You might call Oklahoma singer-songwriter Ken Pomeroy a reluctant artist. “I wouldn't say that I wanted to be a singer-songwriter,” she says. “I've thought about quitting playing live so many times, but every single time, I would still be writing songs for myself.”

Pomeroy just can’t help songwriting. “The easiest way I can explain it is like when you have to go to the bathroom,” she says. “You just like, ‘OK, I know that I need to, so I'm gonna go do that.’ And it normally it takes like an hour and a half, and then I have a song.”

Music found Pomeroy at an early age. She liked singing and writing poetry, and when she heard John Denver’s cover of “Leaving on a Jet Plane,” she was compelled to write her own songs. “I think it just was one of the first times that music had made me feel something,” Pomeroy recalls. “I thought it was really cool that a song or a person singing a song could make me feel like that. And I wanted to do that, or at least try to do that.”

Pomeroy’s latest album is 2025’s Cruel Joke, released on Rounder Records. Coming up on August 20, Pomeroy will release Tonight’s News, an EP of six cover songs, including Gillian Welch’s “Look at Miss Ohio,” that she recorded in a day at Wilco’s studio in Chicago.

In the midst of a very busy summer of touring, Pomeroy and her band were in the Twin Cities to play a show at the 7th Street Entry in Minneapolis when they took time to stop at The Current studio to record this session with Radio Heartland’s Mike Pengra. Watch and listen to the full session above, and find a transcript of Ken Pomeroy’s interview with Mike Pengra below.

Interview Transcript

Mike Pengra: Really happy to be in the studio with Ken Pomeroy today. Ken, thank you for coming back to Minnesota.

Ken Pomeroy: Absolutely, we love it here.

Mike Pengra: Yeah. Ken's latest album is called Cruel Joke. It came out last year, actually, and it's been one of my favorite albums since I got it.

Ken Pomeroy: Thank you.

Mike Pengra: You're from Oklahoma. You grew up wanting to be a singer-songwriter. What got you into that interest?

Ken Pomeroy: I wouldn't say that I wanted to be a singer-songwriter. I think that the path laid itself out a little bit. I showed interest pretty young. I was writing poetry and being weird whenever I was little, and then I heard John Denver for the first time. That's a big, big part of my, you know, coming-of-age story.

Mike Pengra: "Leaving on a Jet Plane," right?

Ken Pomeroy: "Leaving on a Jet Plane," yeah, that was kind of the whole, the whole reason I got into playing music, and I kind of was always surrounded by music. My dad was in a band. You know, there were family members and friends who would play music around me, and then I started playing guitar, and it just kind of like snowballed into this bigger thing that I'm thankful for.

Mike Pengra: Yeah. You started in — you're in your early 20s, now — so when you started, what was it about "Leaving on a Jet Plane" that got you interested?

Ken Pomeroy: I think it just was one of the first times that music had made me feel something. Like, I heard that song and I just remember feeling like sad, and I thought it was really cool that a song or a person singing a song could make me feel like that. And I wanted to do that, or at least try to do that.

Mike Pengra: You've been writing songs for a while now, and tell me about your songwriting process. I mean, and what does it do for you?

Ken Pomeroy: Ooh, OK. The process is kind of quick; like, it kind of is a spark of something. The easiest way I can explain it is like when you have to go to the bathroom. You just like, "OK, I know that I need to, so I'm gonna go do that." And it normally it takes like an hour and a half, and then I have a song. And it's like ... I don't know. It's a weird thing, but it is definitely a ... It's definitely something that I need in my life to be able to process things.

Mike Pengra: If you didn't have it, what would you do?

Ken Pomeroy: I don't know. I mean, I've thought about quitting playing live so many times, but every single time I would, I would still be writing songs for myself, you know?

Mike Pengra: Yeah. You said something in your bio about writing songs: "Writing is the only way I can fully express an emotion and feel like I got it out."

Ken Pomeroy: Yeah. Absolutely.

Mike Pengra: Going to the bathroom. I get that now.

Ken Pomeroy: Yeah.

Mike Pengra: Makes full sense. You also said, "I'm not writing and playing music for other people. I'm just allowing other people to witness what I'm doing for myself."

Ken Pomeroy: Yes.

Mike Pengra: Self-medication in a way.

Ken Pomeroy: Yeah, absolutely.

Mike Pengra: Yeah. Talk about your record, Cruel Joke. You've got a new one coming out in the next year as well. But I've been playing the songs from Cruel Joke, and I've been in love with them for a long time.

Ken Pomeroy: Thank you.

Mike Pengra: Talk about making that record.

Ken Pomeroy: Yeah, making that record was definitely a learning experience. I feel like it kind of started out with Dakota and I just playing really terrible local shows, and it was like we were playing in other people's bands, and it was just like — it just sucked. And one night, I remember he ... we were sitting in his car in the parking lot of of a venue that we had just played, and I say "venue" very, very lightly, but he was just like, "What if we tried to make a record of the songs that you have compiled?" Because I had so many at that point, just over the years, and I was like, "Well, OK, let's try it." And so we, you know, moved to Tulsa to finish this record, and we recorded it in a house that we were living in in Tulsa, and it was tumultuous just because of, there was another person that we were working with that just didn't really have the same vision as the two of us, and Dakota is really one of the only people that I've ever met that has just naturally the same kind of artistic vision, and we have very similar tastes in music, and he has very good ideas in the studio. So that record was definitely setting up for the next one, I think.

Mike Pengra: Which comes out next year. You've actually, you've got an EP coming out in August, right?

Ken Pomeroy: Yeah, August 20, I think. I'm not sure.

Mike Pengra: And then another record in the next — next spring, maybe.

Ken Pomeroy: Yes, yeah. I'm not quite sure what month that will be, but March, April, May. Yeah.

Mike Pengra: So how how long you've actually been touring? A touring musician?

Ken Pomeroy: I guess ... Well, it's hard because I went on my first, quote, tour when I was 16, and I went, you know, it was kind of like the Midwest, but then I played some shows. I released my first record with Horton Records, which is a nonprofit in Tulsa, and they still do really amazing things. But he really helped; like, I got to play in Europe and kind of around the the Midwest. But then I feel like once I really started touring, I was actually in a bluegrass band with Kyle Nix from the Turnpike Troubadours, and I was playing guitar and singing background with his band the 38's, and that was I think where I learned a lot, good and bad, and just witnessing, like, if I was a band leader, what I would and wouldn't do, and then Dakota and I started touring really heavily, I guess, three years ago, and it's been nonstop ever since.

Mike Pengra: How has your songwriting changed and matured as you have over the years?

Ken Pomeroy: Ooh, gosh, that's a good question. I honestly, I honestly don't know. I think it's ... I think it is, in a way, less personal.

Mike Pengra: Less personal?

Ken Pomeroy: Yeah, it's like I can separate. Instead of like putting all of my feelings out on the table, I can make it someone else's feelings and then put it on the table, kind of thing, like to where it's separated enough, because I was really struggling with playing songs that were just too personal, and I didn't want to play them every night, and I didn't want to, like, just every single night emotionally splay myself out on a, you know, a freaking platter. But yeah, I think I'm working on that, trying to like separate myself a little bit because it's a lot. It's a lot.

Mike Pengra: Kind of like writing a diary, I suppose. Get all your feelings out there at once, and, a little too personal, maybe.

Ken Pomeroy: Yep, and everybody hears it.

Mike Pengra: One of the songs you did recently was a cover of Gillian Welch's song—

Ken Pomeroy: "Look at Miss Ohio."

Mike Pengra: "Look at Miss Ohio." I just love that song.

Ken Pomeroy: Yeah.

Mike Pengra: What do you love about that one?

Ken Pomeroy: I mean, I love everything about that one. That one is also a song that I had been playing since I was you know 13, 14, 15 years old. And Gillian and David both were such a huge inspiration for me and Dakota as well.

Mike Pengra: They're the nicest people in the world.

Ken Pomeroy: I've never, like, formally met them, but we've exchanged some Instagram messages, and it makes me want to cry and throw up all at the same time. I'm such a huge fan.

Mike Pengra: Yeah. I'm really enjoying your music, and I'm looking forward to hearing your next album. What about after that? Are you going to, do you think you'd be keep on doing singing, songwriting, the rest of your life, or do you see yourself doing management or ... ?

Ken Pomeroy: No, oh, absolutely not.

Mike Pengra: Or leaving on a jet plane?

Ken Pomeroy: Yeah, I don't know. I mean, I think my only choice, really, like I said, I've tried to quit 28 times, but it always calls me back. And I honestly couldn't picture myself doing anything else. I really enjoy, you know, it's hard, but there are moments, a handful of moments, that happen that you're just like, "This is why I do this." And I wouldn't be able to get the same feeling out of, really, anything else. But I always joke that eventually, I'm gonna disappear, and no one's gonna be able to get a hold of me, and I'm gonna be, like, raising mules in the middle of nowhere.

Mike Pengra: Yeah.

Ken Pomeroy: So I don't know.

Mike Pengra: Take a moment to introduce the folks in your band.

Ken Pomeroy: Yeah, absolutely. We have Dakota McDaniel, who is my musical partner, who produced Cruel Joke and also this upcoming record, and we've been playing together for, I guess, yeah, like four years, and just been a very long journey together. And then we have Ramsey Thornton, who plays banjo and sings as well. And he has his own record. It's really great. It's called I Called It. I sang on a song of his. And then we have Cole Holleyman, who plays drums and has been a very longtime friend of Dak's. And we just got along so well that it just worked out that he was going to be in the band. And then we have Mike Rose, who I've actually known the longest. I think I met him when I was like 14 years old, and we played in a band together back in Oklahoma. And actually, I went on my first out-of-state gig with Mike.

Mike Pengra: Really?

Ken Pomeroy: Yes, playing in a band called the Flycatchers. But yeah, Mike's been bass player in many, many, many different settings of this band, so he's been the constant.

Mike Pengra: Well, ever since I've been exposed to your music, I've become a huge fan, and I wish you all the best in the future.

Ken Pomeroy: Thank you so much.

Mike Pengra: Thank you for coming back to Minnesota.

Ken Pomeroy: Absolutely, can't wait to be back again.

Video Segments

00:00:05 Days Getting Darker
00:03:49 Interview with host Mike Pengra, part 1
00:09:53 Pareidolia
00:12:11 Interview with host Mike Pengra, part 2
00:16:29 Bullseye

The first two songs appear on Ken Pomeroy's 2025 album, Cruel Joke, available on Rounder Records. Song 3 is unreleased as of this publication.

Musicians

Ken Pomeroy – vocals, guitar
Dakota McDaniel – electric guitar
Cole Holleyman – drums
Ramsey Thornton – banjo, guitar, backing vocals
Mike Rose – bass

Credits

Guest – Ken Pomeroy
Host/Producer – Mike Pengra
Video – Derek Ramirez
Audio – Evan Clark
Graphics – Natalia Toledo
Digital Producer – Luke Taylor

External Link

Ken Pomeroy – official site