A Very Candid Conversation with Holly Montgomery

Holly (year unknown)

Holly Montgomery’s musical career has gone on for three decades. In the nineties she moved to Los Angeles and sang and played bass for various cover bands, as well as bands as Big Planet and the Mustangs (an all-female country band), and she also had a solo career.  By the early 2000s, she put her music career on hold for eight years when she adopted three teenage orphans from Kazakhstan

During the time when Holly was on a hiatus,  she left LA and moved to the East Coast. Around 2009, she  started her musical career again with her own band, Holly, and also her solo career. Several of the albums include I’m Only Human (2009), Uncanny Valley (2011), and Leaving Eden (2016). The latter album was in the first-round ballot and up for consideration for a Grammy Award. While Holly was in LA celebrating at Grammy parties, she contacted the Mustangs [Now known as the Mustangs of the West] and met up with guitarist, Sherry Barnett. From that meeting emerged the reformation of the Mustangs. The Mustangs got a record deal with Blue Élan Records in which they release an album called Time(2020). They also got a tour deal including a ticket on the South by Southwest Music festival, but COVID put a halt to their tour plans. 

During COVID, Kirk Pasich, the head of Blue Élan Records, was so impressed with Holly’s solo stuff and  encouraged her to work on her solo career. She recorded Sorry for Nothing (2022) during the COVID pandemic. Sorry for Nothing was produced by her guitarist Buddy Speir and Grammy-nominated producer Dave Darling. It was released on May 6, 2022. Holly plans to tour behind it, as well as continue playing with the Mustangs.

In this candid conversation, we go through Holly’s life, whether it was starting out in LA, becoming a mother, and her recent career with the Mustangs and her solo stuff. Special thanks to Nichole Peters from Jensen Communications for setting up the interview, but most of all, I want to thank Holly for providing me the opportunity to tell her story.

Jeff Cramer: So what got you interested in music? 

Holly Montgomery: Oh, gosh. Well, both my parents were musicians, and I had a ton of brothers and sisters in the house growing up. And to us, music was just cool, you know? We listened to a lot of music. I played keyboards in a band in my teens with my brother, Bucky. It was a prog metal band. My other siblings loved music too. We all dreamed about being in a band and doing all of that kind of stuff. I just never [chuckling] got over it, you know?

JC: Okay. Now, from what I've read, your career goes back about three decades ago.

HM: Oh. You know . . . career is a tough word as a musician, [chuckling]. Well, do you mean when I got paid for it, or when I actually started doing it in front of people? I guess that would be the band I was in with my brother, Bucky, when I was 14. I played trombone in the school band, and all my friends were into jazz. And then I played classical music in concert band in high school and college, and somewhere along the line I had my epiphany about playing bass. And I started playing bass, and that was it.

JC: Was this what you were doing in the ’90s? ’Cause I read that your career started three decades ago.

HM: No. In the ’90s, I moved to LA. At first, I went to Musicians Institute. I worked for Mike Tobias at Tobias Guitars, and I was just trying to figure out how to not be homeless and play music. And I started playing around, you know? I played with Suzanne Morrisette, a drummer who I'm actually playing with now, again, in a different band. We played in a lot of cover bands—we did five nights a week for a couple of years just to make some money playing music. Then Suzanne and I got in a band called Big Planet with Bill White Acre, and that was a great band. I mean, we made an album that the world never heard, and they really should have because it was a really great album. That was in ’92, I think. When Big Planet disbanded, I started doing a duo with Dan Bern, and so he was a huge influence on me as a songwriter. So I did that for a year or two, until it was like, "Eh, you know what? I'm a bass player. I'm a rocker chick, and I wanna play rock." So I spent basically the rest of the 90s and into the early 2000s trying to make that work.

 

Holly (year unknown)

JC: Now, I understand that you put your music career on hold to become a mom of three teenage orphans?

HM: I did, yeah.

JC: Could you discuss what happened there?

HM: When I started doing my band in the mid-nineties, it was just dealing with the music industry, and I heard, "You're too fat,” or, “You're too rock,” or “You're not rock enough" . . . whatever it was. It was just the constant barrage of negativity and people not doing what they say they're gonna do. A million people have written a million songs about having to deal with that [laughter]. And there was a certain point at which I wanted to have a real life. I didn’t want to be doing this so long that I woke up one day and say, " Wow, I never bothered to have a normal human existence." I never wanted to play music to replace real life—I kind of fell into it. I know that seems naïve to say, but I wanted to do something useful in the world, so I started volunteering for an organization called Kidsave International.

Kidsave might still be the only— I don't know—but at the time it was really the only nonprofit that was dedicated to finding older children to give them some sort of permanence in their life. You know, there's lots of adoption agencies for babies, and Kidsave wasn't an adoption agency; they're an advocacy organization. But really, nobody was advocating for older kids, and I just thought that was an incredible focus, so I started volunteering for them.

I hosted kids a couple of times and tried to help them find permanent families. And then one day, out of the pages of a binder that had a bunch of possible kids for a program, I saw a picture of my son, Ari, and I was like, "Oh, wow. Who is that kid? That's an intense look on his face." I got him into the program, and that's kind of the way I met him. I couldn't live without him, and then that changed the course of my life for the infinite better.

JC: So how long did you put your music career on hold?

HM: For about eight or nine years, I didn't do anything. I moved to the East Coast. Basically, it was kind of starting from scratch, which I still feel like I'm doing. I’m living there with the LA scars and  I was nine years older than when they told me I was too old for this. So, I just kind of started playing around town, and I came to find out that this area around DC has a pretty solid working musician culture.

I mean, it's not perfect, but I don't really know that many places like it other than a few oddball places, you know? You get paid for your gig. You don't always get paid enough, but it's not like LA or Nashville or New York, where people will get paid nothing. I got the meaning out of my life, and what's real in life. Now I'm doing it just for the love of music, so I don't care about the other stuff that much anymore.

So, I just started playing. The gigs I do range from the ridiculous to the sublime. I mean, one night I will be sitting in the back of a wine bar with nobody paying any attention to me at all, singing my songs. And the next day, I'll be in front of a thousand people at a venue. That's kind of fun sometimes.

At a certain point, I was like, "Oh, I wanna make a record!" And I made my Uncanny Valley record. I was just trying to put together a band to work around town, and I kept going through band members. So I finally settled on a great group of guys, and when I started playing with them, I got inspired to keep writing. That's kind of how I ended up where I am.

JC: I also understand you were in another band, the Mustangs of the West? Could you tell me a little bit about that?

HM: Sure. I was in the Mustangs in the '90s, kind of simultaneously with Big Planet and Dan Bern. So about that same time, I was doing shows with the Mustangs. The Mustangs were an all-female country band, and I didn't know anything about country music; I still kind of don't. I just have never listened to it at length. I'm not saying that I don't hear some country song and not like it, but it's not where my interests naturally go. But I really loved the songwriter in that band, Suzanna Spring, and they were fun to hang around with.

So we had a few years of doing some stuff and doing some touring. We got a publishing deal in Nashville. You know, people's lives change, and so the band disbanded. I mean, it was just one of those unbelievable things that you can't believe actually happened.

But in 2016, I put out an album called Leaving Eden. And I still never figured out quite how this happened or how it works, but it got onto the first-round ballot for a Grammy. And I was like, "What?" I didn't even know what it was. I mean, I've since learned what it means and what it doesn't mean, to be on the first-round ballot. I didn't know at the time because I wasn't a member of the Academy—and I’m still not—so I didn't nominate myself.

I was like, "You know what? There's very little chance that anybody's gonna listen to anything else from me, but I'm gonna go to LA and go to some Grammy parties, so what the heck." So I called up Sherry Barnett, the lead guitarist in the Mustangs, and also a very world-famous concert photographer. I said, "Hey, this thing happened—I'm on the first-round ballot. I'm gonna make myself feel a lot more important than I actually am, and I'm gonna go to LA, and I'm gonna hit a Grammy party or two."

And she was like, "[gasp] Suzie's gonna be in town! We should do a Mustangs reunion!" And I said, "What? But I'm only gonna be there a few days. I'm gonna be really busy." And of course, almost the whole trip ended up being Mustangs. But what we got out of that was a new-formed band. We added a fiddle player, Aubrey Richmond—which was always something that the band would've loved. Aubrey's just so great. And then, to my delight, we got Suzanne Morrissette to play drums—you know, Suzanne and I played in so many bands in the ’90s together. Suzanne and I play really great together, and so I was like, "Yes, okay."

And we did this video and this album. Sherry, the famous photographer/guitarist, had already been shooting photos for Blue Élan. So she took the video and the song that we made that day  and basically pestered Kirk Pasich [the head of Blue Élan Records] [chuckling] to take us. In fact, when Kirk signed the Mustangs, he said, "I don't care how much you weigh or how old you are, but I do want you to make good music." I was like, "All right. I can work with this guy. Let's do it." And so that's kind of what happened and the band got back together.

             The Mustangs (2020) (Holly is second from right)

But the Mustangs took a major blow because of COVID. We spent more than two years getting the Mustangs record done, and all the promo in place, and touring. We had a show at the South by Southwest festival booked, with Soul Asylum. We were getting ready to do all this stuff. Our tour was supposed to start on March 21, 2020, but the week before, South by Southwest got canceled, and everything got canceled. It's tough for the Mustangs because I live on the East Coast. LA is nowhere to live unless you have a lot of money. I'm able to do what I do because I can live below my means. The Mustangs just did an album in January of this year [2022], so we're hoping for a late ’22 release for that. [To hear the recent Mustangs’ single, “Crooked Road,” click here.]

JC: How did your new solo album, Sorry for Nothing come about?

HM: I started recording that album in 2017. I had gotten a couple of tracks into it, trying to figure out, "Okay, what is this album gonna be about?" and then all the stuff with the Mustangs happened. So me being able to stay concentrated on my album really kind of slowed down when I was trying to get the Mustangs record done and all of that. What I do as a writer and as a singer is very different than the Mustangs, but that's fine ’cause I'm the bass player of the Mustangs. So Kirk Pasich of Blue Élan told me, "You know, you should send down some of the stuff you're doing, and we'll see if we can at least license it."

I'm like, "Heck, yeah. That'd be great." So I sent it over to him, and he was like, "This is not for licensing. This is for an artist deal." And I was like, "What? What? Are you insane? Really?" Right before COVID happened, he told me "I wanna sign you to an artist deal. Let's do it." And then COVID happened, so it took forever to get the artist deal happening. But with COVID, we had the time now, and during COVID, we were able to do the record.

Now, the thing is, over the years of working with my own band that I'm in now, the guitarist in my band, Buddy Speir, is so fantastic. I had already self-produced the first two cuts for a record, but the truth is he's just so good, and he has such a unique stamp that he puts on everything he does. I was like, "You know what? You need to produce the rest of this record." And so finally I talked him into doing that, and he did a fantastic job.

We were able to do the rest of the record over the first year of COVID. And in that time, which I find to be amazing and awesome, and I'll never forget it, Kirk had passed on some of my music to Dave Darling. I don't know if you know who he is, but he's like— 

JC: I understand he produced six Grammy-nominated records.

HM: Yeah, he's a producer in how own right, and a great guitarist. He was in Boxing Ghandis in the ’90s, and he's producing a lot of really great people these days. He listened to this stuff and just became an über fan of what we were doing. He was like, "You gotta finish this record. Send me the stuff and let's do it." And so I would send the song, and he really helped us to focus on a direction for the album. Because as an indie person, who doesn't have to care about whatever her label thinks, if I wanna do one song that's like soft and pretty and then the next song is kick-you-in-the-teeth rock, it's my business. But Dave was like, "Well, if you want your next record to go further, let's keep it focused.” [laughter]. And of course, he was right about everything. So once we figured out the direction for the album, we said, “Okay, this is the formula that works. Some days after finishing, we were listening to what we did, we were just like, “Wow. This stuff is really good.”

                                              

Sorry for Nothing album cover(2022)

                      

JC: The first one I want to talk about is the single “All for Nothing.”  What was the idea behind that?

HM: I was going through a really, really rough patch. So, I actually really felt that way when I wrote the song. I mean, it was like I just could not find any light in that day at all. And at the same, my friend, Dan Chadburn, who is this incredible classical/new age piano player, and he does this incredible thing. He’s an improvisational composer, so you can tell him B-flat minor with a waltz feel, and he'll sit and concentrate for about 30 seconds, and then play ten minutes of music.I've always been so impressed by that. I was like, "You know what? I feel like such utter crap today that I'm gonna sit here, and I'm gonna be like Dan Chadburn, and I'm going to write the first thing that comes into my head, and I'm gonna take my time about it, and I'm not gonna beat myself up." And I wrote that song in one take. I didn't change one single word or anything. That's it. I finished it and was like, "Okay, well, I don't know that anybody's gonna wanna hear this song, but it sure does feel good to have written it.” It just so happened that in the writing of that song, for me personally, I felt like I completely and perfectly captured the feeling of that moment, which was, "I'm fighting off some despair right now." And then I wrote the song; I felt better.

The title "All for Nothing" is a euphemism for depression and despair. If you ever have struggled with any of that kind of thing, or even if it’s situationally depressed, which I certainly was at that time. I was just feeling like I put the vast majority of money and time and love and my life into things that not only haven't paid off, but are actively not good for me. And here I am, at my age, going, "Wow, okay. What has my life even been worth?" You know?

I mean, that's what you feel like in those moments. It's not something that I sit around and feel all the time, but I certainly feel it sometimes. I mean, I think every musician does because you can't live a life where what you do is perpetually undervalued. Even if you're not so great a musician, you're still undervalued [laughter]. And that's just the way that the world works in these days of instant downloading. So yeah, that's really what it was. Trying to scrape together that last bit of defiance that you feel before you just give in to giving up.

That's what the song was, actually. I haven't put it that way before, but that's what it was. It was like the person in the song, that's their one last little attempt to hang onto any shred of something. "Okay, I'm not gonna just utterly give in and disappear," you know? That's what it was about. [To hear a live version of “All for Nothing,” click here.]

JC: There's another song, "Looking for Lancelot." Excalibur is one of my favorite films, and so I certainly know the whole story of King Arthur, Lancelot, and Guinevere.

HM: Well, you know what? Okay, great. When the single got posted last month, a guy or two said to me, "Oh, I'd be your Lancelot." And I'm like, "Oh, dude. You don't know the story, then. You don't wanna be anybody's Lancelot. That's not the way that the story goes.”

JC: I certainly know how that story goes.

HM: With “Looking for Lancelot,” I had joined a songwriters’ group, and the guy who moderated the group made some comment about Daddy issues being "in" with female songwriters. At first, I was like, "Eh, dude, whatever." And then I'm thinking to myself, "Right, I've got Daddy issues. I'll write a dang song about Daddy issues. You want that? I got that."

I mean, my father died when I was seven, so there's always this thing hanging over my life of what would it have been like if he had stayed alive, and would I have felt more secure in the world, and would I have had better luck in relationships? There's a lot of things like that you just have to ask yourself. So it was a combination of that guy saying that, and a lot of women I know who have those kind of issues, like, “Dad yelled at me too much,” or, "Dad left us when he was young," or, "Dad was an alcoholic," or whatever it is that people individually have had to deal with in their life when they have a difficult relationship with their fathers. So I just kind of drew on my own experience and the experience of other people I knew who had those same kind of issues.

And I'm a huge history and literature nerd. I love all that stuff. I will travel thousands of miles. In October 2019, I went to England just because I wanted to put my index finger on Hadrian's Wall. And I did that. So, you know, I mean, I'll do anything. So I know all the various Arthur and Lancelot stories, from the medieval to the Saxon one. I mean, I know all of the differences. But, you know, the whole mythology around Arthur and Guinevere and Lancelot, and the downfall of the woman because she went with her passion instead of her duty. I think they're really great fodder for songs. [To hear a live version of “Looking for Lancelot,” click here.]

HM: One of your songs "For My Son”—was that one autobiographical? Was it about one of the three kids you adopted?

HM: Toward the end of my son Ari’s bachelor's degree, he was just kind of going through a hard time. He was just trying to figure out, "Wow, when I get out, how am I gonna pay my student loans?" All of that kind of stuff. Just regular hard-times stuff. And I just remember sitting and thinking. You know, you get so helpless when you wanna help, especially when you're a parent, and especially a single mother.

There's only so many things you can say that are gonna get listened to. Your kid knows that you love them more than anything, so when you tell them it's gonna be all right, they think that you're just saying that. You know what I mean? So there's all kinds of things like that—that as a parent, you feel impotent to be able to effect any sort of comfort, or change, or hope, or anything. And so it was just basically in that moment of going, "Okay, right now, I'd like to say some stuff to him.But he's not gonna be able to hear it right now, and so that would not be useful, so I just won't. I'll just write the song." So that's what I did. [To hear a live version of “For My Son,” click here.]

JC: It’s a bit jarring that the next song that follows “For My Son” is "Cunning Woman.”  "For My Son" sounds very uplifting but "Cunning Woman" sounds like it's telling a hard tale.

HM: Yeah. "Cunning Woman" came to me almost all at once, the whole idea for that song. So "Cunning Woman” is another archetype song. It's like the archetype of a woman/female/girl growing up and not fitting into the culture or family that you're raised in, and trying to figure out the world when you don't feel like you have a place in society where you are inextricably intertwined.

What do you do, as a woman, to go out into the world and find your power when you're not gonna be able to get it at home? This is something that I've thought a lot about in my life. And one obvious thing that women tend to do when they feel like that is the  use of their sexuality, which can take on many different looks. So this is just a song about somebody who figured out young that their body is their vehicle, and that they can do what the hell they want with it, and they can think what the hell that they want.

Do you know that term, ‘cunning woman’?

JC: No.

HM: So historically, cunning women were what they called the local witch. Those were the women who got blamed for being witches, or the ones who had special powers that everybody was afraid of because they spoke their mind and they didn't conform. So I mean, that's kind of what the song is about. About being an atypical female growing up in a place where you don't feel like you fit in at all.[To hear “Cunning Woman,” click here.]

JC: Any touring plans for Sorry for Nothing?

HM: Yeah, I'm working on the touring part of it now, trying to get a few things in place. I'm gonna go on and play as much as I can. I'm pushing as I have the energy to do, to solidify a couple of tour options that I have, just to be able to tour and see what people think. I mean, I have to give it to Kirk Pasich, you know, having the balls to find women who are, again, not your typical 23-year-old blonde, thin female. He's willing to do it.

So, yeah. I mean, I wanna tour. I wanna get out there; I wanna play it. And we have a lot of radio promo that's ramping up and getting into place. And I've got a bunch of radio interviews coming up while trying to figure out, "Okay, how can we make the music business work where the artist also gets paid along with everybody else?"

Holly on tour (2018)

JC: So what would you say that this whole journey you've taken—from playing in bands, becoming a mom, and now having two careers: your solo and the Mustangs—what would be your own reflection on all that's come? 

HM: I guess I would probably say that one of the blessings of bowing out of the music industry before I felt sullied by it was that I had an epiphany. Nobody is responsible for creating my adventures in my life. I can create my own adventures. I can record my own albums. Yes, they're probably not as polished as if there was more money behind it. But that doesn't mean that I can't live my own adventure.

So my words are that even though artists, musicians, photographers, visual artists, whatever, are grossly undervalued in terms of livelihoods, I still feel like the world needs it more than almost anything. I tell people all the time, "Even if you don't wanna play music professionally, just do it because the world is the better for it." Do it. It's the essence of everything that's human. We wanna make the world the best of what humanity is. It's like, in all the sci-fi movies, whenever we're trying to convince the aliens why they shouldn't wipe out humans, the warring human species, you know? Because there's this greatness in the art world of music and musicians that makes the world a better place. And so I hope that in my very small way I've contributed to that worldview. That's it.