Interview: Jessie Jo Dillon [2025]

Jessie Jo Dillon: “There are so many songs that never see the light of day.” Photo: Libby Danforth

It’s been another hugely successful year for one of Nashville’s most distinguished songwriters, just how does she keep it up?

Getting to the top is one thing, but staying there demands commitment and talent that very few songwriters possess. It’s having that ability to remain relevant and aware of what’s fresh without losing the unique voice that got you there in the first place, an ability that Jessie Jo Dillon has in spades, and 2025 is the latest year she’s proved it. With a whopping 35 cuts released by the likes of Russell Dickerson, Morgan Wallen, Megan Moroney, HARDY. and more this year alone, the world of country music is still crying, loving, and swaying to her tune.

Such dominance is also reflected in the many achievements she’s notched up. The reigning ACM Awards and AIMP Nashville Songwriter Of The Year, Dillon has been nominated for her third consecutive Grammy Awards nomination for Songwriter Of The Year, Non-Classical and also vied for CMA Awards Song Of The Year with Megan Moroney’s No 1 hit Am I Okay?. Among her other accolades is a highly coveted NSAI ’10 Songs I Wish I’d Written’ Award for co-penning Morgan Wallen’s Lies Lies Lies.

That she also had time to launch her label/imprint Gatsby Records, releasing Carter Faith’s equally witty and reflective debut Cherry Valley, is further testament to Dillon’s work ethic and desire to help others use their voice and tell their truth. Over a year since we last caught up with her, we felt it was time to get reacquainted…

Read our 2024 interview with Jessie Jo Dillon

Are you someone who is able to sit back and reflect on how the year has been for you from a professional point of view?

“I definitely need to spend some time doing that over the break, because it’s been so chaotic and busy that I definitely want to try to soak up some of that up. It feels like something cool happens and then you’re like, ‘Yay,’ for two seconds and then you’re on to the next thing. But it’s really important to sit in that and be proud of the things you’ve done, things you’ve worked on.”

Does your success change the way people treat you or the pressure you put on yourself?

“I think it definitely does. I’ve always been really hard on myself anyway, so that hasn’t changed. I don’t think it’ll ever change, but I definitely think people look at you sometimes like you have some kind of an answer. The funny thing about music is, if anyone tells you they have the answer, they’re lying to you. Because you never know, when you sit down to work on something. You do your best, don’t get me wrong, and once you get into the song, you sometimes know like, ‘Oh wow, we’re working on something really special.’ But for someone to say they always know how to make something a hit or to make it great, I just don’t believe in that.

“So, my process hasn’t changed. It’s just some people do think you have an answer, and I’m like, ‘Hey, man, I don’t know.’ I definitely don’t have an answer. I don’t know anyone that does.”

And does that mean you’re more protective of who you work with? Or are you still going out there to find new co-writes and artists?

“I love working with new people. I haven’t done it as much as I would like this year because I’ve definitely gotten more into a specific album. Say, Megan Moroney, who’s like a sister to me, so working with her is really easy, fun, creative, and great. I’ll spend a lot of time working on that specific project and that brings me a lot of joy. I love really getting inside a record and with the artist. I think it’s a great way to go about it, whereas seven years ago or something, I was doing that, but not to the level that I am now.

“Take Tucker [Wetmore] for instance. He’s a newer person in my world. I was texting with his manager this morning about new music and different people we should work with, things we can work on. I feel like it has definitely shifted a lot into more of that for me, it’s album-centric, if that makes sense.

“But I still write for pitch. Yesterday I wrote for pitch, but even that crew… There’s a little crew of people I have that whenever Morgan [Wallen] is looking, or thinking about looking, or just listening – because sometimes someone’s not even recording anytime soon but they’re in the mood to be listening – we’ll sit down, and he’s definitely on all of our minds.”

Will you sit together and think, ‘Okay, we want to write a song to pitch to that specific person,’ or you’ll write the best song you can and then hope it finds them?

“It’s both. You do sit down sometimes, and in all honesty, for our format, Morgan’s an inspiring person to write for, because the net feels so wide; meaning he will say things that maybe a lot of other people wouldn’t say or go somewhere sonically that maybe they wouldn’t. In that regard, he’s an exciting person to write songs for, because your ideas, the music, and the lyrics, it all feels a little limitless. I got some songs on I’m The Problem, and he’s someone I would always want to give what I deem like, ‘Oh man, this is one of my favourites I’ve done in so long,’ to. I would always want him to hear that.”

As album lovers and listeners, it’s great to hear you say that you’re writing for albums…

“Yes, me too. I think that’s why I love it so much, it’s that I’m the same as you. It feels like you’re really getting to be a part of this full story, instead of just a little vignette on track four. That gets really inspiring to me, to think about it as the whole mosaic versus just one little piece.”

Will you and someone like Megan sit down and come up with a theme for the album and write songs that take you on a journey, or is it still writing your best songs to then piece together afterwards?

“With Megan, it took us writing several songs for the theme of the record to start revealing itself. I noticed that with Brandy Clark, who is more Americana but someone I work with, you’ll write a bunch of songs and then, all of a sudden, there’s this one song that starts to feel like a North Star where you can take the rest of the record. But then, in the same breath, some songs are just fucking amazing and so you want them on the album. It has a way, the universe, God, of working itself out where these things start to all line up and go together.

How does your diary work? Are you in charge of your writing schedule, or do you have a team who go out and finds people for you?

“I do have a team, but I’m such a control freak. But I definitely have the best team. My head publisher’s name is Mike Molinar, and I have Alex [Heddle], he’s booking my calendar, and he definitely brings me things. Alex is the reason that I work with Megan. I was in his office, because I go in there a lot. We’re extremely close, and work in tandem, and are friends on top of it. He had said, ‘I want you to hear this girl. Her name is Megan Moroney.’

“He played me an early song of hers off Pistol Made Of Roses, called Fix You Too, and I just loved the song. I was like, ‘Holy shit, I definitely want to write with this girl.’ Alex is so good about bringing me things. Vincent Mason was another one, earlier this year. He heard some stuff of Vincent’s and was like, ‘You got to write with him,’ and that’s been a great relationship.

“It’s definitely a team. I definitely feel like I’m all up in it, probably at times when I shouldn’t be. I’ll text Alex at all hours of the day or night and be like, ‘So and so just texted me about this. Do you think we should do that?’ I get kind of crazy, but I think he likes it at the same time.”

It sounds like an important relationship…

“He’s so vital to me because he’ll push me. Sometimes I’ve looked at him and been like, ‘I don’t really feel like doing that,’ and he’ll be like, ‘Well, dude, you should just go in and try it.’ Sometimes he’s right, and sometimes he’s not, and sometimes I’m right, and sometimes I’m not, but I feel like I have the best shot at success having a partner like him.”

We see the huge successes that you have: the number of cuts that you get, the awards that you win… Is there still the other side where there’s just as many songs that don’t even get written, or do get written but are never heard?

“Oh yeah, for sure. But then that can be funny. I have a song that I think might come out next year. I wrote that at the beginning of this year, and it is one of my favourite songs I’ve ever written. It got recorded for a massive record, and then ended up not making the record. I was just wrecked, I cried about it.

Jessie Jo Dillon: “The only real reason I’m doing this is because I want somebody somewhere on Earth to feel like they’ve heard a song of mine and they can cry to it, drink a beer to it, or do whatever the song calls for.”

“So, I have this little song that has been this thorn in my side, and I’ll start conspiracy theory thinking, like, ‘Well, Jessie, the reason this isn’t getting cut is that you love it so much. Stop being so precious about it,’ which is probably bullshit, but I definitely get in my head about that. And it is funny, when I did start to let it go… recently it’s resurfaced and I actually heard a recording of it where it’s all of these different people on the song – like a collab. I was like, ‘Whoa, if this takes shape it’s even cooler than being on that original record.’

“Some of them do that, but even that has kind of a good story so far. There are so many songs that never see the light of day, or, I’ll shoot to get on a record and think that I’ll at least get something, and then I don’t. You do take a lot of hits. It gets different when more success starts happening because you’ve had enough time to train yourself like, ‘Okay, I’m gonna give myself an hour to be upset about this.’ I used to give myself forever to do it, but it’s like, ‘Okay, I’ve got to keep moving.’ An object in motion stays in motion – it’s that kind of energy around it.’”

We also want to talk to you about Gatsby records. Do you bring all that experience to the artists you work with?

“Oh yeah. Part of why I did the imprint… the artists, to me, they have the hardest job. I suppose they get their flowers the most, but that comes with a heavy price. A lot of them I consider very dear friends, and I’ve found over the years that they can, at times, be the least protected or thought about, because it’s such a big business.

“In doing the label, I just felt that I’m kind of like an artist protector. Carter [Faith], for instance, I’m always honest with her about certain situations. I’m always going to be like, ‘Well, X is happening because of Y. What do we want to do to get to Z?’ I always feel like the artists, the songs, and the albums are what matters the most. If I was able to have any ability to protect that and push that forward, it was the reason for me doing Gatsby.”

Will there be more music next year?

“Oh yes, I’m really excited about that. I have one artist in particular that I think I’m gonna get. We’re in deep discussions, about to get legal out and all that kind of stuff to start working on that deal. Then there’s a couple other people that I have in mind that I would really be honoured to work with.”

Is the type of artist that you’d like to sign for the label the same type of artist that you like to write for/with?

“Everyone always wants to know, ‘What’s the brand.’ In a meeting the other day I was like, ‘Honestly, I look at it like my own career. I don’t want to just work with one type of artist.’ If I think what they’re doing is fucking awesome, that’s the type artist I want to work with.

“When I was young, like 19/20 trying to get a publishing deal, I thought, ‘Man, I want to have a writing career like Bob McDill.’ He is someone I idolised, a country writer who wrote all kinds of songs. He would write a ballad like, Don’t Close Your Eyes [Keith Whitley] that just wrecked you and then his next big hit would be a bop like Baby’s Got Her Blue Jeans On [Mel McDaniel]. I always was very into that; you could have different paint brushes. So, for the label, it’s just artists that I would want to work with.

“I’ve had good success, and I feel very proud, and if I have anything to do with it, that will continue. I don’t get caught up in… for an artist that would be on Gatsby, they don’t have to write everything with me, they don’t have to use the producer that I think they should use. As long as we’re on the same page for the vision, even if we have a disagreement about a song, it’s like, ‘I don’t love this one, but you do. Well then, let’s put it on there.’ Say a record has twelve songs. To me, you need four anchors on there that everyone is like, ‘Yeah, those four songs anchor the project.’ Everything else around it is up for debate and I would want the artist to always feel heard and seen about the music they wanted to record, with whoever they wanted to make it with.”

Jessie Jo Dillon: “If I’m a betting woman, I’m gonna bet on the person that’s gonna hustle.”

Do you have also have quite clear ambitions as a songwriter?

“I got four BMI awards this year, and that was a moment for me that I definitely need to make myself sit with more. Because I was just like, ‘That’s so crazy.’ 25-year-old me would never have believed it; I was wanting to get one, much less four. You can never imagine it, and then when it actually happens, you still can’t imagine it.

“Other people say it’s imposter syndrome. I don’t know if I necessarily believe that. I think it’s what keeps people good. I think Picasso or someone said, ‘The day you believe you’re great is the day you stop being great,’ and there’s truth to that. I think everyone can own their greatness in some situations, probably more than they do. But I don’t know, like awards, it’s had me thinking, ‘Do I need to work really hard and do XYZ way to try to get BMI Songwriter of the Year?’ I mean, I never have really thought that way. Writing-wise, I just want to do really good work and write really great songs. I’m hesitant to start thinking about that too much, it’d be bad for my creativity.

“That’s something that I’m definitely realising is hard, and I’m glad we’re about to have a little time off in December. I’m very obsessed with Gatsby and doing the best I can for Carter and whoever else I’m about to work with. I think I’ve been pretty good about balancing it, but I really want to find a full centre of balancing it in the new year, time-wise. Time is very important – what you spend it doing. So, I’m not going to have the luxury as much anymore of feeling like I have all the time in the world to accomplish certain things.”

How do you how do you keep going and ensure your songwriting is still at the same standard?

“I think I’m cognizant of it every day. The part you said, of keeping the same standard. I feel very protective of that. It would be really easy, and sometimes I’m more guilty of it than others, to get caught up in shit that doesn’t matter. The only real reason I’m doing this is that I want somebody somewhere on Earth to feel like they’ve heard a song of mine and they can cry to it, drink a beer to it, or do whatever the song calls for. I have to constantly stay on high alert for when I feel like I’m getting… I love awards. Don’t get me wrong, I love getting nominated for something, or, like, I had this many songs released this year… But at the end of the day, I always want to remember that though that stuff is all awesome, the art of it all is really what matters.”

Someone in your position could get complacent and just think your name alone is enough, that you can walk into a room and not really contribute too much…

“Sometimes I wish I could, because I get so tired mentally. I’ve travelled a lot this year, all things I wanted to do, and I’m really happy to have done and continued to be doing. It does take its toll a little bit, mentally, and you can feel like a little bit of a machine. When I maybe should take a break, I’m like, ‘No, I’ve got to do this right this week, or take this meeting.’ Over the break, I’m looking forward to figuring out the best way for me to balance that.

“This is definitely a hustle business. I’ve been looking at artists for the label. One of the first things I’m even looking at is, is this person gonna hustle? So many people in Nashville, London, LA, Miami, New York… you can throw a rock and hit an extremely talented person that has really cool shit to say, or a great voice. But it also comes to me with the hustle mentality of, are you going to work really hard? Over the years, I’ve met really talented people, but the work ethic is not fully there. Sometimes it still works out, but, on the label side of things, if I’m a betting woman, I’m gonna bet on the person that’s gonna hustle.

“Especially in this day and age where there is so much noise, so much music, you just feel like, ‘Okay, what kind of song, or what kind of artist is going to cut through?’ The hustle really can play into that, and then, of course, there’s the luck factor, which I definitely believe in too. Sometimes the stars just align for something, or they don’t, and there’s no real rhyme or reason as to why that is.”

Before we end, we have to ask, how does it feel to be nominated for The Grammys’ Songwriter of the Year again?

“That was another one for me that was like, ‘What the hell?’ because this is the third year in a row. It feels so crazy to be recognised by my peers, because that’s what’s so cool about the Grammys. It is pretty much just creative-based people voting. To be recognised by a creative body in music, I just don’t know if there’s any higher compliment.

“That they’re looking at you like, ‘Man, you did some really good work,’ because, other than the fans themselves, I don’t know if there’s a better feeling. As tired as I’ve been, it’s like, ‘You did a good job this year, kid.’ The industry doesn’t tell you you’ve done a good job as much as you probably do need to hear that. So it’s moments like this that really make me be like, ‘Damn. That makes me really happy.’

If you were to look back, what would you say is your proudest moment of the year? And what is your biggest hope for next year?

“My proudest moment of the year? Wow. This Grammy nomination is definitely one, and the ACM win. I have so many proudest moments, a lot of it’s been the music really… Russell [Dickerson]’s song Happen To Me, you just don’t see that coming. We thought we were writing this fun little song, and we all loved it. But then to see how much listeners loved that song, no one saw that coming. Those moments are really cool. Anything I’ve done with Megan has meant a lot to me, too, and always will.

“In the new year, my biggest hope is to make someone like Carter Faith even bigger through Gatsby, and to be working with these artists in that capacity; to help them catch their dream and to be on a bigger stage than maybe they were this year. I feel very called to that right now, especially with her. She’s such a special and important artist. There’s this certain type of girl out there in the world that, if they heard Carter Faith, they would feel really seen. That’s really important to me, to get to as many people as possible. I’m really looking forward to doing more with that.”

You can keep up with Jessie Jo Dillon’s songwriting adventures by following her on instagram.com/jessiejodillon

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