The 100 Years of Radio – 100 Years of Hit Makers limited series podcast gives music fans a front-row seat for conversations with songwriters behind some of the biggest hits of yesterday and today. You’ll learn the stories behind the songs from the people who wrote them. Each episode will focus on one writer: sometimes, they’ll just talk about one song, other times, they’ll talk about a number of hits.
New episodes will be released each Monday through November of 2020.
100 Years of Radio – 100 Years of Hit Makers special podcast series is produced in partnership with Beasley Media Group, XPERI (HD Radio), and BMI in celebration of the 100-year anniversary of the first commercial radio broadcast.
This interview with Jessie Jo Dillon took place in two parts: the first was during the summer. Coincidently, it came right after her father, Dean Dillon, was announced as a new inductee into the Country Music Hall of Fame. “I don’t envy Sean Lennon,” Jessie Jo said, noting that it’s tough to live in a parental shadow. But Jessie Jo’s catalog of co-writes includes one of 2020’s biggest hits: Dan + Shay’s “10,000 Hours,” featuring Justin Bieber, among many other hits. And on the other hand, there’s the politically charged Maren Morris protest song “Better Than We F0und It,” released just a few days ago. The second part of the interview came right after the release of that song.
Her vast catalog also includes Morris’ “Rich” and “To Hell and Back,” Cole Swindell’s “Break Up In The End,” Tim McGraw’s “Here On Earth,” George Strait’s “The Breath You Take” and Brandy Clark’s “Girl Next Door,” the latter of which was based on one of Jessie Jo’s exes. She’s able to both write about the most important and controversial issues going on today — even if they are difficult to write about — and the most personal matters of the heart.
If you listen through her songs (we didn’t come close to covering all of them here), you’ll quickly realize that Jessie Jo Dillon isn’t in anyone’s shadow. In fact, her catalog casts a pretty long shadow of its own.
Let’s start by talking about Dan + Shay’s “10,000 Hours.” When did you write that?
It was the normal kind of Music Row day. I went to Jordan Reynolds’ house, who is my co-writer on it, and the guys were over. Dan and Shay were there. Dan had the title “10,000 Hours”; he liked the way it looked. And we just started talking about the adage of how you’ve mastered something if you’ve done it for 10,000 hours. I was just like, this needs to be a simple song. “Keep it simple, stupid” [laughs]. It’s a good love song. And so we wrote the song, we all loved it. And I didn’t really hear much about it for a while until I was in New York at the same time as the guys were. And Dan [Smyers] reached out to me and said, “I’ve got to see you, we’re in New York, too.”
And then so we ended up meeting up and he said, “I want to play you ‘10,000 Hours.'” And I was like, “Oh, my gosh, what? You guys recorded this?” And he said, “Yeah. Justin Bieber’s on it.” And I was like, “No way. No, he’s not.” And he said, “No, I’m serious.” And so then he dropped the headphones on my head and there’s Justin Bieber.
So what did you think when you first heard the finished version?
Oh, Brian, I cried. I mean, it was so was surreal to me. That’s one of the biggest pop stars in the world. And I’ve always loved his voice. He has an incredible voice. Being a country girl who’s written mostly country songs, it was just… very surreal, like I’m talking about someone else.
A very different song is Maren Morris’ “Better Than We Found It.” Who were the other writers? When did you write it?
Laura Veltz and Jimmy Robbins. Laura and I wrote [Morris’] “Rich” and “To Hell & Back” with Maren. Jimmy and Laura wrote “The Bones” and “I Could Use a Love Song” with Maren. We combined our powers!
Let me ask you about of the songs that you worked with Maren on, “Rich.”
I love that song so much. Maren and I had been friends but had never written a song together. And we had been drinking one night and I said, “Hey, you know, I have this idea that I’m wanting to write called ‘Rich.'” We got together with Laura Veltz. It was a really quick write.
“Rich,” lyrically, is actually a rather sad song. But we wanted it to feel fun. And it was just a really great day of three chicks, just ping-ponging melodies and lyrics back and forth. And it was one of those magical ones where it fell out in about an hour or two hours and you’re like, “Whoa, how did we just do that?”
It’s about a woman who says, “I should not get back together with this guy… but I probably will!”
Right [laughs]. Yes. Lord knows I’ve been there and I know the girls had been there, too. It’s about one of those people: you need to put them down, but you can’t! And there is a sadness in that. But and that’s why we wanted to make the production feel fun. You’re making fun of yourself a little bit, too.
What’s it like writing for, or with, Maren? She came up as a writer for other people before she started making her own records.
Right. She did. She had been a performer since she was a little girl. And so she kind of had gotten a little beaten down by that. And so when she moved to Nashville, she just thought she’d write songs [for other people]. But then she kept getting this feedback from people: “Man, I love this song, but I don’t even know who’s going to record it because you sound so great [on the demo]!”
Like “Rich,” for example, almost got recorded by somebody else. I remember she was almost done with her record. And I remember telling her, “Maren, I don’t want to hear anybody else sing this but you!”
She just has such a signature sound. She’s fun to talk about, because she’s as good as everybody thinks she is. She’s an absolute melodic force. That voice coming out of that little Polly Pocket [body]. I mean, it’s just insane. Incredible songwriter. I love writing with Mare, too, because she’s brave. She’s not afraid to do something different or sing about something that someone might tell her she shouldn’t sing about. I always look forward to our creative time together because she inspires me all the time.
It’s hard for me to imagine anybody else singing “Rich,” and when she references “Me and Diddy, drippin’ diamonds,” you have to be a certain age for that reference to even make sense.
Yes, for sure. And it actually was almost recorded by a band — and who knows if they would have ended up doing it — but they liked the song. It’s a band that I think you and I both love: Little Big Town. And I actually would have loved to hear Karen [Fairchild] sing it, but… it just felt so “Maren,” like you’re saying, with the lingo and her swoops. I’m glad it turned out how it did. But I would still love to hear Karen do it.
Talk about “To Hell and Back,” which is another big song of yours and Maren’s.
Oh, man. I love that song. I’m so proud of it. It’s an older song, actually, because me and her and Laura wrote it after her [first] record had come out. I remember she had champagne with her; we had some champagne and we’re writing “To Hell and Back.” It was a title Maren had, and she wasn’t sure what it was about. And so we did a lot of discussing about what we thought the subject matter was, and it just kind of fell out of all of us like “Rich” did. It was a very easy song, weirdly, to write, because when I listen back to it, there are parts of it where I think, “Man, how did we come up with that?” I love everything about that song. From the production to her vocal to the melodies to the lyric.
When you write songs, do you think, “This one is for Maren”? And are there songs that you guys have written with her in mind or even written with her that she hasn’t gotten around to recording yet?
Yes, we have. I have several songs with her that she hasn’t gotten to yet.
In general, if you’re sitting down with an artist, you always want to bring it. I always try to bring in hooks that I feel like might be something that the artist would be interested in singing about. With Maren, it’s easy because we like singing about the same things. Sometimes, as a songwriter, you’re matched with people and you have to kind of search for what you think would be their perspective.
Somedays you’ll think: “So-and-so is about to go in the studio [to record new material]. Maybe we could do something for them.” I feel like I never have any luck when I try to target something so hard. I don’t know if I’ve ever actually gotten a song recorded [that way]. I feel like my best stuff is always when I’m writing what feels like the best song that day, whether it’s a bop or a ballad or whatever.
Another one of your sad songs is Cole Swindell’s “Break Up In The End.” And that’s a classic song that I could imagine a lot of other people singing. But I read that a lot of people actually turned it down.
Yes. Luke Bryan had it for a while and then did not record it. And then Dan + Shay really wanted to record the song. Dan, to this day, will text me and be like, “Damn it!” because he loves that song so much.
But Cole put it on “hold” for us. And he’s a very dear friend. And I think he did a great job with that. Even though he’s not a songwriter on it, that song was very personal to him because he had just gone through a breakup that had quite devastated him. And that’s the beauty of professional songwriting: when the songs find this home, and they take on this whole other thing because the singer has just bonded with it so much.
Dan + Shay can still cover it!
I would love to hear that, actually.
I think that’s the kind of song that everyone could bring their own thing to. And it would sound great by almost anybody.
Gosh, I hope so… it feels like that kind of song to me. It feels weird to say that about your own work [laughs]. But I’m just so proud of that song.
[When we wrote it] It was another easy day. I had that title, I had seen this book called John Dies at the End in the library. I thought, “Man, I want to read that. How does he die?” And I thought, “That be a great way to write a song where the title just gives it away.” Originally, we [Dillon and co-writers Jon Nite and Chase McGill] were calling it “We Break Up in the End.”
When I brought that into the guys, I was thinking, “They’re either going to think this is crazy or they’re going to like it,” and they both loved it. And the rest is history, I guess.
You mentioned that Luke Bryan had it on “hold.” What’s it like for you when you write a song, and it’s sort of in the clutches of a huge artist or their manager?
It’s torture [laughs]!
How does it how long does that last? And what goes through your mind?
Oh, man. You always hope it’s short, because Lord, it can be long. I mean, I’ve had songs that have been held for almost a year. You know, I’ve had songs that have been held more times than I have, to be honest [laughs]! And they still somehow have managed to not make it to a record.
I feel like “holds” make you feel good for the first 30 minutes. You’re like, “Heck, yes! We have a chance.” And then, in comes the doubt. “I wonder if so-and-so is going to knock this off the record.” I’ve had to learn in my career… I used to get so upset. I’d be lying if I said I still didn’t get upset sometimes. When I had a song held for a long time and it and then it didn’t get recorded, I used to always take it so personally. And I’ve realized through working with more artists as I’ve gotten older and been in the field longer, that sometimes they love a song and they go in to record it and it doesn’t sound right. It doesn’t fit the record. It doesn’t sit in their voice. And that’s OK. It doesn’t mean the song is bad. It just, unfortunately, didn’t work.
Let’s talk about Tim McGraw’s “Here On Earth.” Writing a song for a star of that stature must have been really thrilling.
Oh, it’s insane. I mean, I fell asleep when I was a little girl every night listening to Tim’s “Everywhere” record. My brothers and I had bedrooms across the hall and my mom put a boombox in the middle of the hallway and on and put on the CD… or it might have been a tape. And we would just fall asleep listening to it. Tim’s body of work is unparalleled to me. He’s one of my favorites in our genre.
We actually wrote that song at a writing camp for him. Missi Gallimore, who works with him, does A&R for him and her husband, Byron, who produces him, set up a camp with some writers to try to target [songs for] Tim. And I remember that they asked that day… I can’t remember what song it was, but they were like, “Tim’s really loving this song.” It was a classic-rock-like tempo. And he wanted thing in that vein. And Chase and Jon and I — we just all kind of looked at each other and were like, “Yeah, we kind of don’t know how to do that. We just need to write a great song today and see what happens, you know?”
And that was “Here on Earth.” It was Jon’s idea. Once again, it was a fairly easy day of great co-writing where nobody’s that odds and everybody’s on the same page. And it felt like a special song in the moment. I know it means so much to both of them, but especially Chase. When he first heard Tim’s version, he sent me a long text and was like “Having my daughters now and hearing Tim McGraw sing this song just brings me to tears because it just makes me think of my girls.” That’s been such a cool, insane thing.
I love Brandy Clark’s “Girl Next Door,” and I love the line, “If you want the ‘girl next door,’ go next door!”
I will never forget this: I standing on my porch. I was dating a guy at the time and I was livid at him. And I said to her on the phone, “If he wants to the girl next door, he needs to freakin’ go next door.” And she was like, “Jesse, you need to come over right now. You need to write that song.”
We also called Shane McAnally, who’s both of our good friend and an amazing, amazing, amazing songwriter. And we told him the idea and he was like, “Can y’all just come over now?”
We went over to Shane’s and we wrote that song. I remember that was one that took longer. We were deciding on, very specifically, exactly what we wanted to say. We had so many options because it was such a fun song to write, that it was almost like whittling them down.
I want to ask about the processes of writing “The Breath You Take” for George Strait. That’s a song you wrote with your father, who just got into the Country Hall Of Fame [Dean Dillon]. That’s a song that has a very parenteral narrative to it.
Yes, it does. It was one of the first songs I wrote with my dad. Growing up the daughter of a Hall of Fame songwriter is an interesting road. I do not envy people like Sean Lennon at all, because you’re definitely in a shadow. You’re a bit in awe of your parent. I definitely am, still to this day, in awe of my dad. At first, I was very quiet with him about the fact that I was writing songs.
And I remember he was kind of annoyed with me: he was like, “Why haven’t you been sharing any of this with me?” I think I was just nervous. And I remember I had a sketch of an idea for the chorus of “The Breath You Take.” And I called my dad and sang some of it to him and sang some of the ideas I had. He was like, “Well, I’m writing with Casey Beathard today. Will you just come over and let’s write the song?” And so I did… with these two huge juggernauts. Casey Beathard has written for Eric Church and Kenny Chesney and all kinds of amazing artists.
But it was another one that was an easy song. I feel like all of us knew what we wanted it to be. Sometimes in co-writes, I think sometimes people can be on a different page and sometimes the song can still work out, but then sometimes it doesn’t because you can just never really agree.
So it was just one that still means a lot to me, and I know it means a lot to Casey and my dad. I think we got to say something that we wouldn’t have said if it wasn’t in a song.
Is it hard to write with your father?
I really enjoy writing with my dad. Writing with him and another writer is always funny and fun because I can watch the other person be in awe of him and sometimes I have to be the one to say, “I don’t know, Dad… I don’t think that’s it.” And you can watch the other person look at me like “What?” But, you know, Dad’s not always right. He knows.
What other songs do you want to discuss?
I have two songs that came out on Lindsay Ell’s album [Heart Theory]. I’m really proud of her, she really dug in. And I think she made a record for herself; it is the record she’s always wanted to make. I’m very proud of her and I’m really proud to have songs on there. My songs are called “Ready to Love” and “The Other Side.”
It’s a cool record in that way because it really does go through the stages of grief. I think she did a great job of doing that. I mean, having gone through breakups myself, man: what different emotions you feel over the course of six months or so. If not longer, if you’re me! Lord, I’ll hang on to anything! For too long! But so I am excited about those songs.
And then I have also been excited for Brett Eldridge’s album. Similarly to Lindsay, he just made a record [Sunday Drive] he had always wanted to make. And I think he kind of changed courses a bit for himself, and I think that was a hard decision for him to come to, but it was one that felt right in his heart. And so it was very, very, very awesome to be a part of that project for him. My songs on there are called “Where The Heart Is” and “The One You Need.”
You mentioned that you would never want to be a recording artist. So what is next for you? Do you not have the ambition to make your own record of yourself?
I have always said that… and lately because of COVID, I have found myself thinking about that. Just making an album for myself, really, because as a professional songwriter, you write so many songs that you love that don’t ever get recorded and no one ever hears them.
I understand the trend that happened a few years ago — and it’s still happening now — where great songwriters that are also singers say, “Screw it, I’m gonna make a record,” like Maren Morris or Michael Hardy [aka Hardy], Old Dominion, Brandy Clark. You’ve seen a lot of great artists come out of Nashville who were originally songwriters making records, because I think they want their music to get out. And so I found myself sitting a little bit in that. And I’ve had a few baby conversations with my friend who’s a producer-songwriter, Aaron Eshuis, because if I was ever to do something, I think I would want to do it with him because he’s so easy for me to be around. And it would just be a full-on exploration. Who knows if I’ll ever actually do it. But I have been thinking about it a bit.