#683 - Award-winning songwriter Jessie Jo Dillon on Bobby’s 10 Favorite Songs, the Stories Behind Them & Her Career as a Hit Songwriter

Bobby Bones Presents: The BobbyCast

Award-winning songwriter Jessie Jo Dillon joins Bobby Bones to count down her top ten favorite songs she has written, sharing intimate stories behind each hit and reflecting on

Key takeaways

• Jessie Jo Dillon is a three-time back-to-back ACM Songwriter of the Year with over 200 officially cut songs in her catalog.
• She co-wrote Megan Moroney's 'Girl in the Mirror' on their very first day meeting, a collaboration that significantly elevated both of their careers.

Main topics

• Songwriting process & collaboration stories
• Mental health, sleep struggles & work ethic

Notable quotes

"I feel like the more you've done, the more you feel... You know, so much pressure."

Conclusion

The episode offers a grounded look at the relentless discipline behind Nashvill

Transcript preview

Speaker 2 (0:00) This is an iHeart Podcast. Speaker 2 (0:02) Guaranteed human. Speaker 3 (0:11) Was that written for Morgan? When Speaker 1 (0:13) we start, we're starting the song. I don't know if we thought that. And then as we got going along, we were like, man, it would be cool if you like, like this. And then he did. And it was really awesome. Speaker 3 (0:26) Hey, everybody. I'm about to talk to one of the most successful songwriters in Nashville right now. Jessie Jo Dillon is her name. She has written huge hits for Morgan Wallen, Megan Maroney, Jelly Roll, Old Dominion, Tyler Hubbard, Maren Morris, Cole Swindell, Dan and Shay. And I could keep going, but I'd rather just get over and talk to her. And I'm going to count down my top 10 favorite songs. She's also a three-time back-to-back-to-back ACM Songwriter of the Year, which is something that no other songwriter has ever done. Rare air here. Multiple Grammy nominations. She even founded her own record label called Gatsby Records, and we'll talk about that as well. She is awesome as a person. I love having her around, and also she's a genius. Unless she's offended by being called a genius, then she just works hard. Both could be true. Here she is, Jessie Jo Dillon. You've won ACM Songwriter of the Year three times now. Speaker 1 (1:22) Pretty crazy. You helped me out one year. Speaker 3 (1:25) Not to pick you. I just went to you in the audience. No, that's what I mean though. Speaker 1 (1:29) That's like my, one of my biggest memories of that night is you're like, Hey, by the way, do you know we're doing this? And if you hadn't told me, I would have probably tripped out. So I Speaker 3 (1:40) was very grateful for you. They said, go find her. And then while you're on camera, cause this is on. Speaker 3 (1:46) Amazon Prime. Yes. Which Speaker 2 (1:47) we have to probably bleep that Speaker 3 (1:48) since we're on Netflix. But... Yeah. And so they said, go find her and just go up to her and go, congratulations. But I don't like to be ambushed. Speaker 1 (1:59) No, we're similar. I think that I'm Speaker 3 (2:01) coming up. I Speaker 1 (2:02) appreciated it. Yeah. Speaker 3 (2:03) So what I'm going to do is go through my 10 favorite songs of yours. Speaker 1 (2:07) Amazing. Speaker 3 (2:08) And then you just tell me a story. Okay. I'm not supposed to say this, but I just voted for you for song Speaker 1 (2:14) for Speaker 3 (2:15) CMAs. Speaker 1 (2:16) That's my publisher's here. He goes, let's go. That makes me happy. I have my Megan. It's the last night of the Cloud 9 tour. So thank you. That Speaker 3 (2:27) Cloud 9 did not make the list, but I love that song. I Speaker 1 (2:30) do too. Speaker 3 (2:30) Love that song. Speaker 1 (2:31) It continues to grow on me, that one. I go back to it. Speaker 3 (2:36) I went to... Speaker 3 (2:39) a couple different sites. I went to Wikipedia. I went to two DSPs and something else. And they had you at like 200 songs that are just existing. Speaker 1 (2:51) Oh gosh. I've definitely written way more than that. Which is crazy to think about. Someone asked me the other day, how many do you think you've written? Did it have been cut? Cut? I'm actually not sure. A lot. Yeah, Speaker 3 (3:03) it gave me 200 that were cut. I guess it had some sort. I'm going to look though here. Yeah. Like I went to one of them and I have 246 cut songs by artists I've heard of. That's crazy. Are there songs that are cut by you that are cut of yours that are artists I've never heard of? Speaker 1 (3:20) Probably. I feel like sometimes I'll see things on like, I don't even know what that's called. I guess just like the log of everything I've had. From the year or something. And I'll be like, who is that? I won't even know about it if it's from like another country or something, you know? But it's always a surprise in this business as we know, but. Speaker 3 (3:40) That's interesting. A song that maybe you wrote a long time ago that someone then finds and cuts and maybe they don't even live here, like Australia. Yeah, Speaker 1 (3:48) or Canada or something. And then I, speaking of that though, I had one recently that is a very old song. It's like. probably 11 years old, that me and this guy Donovan Woods wrote the first day we met that Kenny Chesney, I've been trying to get him to record it for like a decade. And he finally just put it out with Megan, actually on the new record. It's called Just Got Weird. So sometimes, I mean, they find their way, you know, it's crazy. A Speaker 3 (4:14) couple of things. I'm a Donovan Woods fan. Yes, Speaker 1 (4:16) love. Speaker 3 (4:17) As a singer, as an artist. And two, I was just talking to Kenny about that song. Really? Yeah, because... I was asking him, is there like a point? Speaker 3 (4:29) He won't go back beyond if he wrote it or if someone sends him a song. And he said, well, there's a song that's over a decade old. And it was a song that him and Megan cut of yours. Speaker 1 (4:39) Yes. So cool. I love Kenny. He's one of my favorite artists. So I've always chased. Speaker 1 (4:45) a song being recorded by him anyway. And then the story with Donovan is just so good. Like the day we met. So you can't make that up. And then that it just hung around this long. I will give Kenny, he doesn't get, he always remembers them. It may not be for this certain record. We've been talking about another song recently that he's threatened to cut a few times that I'm hoping whatever the next project is, he does. Speaker 3 (5:09) That's the kind of threat I would like. I'm threatening to cut it. Most of mine are, I'm threatening to beat you up. Or fire you. Speaker 1 (5:15) No. My threats are Speaker 3 (5:16) completely different than yours. Speaker 1 (5:17) Well, whoever those people are, I don't like them threatening you those things. Speaker 3 (5:20) Please take care of them. What's Speaker 1 (5:22) it Speaker 3 (5:22) like to just be paid for your brain? That's so cool. Speaker 1 (5:25) It's, I should ask you that too. It's weird sometimes. I'm having a weird day until I got here. So it's an honor, I think most of the time, but I think we've got to protect it. Speaker 3 (5:40) For me, sleep. and water. Speaker 1 (5:43) Yes. Speaker 3 (5:44) The very fundamental things that are easy to go, I'll catch up another day. I've now started to learn I can't perform if I don't get the main things right. Speaker 1 (5:53) The sleeping is tough. Have you had seasons where you've been struggling? Speaker 3 (5:57) All my life. Speaker 1 (5:58) Yes, me too. Speaker 3 (5:59) Yeah, all my life. I wake up two or three times a night. Me Speaker 1 (6:01) too. Speaker 3 (6:02) Like this. Here's my impression of me waking up at night. Speaker 1 (6:07) Yes. Speaker 3 (6:07) Where I go to therapy and talk about it. And it's neuro, I have crazy neurosis anyway and all of those things. But I also think that Speaker 2 (6:18) creates my superpower too. Speaker 1 (6:19) I Speaker 2 (6:19) agree. Speaker 3 (6:20) So Speaker 2 (6:21) I Speaker 3 (6:21) don't really want it to go away if it's going to affect me in other ways, but it's very difficult. Speaker 1 (6:24) It is. And I think... I don't know. I have seasons of where I just get through it. I just get through it. And then sometimes, like you're saying, it's like these certain times hit you that you're just like, whoa, this is pretty rough. I need to like take care of my brain because it is what I'm getting paid for. So I Speaker 3 (6:42) just want to do drugs. Speaker 1 (6:44) Yeah. Speaker 3 (6:44) I think that would help me relax. I can't relax. Speaker 1 (6:47) Yeah. Do you smoke weed or anything? Never once. Not once. Speaker 3 (6:50) I've never had a drink of alcohol or smoke weed. Okay, Speaker 1 (6:53) I knew that. I Speaker 3 (6:54) would love to. I would love to do them both at the same time. Yeah. One through a nostril, one through the mouth. Like I would love that. Speaker 1 (7:00) One of these days we'll do it together. I'm kidding. I Speaker 3 (7:02) don't think I can contain it if I do start it, but I would love that. I took sleeping pills for a while. And this was, I had a bunch of like personal, where people, I was getting attacked. I got jumped. I got my house broken into, like all these type things. Jeez. And so I started taking sleeping pills because I wasn't sleeping and because I was sick all the time since I wasn't sleeping. Like that's what we have to worry about. Yes. And so, but then. I would just not remember stuff the next day. Speaker 1 (7:26) I Speaker 3 (7:26) didn't know if I had my wiener on camera somewhere. I just didn't know. Speaker 1 (7:30) Well, conversation, yes. What do you want? Can I ask? Speaker 3 (7:34) It's called Edular. It's basically the same thing. I think it was probably just like a generic brand so I could save a nickel. Speaker 1 (7:41) Yes, I know. I've been debating the sleeping pill route. Now you're making me against it. Speaker 3 (7:47) I knew if I kept doing it, I would end up. doing number two in an airplane aisle and getting arrested. And I wouldn't remember any of it. Speaker 1 (7:54) Yes, I hear that, that you don't remember. Jack Nicholson, I think, has some article. He said he woke up like two miles from his house in like a golf cart. And he's like, here I am. I drove off Speaker 3 (8:04) with a gas pump in my car because it affected me so much. I went to work, was still messed up. Speaker 1 (8:10) Yeah, because then it's like that. And then I Speaker 3 (8:13) was still so messed up when I drove home. I got home with a gas pump in my car, drove off. Speaker 1 (8:17) Babe. Yeah, this isn't for me either. I don't need any more drama. I Speaker 3 (8:22) stopped. I had crazy withdrawals, Speaker 1 (8:25) but Speaker 3 (8:26) I stopped. I had to. So now I just do this at night, just constantly wake up. Speaker 1 (8:30) Magnesium, anything help? Speaker 3 (8:31) I've tried it all. Magnesium gives me like a crazy hangover. I Speaker 1 (8:35) kind of have that from it too. And then I don't feel like melatonin works for me at all. In fact, I've wondered and I've looked it up. Allegedly it can, but if it keeps me even more awake. but I'm probably just paranoid. It Speaker 3 (8:48) has that effect on some people? Speaker 1 (8:49) Yeah. The reverse? Speaker 3 (8:51) The Speaker 1 (8:51) reverse. It's weird. Speaker 3 (8:53) Basically caffeine for you then. Speaker 1 (8:55) Yeah. And it's kind of sad because this is just how we're wired. Speaker 3 (8:58) Why do you think you can't sleep? Do you think because your brain's always trying to find something? Speaker 1 (9:03) Yeah. I think always trying to find something. I think too, a friend that I write with, Jonathan Singleton, he... Works a ton with Luke Combs, amazing writer. One day, this was like a couple of years ago, actually, we were talking. I was like, I just, I don't know what it is, man. Like, I feel like I just can't stop trying to like figure whatever that day was, it out of my mind. Like, why is this being this way? And he was like, girl, we solve puzzles for a living. You're going to try to solve a puzzle about everything. Like, you just got to leave it alone sometimes. And I was like, yeah, that's true, but I don't know how. So I think, yeah, just always. It's like hamster wheel up there. Do Speaker 3 (9:42) you still have pressure to perform? Speaker 1 (9:44) Oh, yeah. Speaker 1 (9:47) Yeah. Speaker 1 (9:50) A lot, I think. Speaker 3 (9:52) Why? Speaker 1 (9:54) I don't know. I feel like it's like... I mean, you know this, Sneaky. I feel like the more you've done, the more you feel. Speaker 1 (10:06) You know, so much pressure. Speaker 3 (10:11) I'll say that and people will go, what are you talking about? But I'm saying it to you because I'm looking at somebody who's won all the awards, has all the songs and Speaker 2 (10:20) just Speaker 3 (10:21) going, man, you could just end up in a room and not have to do anything because of everything that you've done. Speaker 2 (10:25) But Speaker 3 (10:25) that doesn't matter because you didn't get to this point by having that mindset at all. That's what some of my friends will say. They're like, dude, you're here. But I didn't get here. Like what got me here is also what's not letting me relax. Speaker 3 (10:40) What do Speaker 1 (10:41) you do about it? I don't know. I Speaker 3 (10:43) have awareness of it and I just accept it. Speaker 1 (10:45) I know. I think that's all we can do, I guess. Speaker 3 (10:47) That's all I can do. And I go to therapy. I have two therapists. Well, my wife and I have one. I need to have two. And Speaker 2 (10:53) then I have Speaker 3 (10:53) one for just myself. I have a psychiatrist for the first time ever because he can actually prescribe things Speaker 1 (11:00) if Speaker 3 (11:01) needed. Speaker 1 (11:02) If needed. Yeah. Speaker 3 (11:03) And so, yeah, it's... I just know my awareness of it is that it's also allowed me really great things. Yeah. Speaker 1 (11:11) For Speaker 3 (11:11) what I, what bothers me also allows wonderful things to happen. I Speaker 1 (11:16) know. It's such a double edged, it really is this double edged sword. And it's always like. Speaker 1 (11:22) advice talking to younger people or newer people in like entertainment what we do I think it's my as much as I hate it it is my biggest advice I'm like well you just gotta outwork everybody like in certain ways like I just feel like I just have something else in me that's a little different than I think the ways maybe certain other people go about it. But like you said, it's like this blessing and this curse of it. Like no rest for the wicked, I guess. Speaker 3 (11:51) What do you think? I'm not going to tell you if you're right or not. Speaker 3 (11:55) But I've spent some days with your entire library, which I knew most of it anyway, because I'm a massive fan. Speaker 1 (12:01) Thanks. I'm a big fan of you. Speaker 3 (12:04) This is about you though. Speaker 1 (12:05) Is it? Speaker 3 (12:07) You're right. Everything's about me. Let's be honest. I love Speaker 1 (12:10) you. Speaker 3 (12:12) What do you think I would pick as my favorite song of yours? Speaker 3 (12:17) And we'll come back to it later. Speaker 1 (12:20) I feel like... Speaker 1 (12:24) Maybe that's hard because I think it depends what kind of mood you're in. But Speaker 3 (12:28) you're guessing. It's a straight guess based on what do you think I'm going to pick as my favorite number one song of yours? Speaker 1 (12:34) If it was an emo day for Bobby Bones. Every Speaker 3 (12:36) day is an emo day for Bobby Bones. That's what I mean. Every day is an emo day. So Speaker 1 (12:39) I'm going to go. Speaker 3 (12:39) Same. Speaker 1 (12:40) So I'm going to go. Maybe if it was a hit, maybe. Break up in the end? Speaker 1 (12:47) Okay. Maybe. We'll Speaker 3 (12:48) get to