descended.” This is a man that never finished high school, but he’s got the craft, and he has a mind for that kind of thing. And it just makes these little delightful pieces of light verse that we get to enjoy and repeat and think about and contemplate and emote with. That’s the greatest, as far as I’m concerned.
Are there any artists that you’re listening to now that you’d want to share?
This morning, I got up, I got onto the elliptical machine, and I listened to The River by Bruce Springsteen because I realized there were parts of his catalog that I never really listened to. Obviously, I know “Hungry Heart,” and there’s a song called “Two Hearts” that we had to play for a wedding once, so there were a few songs on the album that I knew, but for the most part, I never had a freakout on that album. Born in the U.S.A. and Greetings from Asbury Park, N.J. I played like crazy, but this one [The River], I never did. So I put it on this morning.
And just now with the baby, I was listening to Bob Marley and the Wailers’ early music, which is the ska days of that group, and the other day, I put on Clare Maloney’s new record [Daybreaker] because I read your interview. I had met her at a place where we both played in Westchester – she was really nice and really cool. But I’d never listened to her music. So I figured I’d give it a spin.
I see that you perform in three configurations: Milton, the Milton Trio, and The Loyales.
Yes. “Milton” can be anything from just me showing up by myself to a 10-person band.
Milton Trio is something I do between the ticketed shows and the singer-songwriter venues. I just am always playing because I make my living that way. We will play at a restaurant – three hours of music, and we may play anything from Irving Berlin to Bruce Springsteen to Jimmy Cliff to my stuff over the course of the night. I won’t be as focused on my own stuff. I probably won’t interact with the audience as much, probably not as much banter, because it’s not a listening room – in those places, we’re just playing good music for your enjoyment. It’s not like a singer-songwriter show where the audience has that expectation of interaction and stories.
The Loyales was primarily formed to play weddings, private parties, and company functions. The story behind that is that when you’re a musician, a lot of people will come up to you and say, “Hey, can you play our thing? We’re thinking it would be great if we had you at our party.” And many years ago, when someone would ask that, I’d say, “Sure,” but it’s a private party, so we’re gonna have to learn stuff. And I tried to imagine the biggest figure in the world. “So that’s going to cost you $1,000,” which would seem like an incredible amount of money to me at the time. That’s how really broke musicians are. And people always say, “Oh, sure,” because it was a bargain. I didn’t know that at the time. And we would do this all the time and then realized at some point, this would be a good thing to do organized, but I didn’t have any idea how to do that.
We were playing a wedding somewhere in South Salem, New York. A guy came out of the crowd to say hello and said that he ran an agency. He said, “I think you’re better than all the bands in our agency, and if you’re in interested in representation, let’s talk.” We became very close friends and started to work for his company. He really helped me to get that band up and running, and it’s been a way to stay afloat and make a living. And we do so, not by playing the top 40 hits of the summer, but by playing the whole catalog of stuff that’s meaningful to me and to all the musicians that I’m friendly with and play with from the New York scene.
And it’s great. It’s a joy, to tell you the truth, because, as a singer-songwriter, you love all this stuff. You don’t get to do the old stuff. But on these occasions, I do, and I’ve just been fortunate – super lucky. I get to curate what we do for the most part. The Loyales have literally about 300 songs in their repertoire. It’s all just stuff that we like, running the gamut from country to bluegrass, blues, R&B, New Orleans, Motown, Stax, Chicago soul, and classic rock, and all of the stuff that we grew up loving, whether it’s the Stones or the Talking Heads, Nick Lowe, Elvis Costello, or T. Rex. I get to play all that stuff, and that, to me, is just sheer joy of its own kind.
This coming Friday, you’ll be performing at the Egremont Barn, where you’ve played in the past. Will you be alone or playing with a band?
I’ll have the band. A great band, in fact. The Trio will make up most of the rhythm section, but also, we will have a great piano player named Pat Firth, who’s a close friend of mine, and most often, you would catch him out on the road with Carsie Blanton. We don’t get to play as often anymore because Carsie tours a lot. So Pat’s going to come with us to the Barn. For shows like the Barn – listening room venues, ticketed venues – I want to really focus on the presentation and give the audience a little something different every time. I really love it when I get the chance to play with these players that I love so much.
Do you have anything special planned for this particular show?
Yes, we will play new songs, unreleased songs. A couple that I think haven’t even been played live yet. Maybe even a cover that we’ve never done for live audiences. And then I always try to do some of the older stuff but in a slightly different arrangement. There are a lot of songs from the albums from the early 2000s that we still do, but the arrangement is so different that people might not even recognize it, even if they heard the record. And that just keeps it fun. And also, because you’re never really done. You release it, okay, but you still tweak it and find something new in it. So we mess with arrangements a bit, too.
Is there anything else that I didn’t ask that you’d like to share with our readers?
I think The Berkshires is an incredibly special place to dig and behold music, and I’ll be around a lot this summer. My connection to Berkshire audiences has been many years in the making, and I absolutely love it. Several years ago, there were only one or two places you could see live music in the Berkshires beyond Tanglewood. Now, there are a lot of really good venues that have popped up, and so I encourage everybody to go check out all this stuff happening in all these places.
Yes, I like to say, “Get off the couch and go out and support live music in The Berkshires.” I’m really looking forward to seeing you next Friday Night at Egremont Barn.
You can learn more about Milton at miltonmusic.com. You can find his music on all major streaming platforms, including Spotify, Apple Music, and Amazon. You can also follow him on Instagram and Facebook.
— Mark @ Music in the Berkshires