An Interview With Ricky Montgomery


If there’s one word to describe Ricky Montgomery, it’s “grateful”: for his fans, for their tour, for his career. That’s the theme that came up throughout the course of my conversation with the 28 year old singer songwriter. It’s over a year after the viral moment that launched Montgomery into stardom, and the artist is finally getting to bring their beloved music around the country in his first National Tour. Montgomery is known for their emotional and vulnerable songs and it’s no doubt that his shows are ones you’ll remember. I got to sit down and talk with Montgomery earlier this week and talk about things from tour, to song inspirations, to the secret to making it big in music today. 

We’ll be welcoming Ricky Montgomery to our city on Monday at the Songbyrd music house and you won’t want to miss it. Check out our interview below to learn more about the singer before you get to dance with him next week:

WRGW: We’re so excited to welcome you to DC – Songbyrd’s a great venue and I was just kind of curious what your favorite part of this tour has been so far? What do you enjoy the most?

Montgomery: Well, this is my first headlining tour. And I’m doing it with two of my best friends, Ben and Ryan from my other project the Honeysticks, they are in the band as well. And so I would say that the best thing so far has just been kind of doing it for the first time as our first headline. Like, like I said, so. It’s just the experience in general. I’m really thankful for that.

WRGW: Yeah, that’s so cool. And super exciting. Do you think that since your first national tour is coming off of the pandemic and a year of not touring and not doing live shows, is that affecting the experience at all? Like, how’s that affecting it?

Montgomery: Um, I mean, I think we’re all trying to be really careful. We’re being very strict with masks and stuff and all that. But me, Ben, and Ryan, also, we had a tour, with our other band in like, February 2020; we were supposed to hit the road in like, April or May 2020. And so we were all very, very excited. That was like our first national tour — we were direct support for that, not the headliner– but it’s really just a lot of gratitude. Because that was kind of like one of our big break moments. And then it got kind of sidelined by COVID. So I guess the way that it’s affecting the experience is just making us a lot more thankful to be here, and we can be cherishing the moments even more so because of that.

WRGW: I remember your song “Mr Loverman” and a lot of your music in general seemed to really blow up during the pandemic, especially on Tikok, so I’m kind of curious about that experience. Like, what was it like for you to see that song really blow up knowing you produced it a while back (in 2016)? Especially during COVID, with everyone relating it to it so much, like, how did that impact you? 

Montgomery: I mean, it was definitely a trip…It was different, I think, than most people’s big break moments, because I had it all in my house. And so I couldn’t really go and play shows and go do big things, and I was pretty limited in what could be done… But I do think part of the reason that “Loverman” and “Line Without a Hook” did so well at that time was because maybe it was just like a sad year. And, you know, at least “Mr. Loverman” is a pretty sad song. And so I think that was maybe the reason that it did so well…But it was mostly weird, because there were songs that I did when I was a lot younger, and I’ve kind of moved on from that sound, and hadn’t really been working with that type of writing in a while. And so to kind of have songs do so well, after I already kind of spiritually moved away from them was definitely kind of jarring, in a way. But I’m not at all not thankful for it. It was obviously like one of the biggest, most significant moments of my life and continues to be. But conflicting emotions, mostly because of the logistics. I couldn’t really fully take advantage of the moment. But all the good stuff has come from it. And as we come out of COVID I mean, it’s almost at the moment hasn’t stopped like, you know, you walk out there and do these shows and people are just as they were last year.

WRGW: Yeah –how has it been seeing the crowd react to those songs? I mean, after they’ve loved them for now over a year, has that been really meaningful for you to get to see that excitement and appreciation?

Montgomery: Totally. Absolutely…We’re also doing, not small venues, but we’re doing smaller than maybe we could right now. So we’re doing kind of an intimate tour. And it’s really cool. You know, we’re getting to kind of experience songs with, like a lot of energy in somewhat small rooms. So that’s been really fun, like every single person is singing along. 

And then last year we played the same venue before, in like 2019. And it was a great show then too, I think it was pretty sold out. But this one was just completely different; the meet and greet line was crazy. I’m actually like, having to kind of get better at things like Meet and Greet lines, because I realize like, oh, yeah, they’re really exhausting, actually.

WRGW: Yeah, I feel like I’ve been kind of overwhelmed going to shows and stuff since COVID has been over, so I imagine it’s just as if not more overwhelming. for the people performing! So kind of going off of that question about seeing your fans:  what would you say is your favorite thing about your fans? Who are your supporters?

Montgomery: I would say I guess they’re all really creative. And so it feels like I am making art for peers in a way. I feel like I’m seeing myself in the fans as like when I was a teenager, and I would go to shows and the way that I would feel about the artist that I was…My drummer was telling me a story. He said that he threw out his drumsticks to the crowd, last show. And the person that caught it, found them after the show and said that they were in a drumline and they were really excited to get that. So that was really cool to see. And then there’s a lot of stories like that. And people who are trying to get into social media videos, which is another thing I’ve done, and that I’ve stuck around for a long time. And yeah, there’s a lot of dedication, a lot of energy, like they’re really, really dedicated to the project. And so obviously, we appreciate that a lot. But I guess my favorite thing, if I had to have one favorite thing, would be that I feel like I’m making art for artists and not just for people who are kind of passively engaging with stuff.

WRGW: That story is so sick about drumlines, I actually used to do stuff like that growing up! And kind of more generally, what do you think has been the biggest inspiration for you in terms of going into music as a career? Like becoming an artist, stuff like that? What do you think has impacted you the most?

Montgomery: I always saw art as an outlet, and a way out of difficult situations at home…I didn’t have a ton of money and stuff, I didn’t really have a lot of money to go to college, so I feel like I always thought art is the only thing that I could really find fulfilling. And so wherever I found myself in my life, that remains to be true. It’s kind of like a justification for being alive, in a way. And yeah I just dont think I could do anything else.

WRGW: And then kind of stylistically, like, who are some of your biggest artists inspirations?

Montgomery: I’m a really big fan of Radiohead and the classics like, you know, Beatles and Joni Mitchell, and I like to like writers: people who kind of style themselves as songwriters. Right now one of  my biggest inspirations are people that kind of just stick to the craft like Dan Wilson, the guy that I’ve been working with; that’s kind of a mentor relationship right now, he’s a big songwriter in LA. And yeah, I guess people that I see as really strict about the craft. Mitski’s a big artist I’m into right now as well. Love Love Mitski. Yeah, those are a few but I could go on.

WRGW: Yes, I love Mitski! We’re so excited for her to come to DC this Spring too. Kind of bouncing off of that, like, if you had to name one person, who would be your dream person to collaborate with on a song — or the writing or performing of one?

Montgomery: I mean, honestly, I just said it, but Mitski’s a big one, a really, really big one. And Joy Again is an artist that I’m really into right now that I’ve been thinking about a lot with regard to this question. So those are my answers off the top of my head.

WRGW: Wow — I’m all in favor of those! Kind of more going back to the topic of concerts, and also your music in general: What are some of the big things that you want listeners and fans to kind of take away from your music or shows? How do you want the fans to leave the venue at the end of the night? 

Montgomery: I’ve never really thought about that, that’s an interesting question. I guess what I tried to do, especially with the most recent stuff, is try to just be as vulnerable as possible with the music. And so one thing that I really loved to do when I would go to shows as a teenager, and continue to go to shows as an adult now, I really try to kind of, in an almost tantric way, just let go of my judgments or feelings. I would love for the listeners to allow themselves to kind of get out of their heads for the duration of the show. To get lost in the moment, and kind of like, allow themselves that kind of brief, being, feeling. And yeah, just kind of just give themselves a break and allow themselves to kind of feel like the vulnerability that moment and then get back to their lives afterward. That’s yeah, just kind of that release, is I guess, the goal.

WRGW: Yeah. I feel like that is just the biggest thing for me at concerts… And a lot of your songs really touch into that vulnerability factor, and a lot of your videos do too —  I’ve loved watching your music videos so I’m kind of curious about that… How do you go about that (video process)? And like, what does that stuff mean to you?

Montgomery: Yeah, thank you. I mean, it’s, it’s kind of a different side of the same coin, you know. It’s just as important as the music to me. And so I try really hard to kind of give the song almost more clarity through the video. So sometimes I’ll have songs like “Talk to You” where the lyrics themselves don’t necessarily give you the full meaning. And so I try with video to kind of almost paint the rest of it, via whoever is directing. Or, you know, the last video, “Started for Me”, that was an animated video. So I’ll meet with the person who’s directing or making the thing and everything is about my vision for it. Occasionally, I’ll actually kind of build it myself and write the video and then they can kind of make it better than I could on my own. And then with some older stuff, I’ve actually done a lot of the work myself and so yeah, I guess I tried to take the song and then finish the meaning with video. That’s the simplest way that I can put it.

“Talk to You” Music Video

WRGW: That’s really interesting. I’ve always been kind of more curious about that from an artist’s perspective, so thank you. And then just kind of also going off of that I know a lot of your virality and your success has come from Tiktok and the internet. So I’m kind of wondering about your thoughts on how the Internet has impacted the music industry?  Has that changed how you go about anything? 

Montgomery: Well, in my case, I’ve always done it that way. So in high school, I played local shows and stuff. And so I was 14, and I felt like in the scene that I grew up in, in St. Louis…there’s not a very big music scene in St. Louis, for example. And that’s probably the case for most people, where the town they live in is not necessarily like a mecca of music industry life. And so, for me, I remember the day that I downloaded Vine, it was the day after the app came out. And I remember thinking to myself, ‘Okay, this is my trampoline for a music career. If it’s ever going to happen, it will happen here.’ So I was always really, really intentional about that. And Tiktok, I almost was too jaded for. I totally knew about it. I knew about But I’ve gone so deep into Vine…knew the people that made the app.. I was as deep as you could be in the app. And so I just didn’t have more energy available for video platforms. But then, of course, like the hand of God came down through “Mr. Loverman” blowing up and said ‘You have to keep doing this’. And so now, as much as I can, I still use the app  but like, it’s not the same as when I was new to it and there was a kind of novelty to it. Now, it’s much more kind of by the numbers, but I still do love it.

I think now, I mean, the truth is that there’s no music industry without the Internet. And that’s been the case for decades. So any artist that thinks that they can get through, you know, the early stages of their career without taking advantage of social media is, you know, unfortunately, maybe not going to succeed anymore. And that’s just because of the way that it works. And I tell that to everybody that asked me that question. So yeah, if you are trying to blow up get on Tiktok, and then whenever Tiktok fizzles out, which eventually it will, go on to the next thing, right when it happens. 

WRGW: And then my second to last question goes right off of that. I’m curious. You said to get on Tiktok for stuff like that (big break moments) But do you have any other advice for anyone who are looking to kind of break through and have that kind of viral moment?

Montgomery: I mean, if the advice is getting a viral moment or growing in the context of the music industry, really, the answers are all Tiktok right now… I can tell you as a person signed by a label, like, all the labels are hyper fixated on Tiktok. And it’s essentially like its own arm of the music industry. It’s like, there’s radio, there’s streaming, there’s tour,  and then there’s Tiktok; And they’re all as big as each other, more or less, you know, you could probably find some variants. And it’s probably some other things that some people do…but every single artist in the world who is on a music label, indie or major, is being told to make more Tiktoks. That’s a fact. And so I would say, take that knowledge, and then use it and understand that that’s where the eyes are. And that is the best use of your time. Also you need to get better at music, you know, and take lessons and practice and play shows and get your chops up. But also, Tiktok is , in the present moment, as important as all those other things, if not a little bit more important, with respect to the question of getting a larger audience.

WRGW: Yeah, so there we go. I used to work for a music festival this summer, and there was such a big focus on Tiktok. So like, that is true. Everyone should be using Tiktok more. Then my last question:  you’re doing this tour now, is there anything we can expect after the tour like, anything for us to look forward to? What’s up next for you and for the band?

Montgomery: Yeah. Really, once I get home, I’m getting right back to work. I’m going to be putting out a small EP (next year), and then hopefully next year, as well, I’ll have LP out. I’ll be working around the clock. There’s gonna be more tours next year. More places, we will see where the ships land, because there’s going to be some tours pushed behind the scenes that have gotten delayed after the Delta variant happened. And so yeah, I will direct the audience to just watch my social media accounts for updates on that because I don’t want to say anything now and then it gets contradicted later… So yeah, that’s kind of it. I mean, more music, more shows, more stuff. In a nutshell. That’s the future.

WRGW: Wow. I’m excited. I can’t wait for that.

Montgomery: Yeah I’m excited for Songbyrd too, that’s the only show that a guitar player who’s with us hasn’t played at, so that’ll be a new experience, specifically, for all of us, so yeah we’re really excited.

WRGW: Well that will be so fun, and we can’t wait to have you.

Montgomery will be performing at Songbyrd Music house this Monday. You won’t want to miss this show.

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