Trent Dabbs is a true, musical renaissance man. First and foremost, he’s a singer/songwriter with his own solo career, as well as a duo project — Sugar + the Hi-Lows — with Amy Stroup. But he’s also a visionary. Along with his wife Kristen, Dabbs founded the Ten Out of Tenn artists’ collective and Ready Set Records, which serves as a label and a development/production company. On top of that, he’s a much sought-after co-writer, crafting tunes with the likes of Kacey Musgraves, Ingrid Michaelson, Lori McKenna, and others — tunes that land him on television shows, radio stations, and Billboard charts with some frequency. He just has a way with a song.
Earlier this year, Dabbs released Believer, which put his indelibly melodic spin on a folk album. This week, he and the Ten Out of Tenn crew are celebrating the project’s 10th anniversary with an encore showing of their Any Day Now documentary at the Nashville Film Festival and a reunion performance at Ryman Auditorium. And, in June, Sugar + the Hi-Lows will drop their new album, High Roller, having just wrapped up a run opening for Musgraves. Not too bad for a kid from Jackson.
What were your initial dreams and hopes, coming up to Nashville from Mississippi?
When I worked with a producer in Mississippi, that was a goal in itself. I moved to Oxford because there was a producer there I had a musical crush on and wanted to work with him. When I did that, I moved here to find a band to play it and tour solo stuff. There was a handful of people that … if I were to say there were artists I wanted to emulate, it would be Josh Rouse or Ron Sexsmith — mainly writers, but when they play shows, they can pack out the Belcourt [Theatre] and make a consistent catalog and maintain their integrity, musically. Those are the heroes to me. Obviously, like Neil Young, there are icons, but I kind of loved the idea of any artist that could consistently play shows and have fans at like the Belcourt size.
So nothing too huge, but respectable …
Yeah, nothing too overwhelming. But they can still do what they do. When we moved here, I actually bought Josh Rouse’s Econoline, made some friends, and toured around the country with them and realized how hard it is to make a living. Our neighbor, when we moved here, I remember asking what he did for a living because he had two kids, and he said he was a songwriter. I was like, “No. What do you do for a living?” [Laughs] It never even occurred to me that writing songs for other people would be an option.
Did you shop your stuff to labels or was keeping it close to home always part of that original vision?
Well, the record that I did with Dennis Haring was on his imprint, so that was a little indie label. We talked to some, but never investigated it too much. Kristen has always been so good at a lot of the business side of it that it really just made sense to do things our own way. I’ve worked at a label. I’ve had internships at Elektra and stuff like that, just to see how the process works. And even talked to artists to see how difficult they are to deal with. [Laughs]
[Laughs] Ummm, yeah.
It’s just so much a matter of managing your own expectations, as an artist.
Absolutely. And that’s something that I admire about so many of the folks here — they, like you, aren’t aiming for stardom. They just want to do what they do and enjoy their lives, raise their families or whatever it is. It’s that middle-class creative thing.
The Lori McKenna thing is huge for me. Writing with her … she is an artist who can put out records that are so drenched in her sound and her life. And then people that would, in the world’s terms, be technically ahead of her can still cut those songs. That’s pretty ideal.
It really is. Has your artist’s career been everything you’d wanted it to be? And does it matter, at this point?
It definitely matters. It matters in the sense that I, obviously, want my music to reach a larger number of people than it probably ever will, but I guess if I can focus on what is there, rather than what isn’t, it’ll move forward. It’s like a lot of these situations with starting projects or producing or whatever … it’s chasing momentum.
Like with this new record, I completely made it under the radar and I kept adding sounds. Then I would peel them away because it didn’t feel like it was honest and I wanted to have something genuine. But I had so little expectation on the release because I’ve been so focused on Sugar + the Hi-Lows. So we just found a time to release it and, sure enough, as soon as it was released, it seems like it’s the most well-received album I’ve ever had. And I’m already kicking myself for not setting up a tour. [Laughs]

[Laughs] Yeah, it snuck up. I loved The Way We Look at Horses, but this one definitely feels like the folkiest thing you’ve ever done. Was that what the songs called for or was it in response to making a bigger piece with Horses?
I tell you what it was. Honestly, it was funny in a way, but there was one night here in town when there were two shows going on at once. My wife was at Bridgestone Arena watching Katy Perry and I was at the Ryman watching Dave Rawlings. And that show completely destroyed me. He had four over-hanging mics. And I’m such a fan of his anyway … but how authentic it was and how true to the folk artist that show was. Anybody who was there can tell you how blown away they were. I was like, “What is it about this?” It was not about the show. It was about the songs, not a spectacle or anything like that. There was no smoke and mirrors. It was just good sounds and good lyrics. It was so inspiring that it felt like a sort of exhortation or something to step up and peel back.
I remember, years and years ago, seeing Patty Larkin at McCabe’s in Santa Monica and sitting there thinking, “Man, if songs can stand up in that setting of just a voice and a guitar, then that’s a song right there.”
Yeah, totally.
Everything else is great and can make it even better, but that’s the nut. It’s also, being able to do your songs in a stripped-down way, that’s sort of job security. Because, even if you can’t afford to play or tour with a band, you can always go out and sing your songs.
I’ve said it a million times, but I can’t help it because the things I love, I have to talk about … but the Neil Young show for Heart of Gold with Jonathan Demme directing when Neil was at the Ryman singing about his dad and his dog — the most simple things — his delivery was everything. I was in the fetal position, losing my mind. My wife was like, “What is wrong with you?” I said, “I can’t talk about it!” [Laughs] But he was just channeling all this nostalgia. He’s evolved in so many ways, but has the same old Neil thing going on.
So what did film and TV licensing do for you, initially, when you started getting placements?
It was pretty much everything I could’ve wished for, initially. Now, there’s such a huge influx of people writing in that way, but at the time … whenever anybody asks what genre I play, I always say, “Heavy mellow.” I had a publishing deal here in Nashville for a year-and-a-half and I’ve always thought that “your work ethic directly affects your income, so I’m just going to work my ass off and write a lot.” There’s a token Nashville thing that happens where I didn’t really read the fine print. And I wrote maybe 120 songs and the company folded and I got to keep six. That being said, I’m glad I had the publishing deal because I had all these amazing musical blind dates, it refined the craft, and helped me meet people I would’ve never met.
So I just started to call the people that I actually enjoyed writing with or the artists I wrote with, when that company folded. Then I went to, “Okay. I need a job. I just lost this publishing deal.” Two months later, I get a phone call from L.A. and this company — that I actually had hit up a long time ago, but they’d said they already had Matthew [Perryman Jones] working with them — said they kept getting songs that I’d written with other artists across their desk and they liked “Your Side Now” and that song was going to be on Grey’s Anatomy. So, in that next two months, from two syncs, I made more than I did in a whole year of publishing. I was like, “This is unbelievable.” It felt like having a record deal in the ’90s.
Except you don’t have to recoup it!
Yeah. And it was also at a time where artists like Ryan Adams or Paul McCartney or whoever would be turning these things down. Now, they’re everywhere. It’s funny how that’s turned around.
Working with that company [Secret Road] led to collaborating with Ingrid Michaelson. This new record has done pretty well for her and there has to be some trickle down from that to you.
Yeah, I guess I can understand why people want to write Top 40 songs now. [Laughs]

[Laughs] Yeah. Or country hits.
Yeah. What is that, Life after God or something, where it’s like, “You become the things you make fun of.” With that, I’ve always been a fan of Ingrid’s. I think she’s ridiculously talented. Sugar + the Hi-Lows were able to open for her on two separate tours and, not at one point, did I hit her up and say, “Hey, we should co-write.” I wanted to, but ultimately, with an artist, it needs to be their idea. I would just watch her play every night and think of how great it would be to write. When she would just play piano by herself, it would be miles beyond some of the full band performances.
So, when it was her idea, I was fortunate enough to be on the other end of that. Her manager said that Ingrid was coming to town and she wanted to write, so we wrote two songs in what was one of her first co-writes ever. She came in and we wrote two songs in one day. I called my friend and we tracked them that night, and those are the vocals that are on her record and she’s never done that. We kept writing because it was kind of cathartic for her, I think, because of what was going on for her at the time in her life. We wrote the mellow songs and enough of those to be okay writing a pop song, to feel like we could try for that.
Obviously, Ingrid was already established when you guys teamed up, but you’ve always had a knack for working with amazing artists before they hit. Kacey Musgraves, Ashley Monroe, Joy Williams, Mikky Ekko … all of those artists, you were there first.
Is that your Spidey senses or is it something else bringing you into those situations?
Hmmm … I kind of think it’s just a love of music, being a fan of it, never stopping that side. Like, when Andrew Belle and I played a show in Washington, this girl opened for us, just strumming an acoustic in a coffeehouse vibe. But her tone was unbelievable and I was immediately going through the idea of, “Okay, this could be the first development.” And that became Youngsummer which is an artist on Ready Set.
And living here in town, you’re behind this huge red curtain that the world sees later. So when Ashley Monroe and Angaleena Presley are sitting in my living room singing, I’m like, “What is happening right now?!” Like, “This is real?” My kids are little babies and they’re sitting in front of these future icons. The first time we heard Mikky Ekko really bring it at a Ten Out of Tenn tour when we were rehearsing, I was like, “This is another planet.” [Laughs]
[Laughs] So you must feel like a proud papa or the coach who’s like, “Yep. Those are my kids!”
[Laughs] I get a lot of that. It’s impossible to escape the dad stereotype, especially on a bus with a bunch of artists. I would like to just sit in the front lounge and watch a highlights reel of all of our times. I’d be that guy.
Well, you must never know what’s going to be behind a particular door. You hear somebody sing and … I have my own stories like that. Sometimes you just say, “Hey, you’re pretty good. Can I help you?” And it goes on from there.
There was one tour with Ten Out of Tenn that was Ashley Monroe and Mikky Ekko and … it was such a random hodge-podge of people. I remember trying to talk Kristen into the idea of having a more eclectic thing because we wanted to see how far the brand had gone. But, on a lot of those shows, it was not sold out like many of the other tours. So it was crazy to watch one of the best shows I’ve ever seen and it not be in front of a sold-out crowd because they hadn’t started touring yet. So, it was little presumptuous to be like, “Well, let’s see what the brand has done.” But we had to.

Tell me about the founding of Ten Out of Tenn … when you guys first had that inkling of pulling something together.
The very first compilation had a few bands on it and some solo artists. The concept came out of a car drive that Kristen and I had coming back from Mississippi where we just putting all these CDs in the car of people that were from Nashville. I was like, “It makes no sense that no one knows these artists, really.” If I talked to someone in L.A., it was almost like they would smirk when you brought up Nashville. Now, those people are moving here, like tomorrow. [Laughs] But it was crazy that people had this assumption. I mean, it makes sense, since it’s country music, but …
So we just tossed around the idea of making a compilation and I’m obsessed with rating things out of 10 — it’s a silly quirk I’ve always done. After the very first tour, there were a couple of bands and a few solo artists and it morphed into the idea of multi-instrumentalist solo artists. And how to make it a show, where everyone is playing two songs at different times in the set. You’re cross-pollinating fans and we can sell merch collectively — we’d sell all 10 albums for $50. It was a show, so it wouldn’t be four hours of music with everybody playing 20 minutes. It’s kind of what Hotel Café was doing, but …
You took the show on the road.
Yeah, the live iPod shuffle on the road.
Are you the only person who’s been on board since the very beginning?
That’s a good question. Tyler James … I need to double-check that, but the ones that have been on it the most would be Tyler and k.s. Rhoads. Matthew, I think, has been on most of them. As far as putting the most time in, everyone that’s playing at the reunion show is the groundwork for TOT.
That’s going to be a great show … I’m going to assume.
Yes. It’s going to be the most magical evening.
Are you Skyping anybody in?
[Laughs] That would be so cool! We tried to bring in as many as we can, like Mikky Ekko. Getting everyone’s schedule, alone, is a full-time job.
Oh, yeah. That must be a nightmare. Okay, now Sugar … you had the duo project with Ashley and did an EP. Then, all of a sudden, you have your duo project with Amy [Stroup]. What is it about blonde singers and you?
[Laughs] Oh, I mean … I don’t know what blonde has to do with it …
[Laughs] It doesn’t. It has nothing to do with it.
Maybe growing up with ADHD has a lot to do with my projects? Amy and I were introduced through a friend at BMI and we have a lot of the same favorite artists. A lot of the Sugar + the Hi-Lows thing was a thought that I’d had when, every time I would talk to my dad, he’d have these blanket statements like, “Your music’s not good if you can’t dance to it.” I was like, “Huh? Does that mean you don’t like my music? Even slow dancing?”
We just grew up listening to Otis Redding and the Temptations and James Brown and all that stuff. I love that music. I heard the Chi-Lites “Oh Girl” in passing one day and I was like, “Okay. What is it about that song that just takes me to the place that I don’t feel like most music does anymore?” So I brought the idea to Amy: “What if we intentionally tried to throw it back but not be kitschy at all? Just go to the music that we love and grew up with. Write songs in that vein.” So we did. And we both knew exactly what players would make sense because they all love Motown. We started tracking those albums live like they used to. It was just this fun project that, basically, snow-balled in the best of ways. I think people can tell when you’re … you can’t fake fun, most of the time.
No. You can’t. And it’s so interesting because it’s completely different from Amy’s solo stuff and closer to, but still pretty different from, your solo stuff. It’s fascinating that the Venn diagram of the two of you is that. It’s cool.
It is cool. I’m definitely grateful for it. Something I’ve never been able to channel, solo-wise, is all of that stuff that’s in Sugar.
And you guys have a record coming out in June. This is a big year for you!
We do. Yeah. It is. We worked with Vance Powell to mix it and it was fun to watch him carve this sonic pumpkin and tell me Jack White stories. It’s so good. It definitely is this step forward — like 3.0 kind of sound. The leading single is called “High Roller” and, speaking of shameless, it is a dance move. Just straight up, “Let’s go for it and write a song about a dance move.” The video concept is in progress and the record’s coming out in June.
This article originally appeared on the Bluegrass Situation.