Troubadour 77’s Anna Wilson and Monty Powell Unbox New Music and Cinematic Plans

Days after their first-ever trek to the Sundance Film Festival, Anna Wilson and Monty Powell — the powerhouse Nashville songwriting couple who perform as Troubadour 77 — are on a tear. Their first single in six years, “Boxes,” a slow-cooked, thought-provoking folk tune, dropped two weeks ago. And after relocating to Colorado as their home base, the couple is looking forward to a future filled with music festivals, filmmaking, and (yes!) retirement.

Honestly, the idea of slowing down is somewhat understandable, given all Monty and Anna have seen, heard, and experienced in their storied music careers. In the decades since they met and fell in love in 1993, while cultivating their skills as songwriters and producers at the height of the 1990s Nashville Music Row heyday, so much has changed.

“I moved to Nashville in 1993 right out of college … and after two years, got a publishing deal,” Anna tells me over a video call from the couple’s cozy Colorado digs. “And what that was back then was they paid you to write songs like from 9 to 5. It was your job. You went in Monday through Friday. You wrote songs every day, collaborated with other songwriters.”

That daily grind generated big hits for stars like Keith Urban and Reba McIntyre, followed by big commercial success before the Internet graduated from dial-up. Yet the challenges that have ensued in the digital media era — which made it harder to make a living as a performer, songwriter, and producer — have only strengthened their 25-year marriage. And their creativity.

We recently caught up with them to talk about those changes, in addition to the meaning behind their new single. The edited transcript is an excerpt of the full YouTube interview (below), between Troubadour 77 and Rockmommy editor and founder Marisa Torrieri Bloom.

Rockmommy: We are here with Anna Wilson and Monty Powell of Troubadour 77. So really, let’s get right into it. Where are you right now? Like physically in the world?

Anna Wilson: We are in Colorado. The ski hill is just right out the door, and it’s finally snowing, because the West hasn’t had much snow this winter, but it is snowing, and I’ve worn my snow sweater to try to inspire a snow dance.

Rockmommy: Oh, my God. We are so sick of snow here on the East Coast, as you know, Anna, being from Pennsylvania. I’ve known you guys forever, but Monty, tell us how you got to Nashville.

Monty Powell: I actually went to college in Nashville to be an attorney, and then discovered that there was such a thing as the music business. Like I didn’t even know that existed, like you could really do it as a career path, and not just have a talents count show up, you know, or all the things that we were told in the 60s.

So I was in Nashville already, and I was I got a gig selling, literally selling, not writing jingles for an advertising company. And it was during that time that I was like, I think I could, I think I could actually write these things. And so I was given an opportunity, and one of the first things that I was a part of was an Allstate commercial that played on the Super Bowl.

Rockmommy: Anna, were you in Pennsylvania. When did you get to Nashville?

Anna Wilson: I came to Nashville in 1993 right out of college, like 15 days after I graduated.

Rockmommy: That’s so cool. So country music was your first love? Or jazz?

Anna Wilson: I think I was a kind of simultaneous love. I mean, I would say probably my first love, and first introduction was kind of jazz music and the Great American Songbook, because my mom would play her piano in the living room all the time, and I would hear all these great old songs by Rodgers and Hammerstein and, you know, Irving Berlin. And so I really kind of started with that.

But then as I started getting a little older, like, you know, in great junior high and high school, my sister really got into country music, and so I started listening to that. And when it came time to kind of come of age and really try to do music for a living … country music at the time, in 1993 it was like a melting pot. Everybody was going there, and the 90s country thing was happening. And then, of course, I went to Nashville and I became a jazz artist.

Monty Powell: Make a note that my next band, the name is going to be ‘simultaneous love.’

Rockmommy: What was the scene was like in Nashville in the early 90s? Did you feel like the world was your oyster?

Monty Powell: Nashville was small town, you know, back in the 90s, not anything at all like what it is now. It also was geographically all in one place, you know. So there was a sense of community. Music Row where, literally, where all of the country music that was ever created came from, pretty much was no bigger than the size of college campus.

Everyone worked on these two streets, 16th and 17th Avenue, and every little house had been converted to a publishing company or recording studio. We had our local watering holes and local happy hours. So there was a real community sense there and people, because the industry was exploding, it was, it was okay to root for other people. There were plenty of opportunities for everyone. So there was a real sense that, you know, all ships would rise as the tide rose.

Then it’s completely changed now, 180 degrees. Now everyone is isolated in their own home studios. There is no common ‘Music Row’ sort of a thing. And the industry has been so compartmentalized, and the monetization of songs in particular, has dropped by 1,000%.

Rockmommy: Anna, how did you guys land those big artists like Reba McIntyre back then [as a professional songwriter]?

Anna Wilson: Well, a lot of it, I think, did have to do with what Monty just said. There was just much more opportunity and lanes for having your songs heard.

When I moved to Nashville in 1993 right after college, I kind of was there for a couple years, networking, meeting people, but I sort of, you know, quickly, after two years, got a publishing deal. And what that was back then was they paid you to write songs like from 9 to 5. It was your job. You went in Monday through Friday. You wrote songs every day, collaborated with other songwriters, and you had a person at your company called a song plugger, and they would take your songs once you wrote them and demoed them, and they would send them out to all the artists and the producers and the managers on those two streets that Monty was referencing.  

The sort of math that was involved of it happening every day, all day long, inside this very tight knit community, it really did raise your chances of getting your songs heard by enough people that, you know, you could get a Reba McEntire cut, or, yeah, Brooks and Dunn cut, or Billy Ray Cyrus.

The notion that the best song that’s out there on the streets [gets recorded] is gone.

Rockmommy: How did you guys meet, though? The timing could not be more perfect.

Monty Powell: We met at a concert in the rain the way everybody meets.

Anna Wilson: A Diamond Rio concert. He was their producer, and, at the time, I was their publicist. So we had reason to be backstage on behalf of the band, because they were playing the show at a big shed venue outside of Nashville, and we just kind of were working with the same band and randomly met backstage and started talking about all things music business and songs.

Rockmommy: What was your first date?

Anna Wilson: He said, ‘oh you want to write a song?’ You know, that was a pretty, like, you know, good pickup line back in 1993.

Monty Powell: That replaced the 1960s version of ‘you want to come upstairs and see my etchings?’

Rockmommy: What did you have wine or coffee or neither?

Monty Powell: We had … G chords?

Anna Wilson: Actually, as they say in country music, we have three chords and the truth!

Rockmommy: So you started Troubadour 77 after you’ve been writing together forever and raised two daughters. Is it 10 years that you’ve been doing this?

Anna Wilson: Yes, we started back in 2016.

Rockmommy: And you had a big festival and a huge lineup with some massive artists. Tell me about that.

Anna Wilson: Emmylou Harris, Ronnie Crow, David Pack from Ambrosia, Shawn Colvin, Billy Dean …

Monty Powell: Troubadour 77!

Rockmommy: Yeah, yeah, obviously. Troubadour 77!

Anna Wilson: Yes, it was a great festival. We started it in the mountains of Utah, where we used to live. We’ve now moved to Colorado, but it was at Snowbasin ski resort in Ogden, which is a town just outside of Salt Lake [City]. And it was really great. And then it got a little hampered because of the Covid pandemic, and that really kind of killed it.

Monty Powell: I mean, we were going on tour as Troubadour 77 spring of 2020 to support our record, and had to cancel six months of touring. And it just never, never came back.

Anna Wilson: So we pivoted, and we, we converted the band to an Americana duo. And we have a brand new single out that it’s our first single in six years! it’s called ‘Boxes.’

Monty Powell: The song is probably 15 years old, and we wrote it with another lovely songwriter. You know, in Nashville, it was just one of the random, ‘hey, let’s write a song not targeted at all for anyone in particular or certainly not foreseeing 10 years later us having an Americana duo’ and it matching the times and matching us, but it did. During Covid, we started doing what a lot of people were doing: Zoom concerts. We would play in our basement. We would broadcast it out, and everyone was doing meetings, and everyone was on was in boxes on their computer, just like we are now.

It just made us think of that, that song, which is about how we compartmentalize our lives to our own detriment, sometimes that’s interesting. We pulled that song back out, and we made the record on it, and we felt like it was really timely. We sat on it for a while because there’s no reason to release something now or not release it later. The world has completely changed. There is no schedule for make a record or release something. So we just felt the time was right now to kind of put this message out into the world.

Rockmommy: You say, compartmentalize. I want to drill down a little bit like, what was sort of the thought, like, you know, I’ve noticed people, not just metaphorically the boxes, like on the screens, but like, how do they compartmentalize aspects of their life in a way that they didn’t maybe used to do that.

Anna Wilson: You know, in some ways, I think people have always done that. I think that’s the human condition, you know, for survival at some level.

We wrote this song, really, I think it was actually 20 years ago …  we were exploring these concepts even back then. There’s a line in the song or the second verses, ‘we’ve got boxes for houses and boxes on wheels that take us to work in a box made of steel so that we can buy a box dinner for two watching the box that brings us the bad news’ …. [that] really resonated with the times now.

Rockmommy: So is Troubadour 77 releasing more in the near future?  What’s next?

Monty Powell: I think that there’ll be more recording from us. Again, we, we now do it at the rhythm that pleases us. We don’t dance to the tune of the industry anymore or any sort of a schedule. So there are some things in the can you know, that we could put out tomorrow.

We could, we could put out a song a day for the next month. And I don’t know we’re just, we’ll just see. You know, we have a lot of irons in the fire. We do a lot of things that aren’t Troubadour 77 that are still all music and songwriting based. And you know, also, I’m toying around with, what does retirement look like for someone that’s an artist and is in the business? You know, I think it’s a given that when you are us and you are one of us, that you don’t ever quit, right, necessarily, but you do completely change the circumstances and the leverage and the relationship to your art and to commerce, and so that’s, that’s, that’s a real place for both of us right now to kind of see, you know how that checks out over the next season.

Rockmommy: What’s your advice to other music industry professionals given the changing landscape? What would you say to someone who wants to sell a song to, say, The Bachelorette?

Monty Powell: I can speak to that because I’ve done this for a living, since I was, well, since 1979. . You’ll never be sane. So give that goal up. Look at what feels like an overwhelming uphill battle and just see the next step that’s in front of you, and in 2026 use the tools that have been given to you at your disposal. The low entry point level, there is no barrier to entry anymore to making great music. You can do it on GarageBand. You can do it in Pro Tools. You can sit in front of your iPhone camera and play a song on an acoustic guitar and get 5 million views.”