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

0:07 Was that written for morgan when 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'd be cool if you like like this and then he did and it was really awesome.

0:21 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.

0:41 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.

0:53 Rare air here. Multiple Grammy nominations.

0:56 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.

1:18 Pretty crazy. You helped me out one year.

1:21 Not to pick you. I just went to you in the audience.

1:23 No, that's what I mean, though.

1:25 That's like one of my biggest memories of that night. 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 was very grateful for you.

1:36 They said, go find her. And then while you're on camera, because this is on Amazon Prime.

1:42 Yes.

1:43 Which we have to probably bleep that since we're on Netflix. But- And so they said, go find her and just go up to her and go, congratulations. But I don't like to be ambushed.

1:54 No.

1:55 We're similar, I think.

1:57 I'm coming up.

1:57 I appreciated it.

1:59 Yeah. So what I'm going to do is go through my 10 favorite songs of yours.

2:03 Amazing.

2:04 And then you just tell me a story.

2:05 Okay.

2:06 I'm not supposed to say this, but I just voted for you for song for CMAs.

2:11 That's good. My publisher's here. He goes, let's go. That makes me happy. I have my Megan.

2:18 It's the last night of the Cloud9 tour. So thank you.

2:23 Cloud9 did not make the list, but I love that song.

2:25 I do too.

2:26 Love that song.

2:27 It continues to grow on me, that one. I go back to it.

2:32 I went to a couple different sites. I went to Wikipedia.

2:38 I went to DSPs and something else. And they had you at like 200 songs that are just existing songs.

2:47 Oh, gosh.

2:49 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?

2:54 That have been cut?

2:56 Cut? I'm actually not sure. A lot.

2:59 Yeah.

2:59 It gave me 200 that were cut. I guess it had some sort. I'm going to look though here.

3:03 Yeah.

3:03 Like I went to one of them and.

3:05 I have 246 cut songs by artists I've heard of.

3:09 That's crazy.

3:11 Are there songs that are cut by you that are cut of yours that are artists I've never heard of?

3:16 Probably.

3:16 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.

3:26 And I'll be like, who is that? I won't even know about it if.

3:29 It's from like another country or something, you know. But it's always a surprise in this business, as we know.

3:36 That's interesting.

3:37 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?

3:43 Yeah, or Canada or something.

3:45 And then, 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.

4:10 A couple things I'm a Donovan Woods fan yes me love 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 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.

4:34 Yes.

4:35 So cool.

4:36 I love Kenny. He's one of my favorite artists. So I've always chased 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.

4:51 I will give Kenny. He doesn't.

4:54 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. 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. No.

5:11 My threats are completely different than yours.

5:13 Well, whoever those people are, I don't like them threatening you those things.

5:16 Thank you.

5:16 Please take care of them. I will. What's it like to just be paid for your brain? That's so cool.

5:21 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.

5:36 For me, sleep and water, the very fundamental things that are easy to go, oh, 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.

5:49 The sleeping is tough. Have you had seasons where you've been struggling?

5:53 All my life.

5:54 Yes, me too.

5:55 Yeah, all my life. I wake up two or three times a night.

5:57 Me too.

5:58 Like this. Here's my impression of me waking up at night.

6:03 Yes.

6:03 Where I go to therapy and talk about it.

6:05 Yeah.

6:06 And it's neuro. I have crazy neurosis anyway and all of those things, but I also think that creates my superpower too.

6:15 I agree.

6:16 So I don't really want it to go away if it's going to affect me in other ways, but it's very difficult.

6:20 It is.

6:21 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.

6:37 I just want to do drugs.

6:40 Yeah.

6:40 Yeah. I think that would help me relax. I can't relax.

6:43 Yeah. Do you smoke weed or anything?

6:44 Never once.

6:45 Not once?

6:46 I've never had a drink of alcohol or smoked weed.

6:48 Okay, I knew that.

6:49 I would love to. I would love to do them both at the same time.

6:52 Yeah.

6:52 One through a nostril, one through the mouth. Like, I would love that.

6:56 One of these days, we'll do it together.

6:57 I'm kidding.

6:58 I 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 These type things.

7:10 Jeez.

7:11 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.

7:15 Like, that's what we have to worry about.

7:16 Yes.

7:17 And so... But then I would just not remember stuff the next day.

7:21 Mm-hmm. I didn't know if I had my wiener on camera somewhere. I just didn't know.

7:25 Well, conversation, yes.

7:26 Yes.

7:27 What do you want?

7:28 Can I ask?

7:28 You can ask whatever you want. It's called Edular.

7:31 Okay, I've heard of that.

7:32 It's basically the same thing. Okay. I think it was probably just like a generic brand so I could save a nickel.

7:37 Yes. I know.

7:38 I've been.

7:39 debating the sleeping pill route. Now you're making me against it.

7:43 I knew if I kept doing it, I would end up doing number two in an airplane aisle and getting arrested.

7:49 And I wouldn't remember any of it.

7:50 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.

7:59 I drove off with a gas pump in my car because it affected me so much.

8:04 I went to work, was still messed up.

8:06 Yeah, because then it's like that's still in the system.

8:08 And then I was still so messed up when I drove home. I got home with a gas pump in my car, drove off.

8:13 Babe.

8:14 Yeah, this isn't for me either. I don't need any more drama.

8:18 I stopped.

8:19 I had crazy withdrawals, but I stopped.

8:22 I had to. So now I just do this at night and just constantly wake up.

8:26 Magnesium, anything help?

8:27 I've tried it all. Me too. Magnesium gives me like a crazy hangover.

8:31 I 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.

8:44 Has that effect on some people?

8:45 Yeah.

8:46 The reverse?

8:46 The reverse. It's weird.

8:49 It's like caffeine for you then.

8:51 Yeah.

8:51 And it kind of sucks because this is just how we're wired.

8:54 Why do you think you can't sleep? Do you think because your brain's always trying to find something? Yeah.

9:00 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 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.

9:22 Like, why is this being this way?

9:23 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.

9:38 Do you still have pressure to perform?

9:40 Oh, yeah.

9:43 Yeah.

9:46 A lot, I think.

9:48 Why?

9:49 I don't know.

9:51 I feel like it's like, I mean, you know this, Sneaky. I feel like the more you've done, the more you... feel, you know, so much pressure.

10:07 I'll say that and people will go, what are you talking about? And I'm saying it to you because I'm looking at somebody who's won all the awards, has all the, all the songs and just going, man, you could just, end up in a room and not have to do anything because of everything that you've done. But that doesn't matter because you didn't get to this point by having that mindset at all. Right.

10:26 That's what some of my friends will say.

10:27 They're like, well, dude, you're here.

10:29 Right.

10:30 But I didn't get here. Like what got me here is also what's not letting me relax.

10:35 Right. What do you do about it? I don't know.

10:38 I have awareness of it and I just accept it.

10:41 I know. I think that's all we can do, I guess.

10:43 That's all I can do. And I go to therapy. I have two therapists. Well, my wife and I have one.

10:47 I need them too.

10:48 And then I have one for just myself.

10:51 I have a psychiatrist for the first time ever because he can actually prescribe things if needed.

10:57 If needed.

10:58 Yeah.

10:59 And so, yeah, I just know my awareness of it is that it's also allowed me really great things for what bothers me. also allows wonderful things to happen.

11:11 I know. It's such a double-edged, it really is this double-edged sword.

11:15 And it's always, like, 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 got to 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 way... 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.

11:46 I guess.

11:47 What do you think? And I'm not going to tell you if you're right or not. But I've spent some days with your entire library, which I knew most of it anyway.

11:55 Because I'm a massive fan. Dang.

11:58 I'm a big fan of you.

12:00 This is about you, though.

12:01 Is it?

12:02 You're right. Everything's about me. Let's be honest.

12:05 No!

12:05 I'm fucking kidding. Let's be honest.

12:06 I love you.

12:08 What do you think I would pick as my favorite song of yours? And we'll come back to it later.

12:14 I feel like.

12:20 Maybe that's hard because I think it depends what kind of mood you're in.

12:23 But you're guessing.

12:24 It's a straight guess based on what do you think I'm going to pick as my favorite number one song of yours?

12:30 If it was an emo day for Bobby Bones.

12:32 Every day's an emo day for Bobby Bones.

12:33 That's what I mean.

12:34 Every day's an emo day. So I'm going to go.

12:35 Same.

12:36 So I'm going to go.

12:37 Maybe if it was a hit, maybe Break Up in the End.

12:41 Okay.

12:43 Maybe.

12:43 We'll get to it. Let's see what we got here. At number 10 of my favorite songs of yours.

12:49 Break Up in the End. Girl in the Mirror. Megan Maroney. Oh, thank you.

12:55 Dude, I... Love that song. The first day that we met, we wrote that. Wow.

13:02 Yes, literally.

13:03 And it was so crazy because my publisher, Alex, is here. I have to always give hats off to him because he was a fan of her before I was. He had been saying, dude, you've got to listen to this girl. You've got to listen to her. She's so good. And then she has that Pistol Made of Roses EP, and I remember one day because— Music can be hard, like writing all the time or whatever.

13:29 I get in moods.

13:29 I don't want to hear music at all. So sometimes I have to make myself sit down and listen. And I was sitting listening to that EP and I just fell in love with her voice. And the writing is what I was so struck by. Anyway, we like get together at Shane McAnally's building for Smack. I'll never forget.

13:48 And we just like hit it off immediately. And kind of just, she had that idea for that song. And I think we both related to it so much. And I'll just never forget that day because I feel like it was such a big change in my career.

14:09 Getting to meet her.

14:10 And I think a little bit for her too, you know, like one of those writing relationships you know exist, but you hope you find. And it definitely was like a monumental day for me looking back, you know.

14:24 I'm such a fan. I've said for a long time about her. I think she's my favorite writing artist.

14:29 Agree.

14:30 I agree.

14:31 She has such a unique perspective, you know, and we were just in Stockholm.

14:38 She is amazing. over in Europe for Cloud9. Tonight's the last night.

14:42 But working with some new people and I just, I was sitting there watching her like as we're in this room and I was like, man, Meg always, she's just going to hold her own. She knows who she is and what she wants to say. She's a great collaborator at the same time. Like I feel like we have such a good workflow of the both of us, but she's just such a great writer.

15:09 I love how it starts just raw and it's the girl in the mirror. She's lost her mind. She has gotten too used to crying all the time. Like that sets up. It's so simple, but it's so like complex.

15:25 I made a word up here. It's complexly simple.

15:27 Yes, I'm with you because I think it just kind of is disarming too. You're like, bam. And I've always loved simple. fuller even though like you said it is complex because like Willie Nelson is someone who's always been great at that to me like he's very cuts to the heart of the matter but it just.

15:49 He doesn't have to put a bunch of shit around.

15:51 It to make you feel and I think Megan my dad is like that honestly too I think Megan for sure and that song just even makes me want to go listen to it actually I haven't listened to her in a second.

16:06 And number nine Lies, lies, lies, Morgan Wallen.

16:09 Love. Another like, another song. I love Morgan's voice. It's one of my most favorite.

16:18 Kind of, he's a.

16:19 Top vocal for me of anyone. There's something about it. Like you just always, it's an emotional vocal and that's another like pivotal song because this group of us, it's me, Chris Tompkins, Josh Miller, Daniel Ross. It was kind of the first day we had all been set up to write together. And it turned into this, we call it like Lies Crew now from the song. But we spent a lot of time working together for that past record of Morgan's. And that song came from like a very real place. And I just, it will always be one of my favorite cuts. I think I've, I love the way he, I love the artwork with like the tattoo, um, everything about it.

17:07 Was that written for Morgan?

17:09 You know, in a way, but no, like we, when we start, we're starting the song. I don't know if we thought that. And then as we got going along, I think it was a little bit of different, like for instance, the demo, it has no drums. It's just acoustic, very, uh, different than what, um, Mo and, and Joey had kind of been doing at the time and Charlie. And so as we got going in it though, we were like, man.

17:41 It'd be cool if you like, like this. And then he did. And it was, it was really awesome.

17:46 Yeah.

17:47 And it kicked off this whole season of us trying to write so much for him during that time.

17:55 If Morgan picks a song and cuts it, That's got to feel great.

17:58 But then also you're up against 72 other songs on the same album and you're going, what's going to be a single?

18:02 The odds of being a single are one in a hundred.

18:04 That was the other part that was crazy is it was very early on in him working on that record. And I think he gravitated to the song so much that I feel like if I'm remembering right, no sleep. It's hard. He kind of early on, they were Seth England at Big Loud. Everyone was kind of like, wow, we want this to be a single. And they kind of saw it through. So it didn't feel quite as competitive.

18:33 In that record process yet. I mean, it always is. Don't get me wrong.

18:36 But yeah, towards the tail end of it, it gets extra like, who's going to get the songs on there?

18:43 Who's going to get the singles?

18:45 Let's take a quick pause for a message from our sponsor.

18:57 And we're back on the Bobbycast.

19:00 Do they ever tell you, not this group or any group specifically, but yep, it's a single and then it ends up never being a single?

19:06 Oh, yeah.

19:08 All the time. It's brutal.

19:10 The worst, I will say, almost, I was going to be like, yeah, right. But worse than that is when a song gets recorded for a record and you're so... stoked and then it doesn't even make the record you're like what um that's devastated me a couple times like just when I think something can't even really upset me in this business anymore like a song I love like that happened last year about something that I was like what and um yeah it's painful.

19:38 Has it ever happened where it found another place though like another home yes.

19:42 Um hopefully actually the song I'm thinking of might have found another home I need to check up on that, actually.

19:50 But, yeah, they do sometimes.

19:52 Is there a curse of if you cut a song and they name the tour after it, you know it's not going to be the single?

19:56 You know, I think that happens a lot, actually.

20:00 My dad swears he's had an experience where someone did– This is the worst version.

20:05 Cut this song for a record, named their tour that, and then it didn't even make the record, and they still did the tour. That's crazy. Brutal.

20:15 It feels like any tour that's named after a song, that song is never a single or is never a hit.

20:20 That is so true. It's so true.

20:23 At number eight, 10,000 Hours, Dan and Shay and Bieber.

20:29 Just nuts.

20:30 I mean... I just, Dan, he surprised me with that. It's such a good memory. Like we were in New York and he, Alex and I were together. And then he, Dan and Shay were like, you've got to meet up with us. We've got to play you something. And I thought, oh man, I wonder if they did that 10,000 hours that we wrote. And cause we're all good friends, like outside of work even. And Dan was like, Justin Bieber's on this. I was like, no, he's not.

20:58 No, he's not.

20:59 Yes, he is.

20:59 Finally just put, the headphones on and like cried, did the whole thing. But cause I mean, Justin's like a otherworldly level person and to get to have a song that wasn't his norm, you know, that he, um, liked enough to, to be on it. It was just such an honor. And, and then I I'll never forget. They did that performance of it at the Hollywood bowl. Um, I feel like it was like COVID times or something.

21:25 Cause I think it was empty. Um, but I, I always like see them, And that performance in my head.

21:32 And number seven, Cole Swindell, Break Up in the End.

21:34 Damn. I was wrong.

21:36 It made the top ten.

21:37 Okay, that's good. If it didn't at all, it'd be bad. Man, love that song too.

21:44 Love Cole.

21:44 He's an old friend. Chase McGill and John Knight. We've done a lot of songs together too. Two of the best songwriters I know. And something is happening with this song lately because I've seen a couple people post it. Lately, just random people and then different artists, friends. Like I had someone bring it up the other day being like, man, I love that song.

22:08 We should do something like that. And I was like, oh, wow, it's still got some magic in it. I love that.

22:15 I'm really proud of that song. Again, it's simple, but I think it just kind of hits, you know.

22:22 Do you remember all these songs or do you have to remind yourself of where you were because you know you're going to get asked about them?

22:28 I remember what's everywhere I was.

22:30 Like I remember that day I was in Universal Publishing because Chase has kind of like a room he always writes at in there.

22:39 And it was another first.

22:42 Like I think it was maybe the first time we worked with John Knight because Chase and I have long worked together a lot. And I remember that day like very vividly. Most of them I do remember things.

22:58 Think I would just make up stories and then call my other writers and go I said this because you have so many.

23:03 Well some of them you have to be like well this is kind of boring I mean so I got to make something up maybe but then I usually don't but.

23:10 Like cover me here's my story I just told in an interview yeah if anyone asks we were on a Ferris wheel we were like it'd be something it'd be something like that yeah.

23:18 I bet somebody has that story actually songs come the craziest places.

23:23 And number six, I have a song, and I'm not sure your relationship with songs that became massive hits because of the virality of the song, but I have Russell Dickerson, Happen to Me.

23:33 Love.

23:33 I love Russell. He's such a great guy.

23:36 Love Russell. And I think the song is really good.

23:38 I think that song, though, exploded because of all the extra effort through it going viral and them doing the dances.

23:46 Oh, totally.

23:47 Yes. I mean, it's such a nowadays song.

23:50 Yeah.

23:51 Where you can't make it up, some of it.

23:52 You know, it's like, You go out and try— the artists, I mean, they have to do so much to— there's so much, like, noise anymore, you know? But Russell, I mean, yeah, the dance, everything. And that was a really fun day. Like, again, we're all lucky that you get to work with people you have fun with, like, 98% of the time. So— I remember that song kind of just fell out too, like they do. Sometimes it wasn't hard day. In fact, I think we wrote two songs that day. I think the other was a ballad. And then we kind of got into Happen to Me.

24:36 But yeah, love.

24:39 You're right. Artists have to do a lot more than they did even five years ago.

24:42 Oh, it's crazy. I feel for them every second of the day, really. It's a lot.

24:48 And him committing to that bit.

24:51 Yeah.

24:52 And the bit wasn't working at first because no bit works at first. Nothing works at first. And I just remember him doing it and doing it and doing it. And then it slowly started to build and he would go to more places and get people to do it.

25:05 And then, womp.

25:07 It's so crazy, you know. And that, in this day and age, I feel like too... getting a little bit in this newer part of my life on like more of the business side of things a little bit too. I think it's kind of Wizard of Oz. Like you're expecting one of these guys to know something. And you're like, oh, wait, shit.

25:28 I don't know if anybody knows. I had one of them tell me the other day, you know how that song was big? We opened the window.

25:33 And I was like, wait, you're supposed to know more than that, right?

25:38 And I think it is the over and over and over because I saw something of Alex Warren- like a few months ago at Ordinary, he said that he just kept going.

25:47 And he was in this book talk or whatever. And then one day it just, and Russell, same thing with the dance.

25:53 And, you know, I think it's, I feel for them because there's no way that doesn't get old, even if you like the dance, which who doesn't? But I'm sure, you know, it's like sometimes he's like, I don't want to have to pose this again, but he sure did.

26:07 Number five, Old Dominion, Memory Lane.

26:09 Love.

26:10 I love it too.

26:11 Oh, thanks, Bob.

26:12 Well, I love all these.

26:13 Yeah.

26:13 And I'm going to love them more as we go, by the way. So it's going to be me loving them. As we go, it's going to build. Okay.

26:19 Yeah, just so we know.

26:21 But then I had gone through a really bad breakup. I remember that.

26:25 I remember we were at Brad's house.

26:28 And I've known those guys for so long.

26:32 It's like family or something.

26:34 And I remember Brad had this, like, which we usually, that crew of us, this is making me think songs are just funny how they happen. He had this like loop, kind of this drum thing because they wanted to do a more rolling kind of thing, which, and we didn't even really use it in a demo or anything. I don't think it was just more being like conscious of it in the room. And we just got on that.

27:01 Matt was like, I saw him say it was my idea. I don't really remember that, but I guess I'll take it, I think.

27:08 Maybe it was. I don't know.

27:10 But, yeah, good heartbreak song. It doesn't sound that sad, which I like songs like that.

27:17 Songs that trick you into being sad?

27:19 Yes.

27:20 You know, where lyrically it's pretty sad, but then John Mayer is great at that, I think, always has been, where they don't sonically sound super sad, but they are.

27:32 I saw a clip that went viral again of John Mayer, and I was in the clip, but I had John Mayer.

27:38 I just saw it last night.

27:39 You did?

27:39 Someone else posted it, yeah, and it had like a million views. See, again, internet's so weird.

27:42 I know.

27:42 Viral again. You're like, okay.

27:44 And I asked John Mayer what song does he hate playing, and he said, well, what do you think he said?

27:50 Slow Dancing in a Burning Room?

27:51 Waiting on the World to Change.

27:52 Yeah.

27:54 And we got into this whole discussion, and I have never really watched this interview back fully, and it was just a clip.

27:59 Uh-huh.

28:00 On that, because I was really writing a lot of jokes at the time.

28:03 I was just starting doing stand-up, and I felt like some of the stuff that I was writing was so just low hanging fruit down the middle.

28:11 But then I would notice people would laugh the hardest at that. And he said, that's how his songs were.

28:14 Sometimes he felt like the songs that he put, put no effort into were the ones, were the ones that resonated with folks.

28:20 Wow.

28:21 Interest.

28:21 Yeah.

28:22 And that he had to do kind of a shift to go, wait a minute.

28:25 He's challenging. He's trying to challenge himself. And he thinks the more that he challenges himself, the better the song is going to be. When in reality, it's kind of the stuff that just fell out of him. So he feels like people are celebrating his, stuff that he didn't have to work that hard on so he doesn't feel like he deserves it.

28:37 That completely makes sense to me, 100%. I'm like, I think, yeah. Because that is true. Because some of them do just fall out. I don't fully subscribe, though, because I hear people say it a lot. Like, hey, man, if that didn't just fall out in like one or two hours, then it must not mean it's a great song or that it's going to do something. I definitely think a lot of the time that's true, which.

29:03 For John, I'm like, I hate that he.

29:05 But I get what he means, that you feel like you don't deserve it as much. Or ones you can like slave over to.

29:11 Yeah, you feel like you deserve it because you put in all this work.

29:14 Yeah, and you challenge yourself to his point because that gets harder to do the more you go along.

29:22 You know.

29:23 Yeah, and his point was, this is just kind of down the middle.

29:26 I'm just like saying stuff that everybody feels, like very populist, like keep waiting, waiting for the world to change.

29:33 And he's like, I just don't want to.

29:34 And it feels good, you know.

29:36 Do you ever have a song?

29:40 That you do slave and maybe you don't finish and you come back to it multiple times, you can't quite get it? Will you stay with that song or will you just let it go eventually?

29:47 If it's an idea for something I really love or if it's come from like a super real place for me, I'll probably keep trying to go back to it.

29:55 I mean, I wrote a song....

29:59 Recently, that was an idea I had that I know eventually within the next year I'm going to text who I did it with and be like, hey, I'm going to rewrite this with someone else because I don't think it's going to make the record. So yeah, some of them I just can't let them go.

30:17 Do you have any songs that did well for you that took you multiple sessions to write?

30:23 Yes, I definitely have had songs that... I was just talking to someone about this the other day. Dang. Now it's going to leave my mind, of course. There was one I was like, well, we worked on that multiple times. And they were like, yeah, we did. And now I can't think. I'll think of it. It could be one of the.

30:47 Four I have left.

30:48 I know. I wonder.

30:50 The Bobbycast. We'll be right back. This is the Bobbycast.

31:05 And number four, Friday Night Heartbreaker, John Party.

31:11 Dude, I love that you say this song. I love that song so much, too.

31:16 I love that song so much. That song makes me feel good.

31:19 That makes me happy because we base so much of that song around, like, the musicality of it, like the guitars and everything. And I fucking love Jay Joyce and John. And so it was just such an honor to, like, get... I just loved... I've known John forever, so I loved that it was this record he was doing with Jay.

31:40 And I liked that John... They had to wrangle that song. I remember there was kind of some things that had to get figured out.

31:47 But then, yeah. And then I love hearing it live.

31:52 It's like a live song even like musically and stuff.

31:56 I feel like it screams John too.

31:59 Yes.

32:00 Like sometimes a song just deserves to be with a specific artist.

32:04 Totally.

32:04 Totally.

32:05 And a lot of artists could have done that song justice, but that song to me just feels like it found the right person to sing that song.

32:11 Totally. And if I remember right, I think we thought of John when we were writing it. So that's always, because sometimes you'll think of them and they're like, you know, when they actually hear it. But when you do think of them and one of them is like, yeah, it's a really good feeling, you know.

32:29 I'm going to go back a little bit for this one. What do you think number one is now? We only have three left.

32:35 Is it unsuspecting?

32:41 A little? A little, but not for the reason you're probably thinking.

32:45 And I don't want to lead the witness here, but I think if I were to show everybody all of your songs, I don't think anybody would think I would pick this song, but it makes sense.

33:03 I don't want to say one and then not be on here because I have one in my head now that I will forget is one of my favorite songs.

33:09 This is personal taste.

33:11 I had a song with Maren.

33:12 Morris called Hell and Back that I really love that I, not I forget about it, but it was just, it didn't go like crazy high on something I don't think if memory serves. And so I'm like, it's probably like that song randomly, but now I'm like, no.

33:30 I don't know. Coincidentally, it is a Maren Morris song.

33:34 Okay.

33:35 So.

33:36 At number three, not at number one. It's rich, yeah.

33:38 Okay, love.

33:39 Rich, too. Well, then, that got set up well, then. Ha-ha.

33:43 You would think we planned that. I know.

33:45 We didn't, guys. Promise.

33:46 That feels like that song was 100 years ago and yesterday at the same time.

33:50 It does.

33:50 I used to listen to that song. I had a playlist. Every time I'd go out and do a. Theater, like a comedy show.

33:56 I had like three songs I listened to every night before I went out just to kind of put me in the same spot.

34:01 And this was one of them.

34:02 And so when I hear that song, I think about just where I was all those nights because I tried to build in repetition and like have this habitual thing that I would do before I would go on stage. So I'd be in the same place every time. And that song is one of them. I wrote about it in one of my books because I was just talking about how I just tried to be the same performer every night, and I would do the same things. I would eat the same thing, listen to the same music.

34:22 And this was one of the songs, so when I hear it and was listening back to your music, it just kind of put me back there.

34:26 Do you feel like that worked, the repetition?

34:29 I think I'm so all over the place and scattered that I think it definitely contained it a bit.

34:35 Okay, this is inspiring me to try to do something like it.

34:39 Because I just, if I could do the same thing over and over again, I could at least somewhat be dancing on the same dance floor, I felt like.

34:47 I like that.

34:48 Everything about it, times, food, music.

34:51 What food did you eat?

34:52 Well, it was the same thing. It was always like grilled chicken. Yeah. Because I never wanted to go out because I wore a tie.

34:56 Yes.

34:56 I remember this. And so I never wanted to feel fat.

34:59 Yes, 100%.

35:00 Because I wasn't fat, but, you know, if you eat.

35:02 Puffy food, you're just like, whoa.

35:04 Yeah, you feel fat and then it definitely shows like in your being.

35:09 Where you're just like, yeah, I get it.

35:11 So I have Richard number three. What do you have on that one?

35:14 I mean, another one I remember where I was, there's this publishing company, Big Yellow Dog. Maren was there at the time. Me, her, and Laura were up in this upstairs room. It's weird that I, like, remember all the places. I'm realizing, as you said that a few minutes ago, I'm like, I do remember, like, places a lot. And we just had fun with that. I mean, I had had that idea. I told Maren about it at a bar, like, maybe a week or a couple of days before or something.

35:46 And she was like, yeah, let's mess with that. And so we wanted it to be fun too. Like the vibe of it. I remember that was a big thought that we had. Cause again, it's kind of actually a really sad place to be the person.

36:03 In that song, but it feels good.

36:08 It feels good.

36:08 Yeah.

36:09 You know, it feels good.

36:11 I feel kind of swaggy.

36:12 Has the pendulum swung at all to where when you would first start writing with people that you looked up to, you would go, this is crazy. I get to write with, insert whomever you admire, to where now people are doing that to you in rooms?

36:24 That can trip me out sometimes. There is a little of that. I would think starting or whatever, which also makes me be like, oh gosh, I'm not the new kid at school anyway. Because I don't know if you do this too, but I feel like I'm always... That's always the mentality too is like I haven't done anything.

36:45 It still feels– everything always still feels that way. So when someone will do that, it's kind of.

36:53 I'm like, me? Huh?

36:55 You know? And then I think about all like our heroes and that they probably feel the same way. You know?

37:01 Well, most of them.

37:02 I will find any reason to be offended to drive me, right? Like I'm always looking for that.

37:07 We're so similar.

37:08 I know.

37:08 And I was doing a podcast the other day and they were so nice. And one of them was on, they're married. One was on Love Island. One was on The Bachelor. And they were like, would you come on the podcast? I don't do a lot of podcast appearances just because I have so many shows.

37:22 Yeah, I didn't think that either. I was like, I don't know if I'm- Rarely. Yeah, that you ever do.

37:27 But I said, okay, I'll do it because they wanted to talk about my experience on Dancing with the Stars. And I kind of love talking about that show because I wasn't supposed to win the show. That's fine for me. And so I went on and they started, I was offended a little bit when they started. They were like, he's a legend in the industry. He's been, and I'm like, oh my God, guys, you're making me sound 500 years old.

37:46 Yes, that is so real.

37:48 You're like, please stop, please stop.

37:49 And they're being complimentary. To them, they're going, I'm really gassing this guy up. Like we want to build up who he is. We're showing that we respect what he, He's been podcasting since 2005.

37:59 And I'm like, oh my God, shut up.

38:02 I would freak out too. Please stop.

38:04 You're making me feel like I'm 100 years old here.

38:07 No, no, no.

38:08 I would hate that too. I found a way to be offended.

38:10 Yeah.

38:10 I mean, I would have been sweating too.

38:14 I'd be like, oh, please stop, please stop, please stop.

38:16 The one thing that really is so dumb that I get offended by this. Someone will go. You're actually funny today. It feels like I'm gassing myself up, but just bear with me. someone will go, you're so talented. And I get so, my only word is offended at that because I'm not talented. I work hard. And they're not saying it that I don't work hard. That's just a general thing you say if you like someone's work possibly. And they would go, you're so talented. And I like in my gut go, Oh, you had me all wrong. You think this is natural that I don't work hard? You think I'm not growing? And then I get.

38:49 Mad for no reason.

38:51 Yes, this is so real too.

38:51 I shouldn't get mad at that. That's still giving me a compliment.

38:54 Yeah, but real.

38:55 It was Breland who said to me, hey, they're just being nice. Like they just don't know how to express the affinity they have for you.

39:04 Yes. And that's just what you say.

39:06 And I was like, I appreciate you saying that, but I have a chip that's still directly dug into my shoulder.

39:11 Oh, yeah.

39:11 Yeah. Always.

39:12 Always.

39:12 That is a good way to say that too.

39:14 I think because I'm like you and I think I have to remember sometimes that it is what he said.

39:21 People don't know.

39:23 What to say or like how to articulate something. Not that I'm so fucking smart or something, but just meaning like. think about it I guess in the way we do you know and.

39:32 Then I got to think I've probably done that to people too and not.

39:35 Realized it yeah hundred percent.

39:37 And I've said something that they probably misconstrued or that I didn't communicate effectively yes but I will find a reason To be offended and use that as fuel. And I'm probably purposefully doing that. Subconsciously, I'm just begging for fuel to get the rocket ship going again.

39:53 100%. Because we got half the fuel. And it is just like, yeah, I do the same thing.

39:59 At number two, this is probably one of my top 25 songs in country music period.

40:07 At number two, even. I love this song so much.

40:11 Bobby.

40:12 Why haven't I? It's a dude who sings this one. Okay. It's been out a while. I wish I knew.

40:22 It came out in 2022. Great male vocalist. Tall fella.

40:31 Brett.

40:33 Love.

40:34 I miss him.

40:35 I haven't seen him in a minute. Now I'm trying to get through these songs about you. I love that song so much.

40:42 That means so much to me. I love Brett's percussion. I mean, one of the best, like another one that's like, I know I said this about Morgan earlier, but Brett, I mean, he's so up there for me vocally.

40:55 And we were in.

40:56 Such a season again, then like where we were like attached to the hip working all the time.

41:02 I love that song. I love the video.

41:04 I actually have a card from that video. Cause he kind of did in the video, the eternal sunshine of the spotless mind thing where he like goes into this place to have his like, brain erase and there's this little business card that says memory spot delete procedure that I literally used until I moved I had it on my refrigerator but I love that song I love the production everything about it that was a good time that that season of.

41:36 Life that's a good one you write really good I didn't want to say ballads. That's a ballady song, but I don't, that's not, it doesn't feel like a straight ahead ballad to me.

41:44 But yeah, you could have probably done that with it.

41:47 Like take tempo wise, if you wanted Brett, especially, I mean, he could probably make any song kind of anything, but that he wanted.

41:56 But my number one song, we are at it now. This song, the first time I heard it, there've only been three songs in this town that I have heard and went, Oh my God. Like I, whoever wrote that, I love it. Because there were big risks taken with it. One of the other ones, it was so simple and it just kept repeating itself. But the first time I heard it, I was like, this is such a giant smash.

42:20 And this was not yours, but I'm just going to compare it to another song. It was the first time I heard Meant to Be.

42:24 I was like, oh my God. I was like, that's, we talk about simple. Simple doesn't mean lazy.

42:29 No, agree.

42:30 That's the thing is it doesn't. And then that song has a crazy story. I don't speak for them, but Josh Miller, we did lives together.

42:36 He's on that.

42:37 They almost didn't write that song because I think it was like really late at night. They were out in LA and it's crazy to think for the genre, even if meant to be like didn't exist, like crazy that that almost just didn't happen.

42:53 I remember I had a Tesla at the time, and I was pushing the big buttons, flipping through, and that song came on, and it was one of those rare times where I was like, oh, I got the worm.

43:04 It's in me from that song.

43:06 100%.

43:06 This next song is like that, too.

43:08 This next song is really cool to watch perform live because of how everybody reacts to it at a certain part.

43:13 Does that give you an idea of what the song is?

43:15 Am I okay?

43:16 Yes.

43:16 Megan Maroney. Am I okay?

43:19 The little girls, it's mental.

43:21 Y'all are all Us little girls, we go crazy. Us little girls, I know, me too. Just the jumping. It is, and we kind of had no idea, I don't think. I will definitely say that. Like, no clue that that song would turn into, like, what it did. We knew it was fun, and we liked it. I remember it was a thing that Meg had that idea, and it was such, like, emo cowgirl type title that we— I was like, well, what if it was tempo though? I think no one will expect an Am I Okay by Megan Maroney to be. And she had just been dating this guy. And so it all kind of happened. We were at Luke Laird's cabin in town. And yeah, it's so crazy.

44:11 To see that.

44:12 Even on the new tour, like the Cloud Nine tour, it just goes off.

44:16 It's crazy.

44:17 It goes off.

44:18 Listen to it by yourself. That song to me, the first time I heard it, I thought such a fun song. Also a little risky to put out as a single because it just is different. It is.

44:31 But it happened to be the right different.

44:34 And that's my favorite song for that reason that you've ever written.

44:37 I am so, it is unexpected to me, but I love that it is. And now it makes sense.

44:43 That's what I said. It'd be unexpected, but it would make sense as to why.

44:47 It does make sense.

44:48 Yeah.

44:49 My 10 and one were both Maroney songs.

44:51 Which just the best.

44:54 I mean, she's so, she's definitely one of my favorite people in general. And then I think she's so important for country music and for women. And it's so, again, I say the little girls, but because they're so, but I just, I mean, I remember we were on like an amphitheater tour and the little girls like broke a barricade down.

45:19 And I was like, this is like the Beatles. Like, This is crazy.

45:22 And it was not even arenas yet, you know.

45:27 But I'm so lucky to get to work with her.

45:31 I'm going to unfairly take credit for something with Maroney.

45:34 I like Megan a lot. We had Megan in doing this stuff before she blew up.

45:38 Yes.

45:38 I was just a fan of her as a songwriter.

45:40 Agreed.

45:41 And so when she was in recently, we had just started the Netflix part of this podcast, this season of it. And I had her in and I said, you can't not play hair salon anymore. She's like, I'm not playing it anymore.

45:50 I said, you can't.

45:51 You have to play it some because like that's what my wife found.

45:55 Totally.

45:56 And put me on to her. And then the next show, I saw her play hair salon.

45:59 That's amazing.

45:59 Yeah, yeah. Now look, do I think she did it because of me? Yes.

46:03 Yes.

46:04 I would agree.

46:04 I bet she did.

46:05 Because she's like that too. She's not the one who's kind of like us. She'll log that. And it won't go anywhere.

46:13 And she doesn't play it every show, but she doesn't have to.

46:15 There just should be the thought that she might play the song that to me, to a lot of us, started it all.

46:21 Totally.

46:22 My wife found that on TikTok way, way, way back in the day and was like, you're going to love this girl.

46:27 And it was that song.

46:29 So good.

46:30 And it's so good.

46:31 Still so good. I love the artwork, all of it.

46:34 I did just vote for your song, Beautiful Things, for the CMA Song of the Year.

46:39 Thank you.

46:40 I did.

46:40 I love that song. That was a good, really good.

46:44 Connie and Jess Alexander, two of, like, definitely the most badass songwriters I know.

46:48 We got to do that with them.

46:49 And it's been really, really cool to see different fans. Like, nobody likes a freaking bully. And I just feel like there's been a lot that I've gotten to see from fans of, like, that it helped them through any kind of, like, bullying time or feeling less alone. And I think it's so important for artists, an artist like Megan to sing something like that, you know, and it's been really cool.

47:17 With, to see that, that song.

47:20 Let's take a quick pause for a message from our sponsor. And we're back on the Bobby cast.

47:35 You know who else I voted for?

47:36 Who?

47:36 CMA is going to kill me for sure.

47:38 I love it. Stir in the pot.

47:40 So there was a certain artist that I took out to open for me for a bunch of shows and I didn't really know her that well at the time. But then once I got to know her, I was like, this chick's awesome.

47:50 Yeah. A little weirdo.

47:52 Carter.

47:53 Yes.

47:53 She loves you too.

47:54 I voted for her best new artist.

47:55 That makes me so happy.

47:57 What I always found about her was- She deserves it, man. Even if she never like, pop through with mainstream commercial success, what she's starting to get, that she was going to be okay with that because she was just who she was. And she was happy with who she was. And if you didn't get it, that's your fault. That's what I felt like was coming from her. And I respected that so much.

48:15 She still liked that.

48:15 Yeah. Yeah. I was on a group text with her earlier where she was like, cool guys, nobody answered me. But anyway, I'm going to go back just because it had been a couple hours or something.

48:25 You probably saw that. It was so funny. So her, but that- To that point. She's just the best. She loves you too.

48:31 So she's your artist though. You have Gatsby records?

48:34 Yes, Gatsby.

48:35 And she's like the flagship artist and she's one of the biggest reasons I wanted to do any of it. You know, it's just like you work with so many great artists and you see them and you're like, how can I, if I can even do a small little thing that helped at all, like I want to do it because I think someone like her is that, talented and deserves it that much. And I just have never seen music feel in a more chaotic time than it does the past couple of years. So I was like very inspired when I got the opportunity to do Gatsby to do it.

49:14 You just added stress. You just added a little more stress into your life.

49:18 How much of your day is dedicated to that?

49:21 A lot.

49:22 A lot. And that's the part that's been important to me. Like I never wanted it to be something that was just, oh, she like, put her name on that to say that she did it. I mean, I was, I, right before I came here, I was on like a call, um, with MCA and her management, just walking through like the next things that we want to do.

49:46 Cause she has a lot that's about to happen.

49:48 Like Heartland, her Netflix movie, um, a really big soundtrack that's exciting separately. And then, um, just CMA week, you know, so walking through all that. And so, um, It's become a lot of my life. I think it'll be more and more as time goes on. I'm really trying to figure out how to balance it.

50:12 We need to go to dinner. I should talk to you more about it.

50:14 Yeah, you're like kids do the darndest things though because you're way too young to be running a label.

50:18 You know, it's like... Looking at you running a label.

50:21 Got to. These other people don't know what the hell they're doing most of the time. I'm just going to say that right now. So somebody's got to come in and change some things.

50:31 That was the big point to me too is I just, I don't know. I felt very called to, why not? I mean, luckily I have... through this process, like come across some really great mentors that I didn't think, you know, like Monty Lipman or Avery Lipman from Republic have become great people in my life that I look to a lot because I really respect that those are two people that kind of like me or you started trying to make a record label in a small apartment in New York City with no money.

51:07 And they have some crazy stories.

51:10 I bet Montu would never do a podcast, but he should come on here because he has great stories about just the hustle of that in the beginning. So it's been nice walking through with like those type of people to learn from.

51:23 What's up with the William Beckman kid?

51:26 Love.

51:26 He's also 31. He's not a kid, but he looks young.

51:28 Oh, yeah, he does.

51:29 He looks young.

51:30 He is like.

51:31 William and I have worked together for years, kind of like me and Cart, actually.

51:35 And he just is such an amazing singer. It's like.

51:41 He's kind of, I say Marcus King because I love Marcus too. Very different singers. But when you hang with Marcus, kind of like William, it's like they're from another time.

51:50 And it's genuine.

51:51 Like the whole thing. The personality. William's such like a gentleman. You don't really like, but it's real. And then the voice and the music. And it's got some royal or synchronic Isaac. Like all of these very cool things. And again, I just think people should know his music. I think he's that good.

52:13 How many songs do you write in a week now?

52:17 Depends. A lot less than I was, for sure. And it's also moved into this different place. I'll have to come back on. Look at me trying to get to come back on. But I've been working on a really big project with an artist that is... not country that is is well I mean there's influence I would say she's like an American poet really um but that I um never I mean she's one of my favorite artists of all time definitely one of the most talented people I've ever met and so we've been working on this project for several months um and it's turned into a lot more of that like I feel like I will work with someone on like a whole album I don't have to have every song or anything, but it feels like it's very like focused versus, you know, there was

53:12 a huge part of my career that was like every single day of the week, sometimes twice a day, I would be like just writing a song, hoping that somebody would pitch it and it would get recorded. And so I feel like it's changed. Like that I still do that, of course, but.

53:32 A lot less.

53:34 Are you familiar with the TV show Murphy Brown from back in the day?

53:36 Yes.

53:37 So there was a time when Candice Bergen was winning so many Best Actress awards that she pulled herself out of it.

53:42 Don't do that. Don't take yourself out because you're winning all the stuff. You deserve all this.

53:46 Bobby, thank you.

53:48 I need to hear that today. Don't Murphy Brown us.

53:50 I can't Murphy Brown.

53:51 No.

53:51 You're representing a lot of people.

53:52 That just reminded me of my mom, Murphy Brown. She liked that show, I think.

53:56 She did.

53:56 So did my mom.

53:57 That's how I know it too.

53:58 Yes, I think she did.

54:00 Yeah, that and Roseanne.

54:00 Yes.

54:01 That's what my mom used to watch.

54:02 Same.

54:03 You're the best.

54:04 You're the best.

54:05 Congratulations on all your success. It is so deserved.

54:08 Like, people need to see people doing stuff, and there's a lot of people that watch you and go, she's doing it at the highest level, so I can do that too.

54:16 Thanks for saying that. I hope they sleep, though.

54:20 They don't, because they won't.

54:22 If they're anything like us.

54:24 They won't. I'm so happy for you. I'm so happy we can make this happen.

54:28 Me too.

54:29 You're one of my favorite people I don't see enough, honestly.

54:31 Thanks.

54:32 I don't know how many of your favorite people you don't see often, but... If it's even three.

54:37 Yes?

54:37 Yes.

54:38 Who else would be on the list of people that you don't see that you like?

54:42 Oh, man. Well, I haven't seen Magatang lately because she's been in Europe. We usually see each other more, so I miss her. But she gets back soon.

54:50 So it's me and Moroni.

54:50 Yes.

54:51 As it should be. Good to see you.

54:54 You too, babe.

54:56 Thanks for listening to a BobbyCast production.