BONUS EP: Bobby Backstage Interview with Bailey Zimmerman & Diplo

Summary

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The Bobby Bones Show

BONUS EP: Bobby Backstage Interview with Bailey Zimmerman & Diplo
September 29, 2025

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Episode Overview

In this special backstage episode recorded at the iHeartRadio Music Festival in Las Vegas, host Bobby Bones sits down with country breakout Bailey Zimmerman and genre-hopping super-producer Diplo. The conversation, sparked by their collaboration "Ashes," dives into how the unlikely pairing came about, the creative process, their musical inspirations, and standout fan moments. The exchange is informal and energetic, peppered with candid industry insights, banter, and personal reflections on pressure, connection, and unexpected musical comforts.

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Key Discussion Points and Insights

1. The Origin of "Ashes": Musical Serendipity

[01:02 - 02:48]

• How Bailey & Diplo First Connected:
  • Diplo describes meeting Bailey at a Morgan Wallen show, being impressed, and seeking Bailey out in Nashville with a new "sound" in mind.
  • Diplo: “I think he's just the guy in Nashville. He's cool as hell. And I had a new kind of sound I wanted to do, and I think he's the one guy that could carry it.” ([01:24])
• First Studio Session:
  • Diplo showed up at Bailey's house on a whim before Bailey left on tour.
  • Bailey: “He really just, like, randomly showed up to my house, and I’m like, oh, hey, Diplo, what are you doing?...Now we're here playing it live.” ([01:48])
• Bobby Bones laughs about the image of Diplo showing up, boombox in hand:
  • Bailey: “Imagine that...you walk outside of your house and Diplo is just standing in your driveway...like, listen to this song.” ([02:26])
• On the recording process:
  • The initial home demo was reworked for the release.
  • Diplo: “We changed the key a little bit, changed the tempo kind of like out of how he liked it, and then he made it his own.” ([02:05])
  • Diplo often pulls up to people's houses with music ideas—sometimes they open the door, sometimes not.

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2. Dream Musical Collaborations (Alive or Dead)

[02:48 - 03:54]

• Bailey’s picks:
  • Bailey: “Honestly? Probably Chester Bennington...Either that or Kurt Cobain. That would be also crazy.” ([03:21]–[03:28])
• Bobby jokes about not choosing Jesus; Diplo muses about Bowie:
  • Diplo: “I think David Bowie, for me, he was just a legend and did kind of every genre and did whatever he wanted.” ([03:54])
• Bobby goes meta:
  • Bobby Bones: “If I were going to...Andy Kaufman...like a spoken word album?...like funny spoken word.” ([03:50])

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3. Creative Approach: Genre, Emotion & Spontaneity

[04:01 - 04:38]

• On musical intention:
  • Diplo: “I just go with the blankest slate you can imagine. Like, I don't have any idea what I'm doing...what is the weirdest thing I can make and how can I make it make sense? And then the emotions come later.” ([04:13])
• For Bailey, shaping a song’s feel often happens in later production:
  • Bailey: “I'll write it...blank slate acoustic guitar. And then you start just writing off of, like, immediate emotion...usually my producer, Austin, [says]...we should up this tempo here and do this. So, yeah. Usually comes later…” ([04:38])

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4. Comfort Music & Playlists: Massage Music, Anyone?

[05:02 - 06:46]

• When and how do they listen to music for pleasure?
  • Diplo: “My car, man...the best sound system...I like to listen to new music, too, but, like, the classics...Fleetwood Mac...” ([05:12])
• Bailey reveals his secret playlist:
  • Bailey: “I found this awesome playlist, and it's called Massage Music that's Not Boring. And it actually makes me so Zen when I'm trying to chill...” ([05:29])
  • The playlist discovery came from his first-ever massage experience while touring.
  • Bailey: “I was like, massage music. That's not boring. And then it just came up. And from then on, I just find myself going back to that playlist.” ([05:53])
• Diplo shares he arranged a first massage for his dad’s birthday, connecting over new experiences.

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5. The Power of Music to Connect Fans

[06:54 - 08:22]

• Bailey’s perspective:
  • Bailey: “Every show of mine… reminds me why I do music… just the stories that come from how far this music has reached…they’ve connected with me somehow through music…it’s crazy.” ([07:03])
• Diplo on festival crowds:
  • Diplo: “Every festival is different. Cause I'm a DJ...what's gonna, like, change their attitude or make them feel something they never felt before?...when you play records for [audiences in places like Pakistan]...the world is so united, you know, we don't know it, but music is the one thing that everybody shares in common.” ([07:46])

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Notable Quotes & Memorable Moments

• Bobby Bones: “Imagine that...you walk outside of your house and Diplo is just standing in your driveway…with a boombox...listen to this song.” ([02:26])
• Diplo: “I do that actually a lot. It works. Sometimes they don't answer the door...” ([02:14])
• Bailey Zimmerman: “Probably Chester Bennington...Either that or Kurt Cobain.” ([03:21]–[03:28])
• Diplo: “I think David Bowie, for me, he was just a legend and did kind of every genre and did whatever he wanted.” ([03:54])
• Bailey: “I found this awesome playlist, and it's called Massage Music that's Not Boring. And it actually makes me so Zen...” ([05:29])

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Important Timestamps

• 01:02 – Start of interview, intro to Diplo & Bailey Zimmerman
• 01:23 – 01:59 – Story behind the making of “Ashes”
• 02:50 – 03:54 – Dream collaborations (dead/alive artists)
• 04:01 – 04:38 – Approach to creative process/emotion in music
• 05:02 – 06:19 – Comfort music & “massage music” playlist story
• 06:54 – 08:22 – Music’s power to connect people globally

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Host’s Post-Interview Reflection

[09:23 – 18:57]

• Bobby Bones offers personal anecdotes about his early encounters with Diplo and Bailey Zimmerman, highlighting Bailey’s unorthodox rise in the music industry from pipeline worker to sudden viral success during the pandemic.
  • Bobby Bones: “Bailey was basically working for a pipeline and really didn’t sing much...I did the first ever interview he ever did. He came over to my house because I thought his story was so wild…” ([10:24])
• Stories of mentorship and advice for Bailey as fame accelerated, drawing parallels to Bobby’s own background.
• Bobby reflects on country/hip-hop star Jelly Roll’s transformation, hard-won success, and continued authenticity and generosity.
• Fun behind-the-scenes moment about singing the praises of the Hyundai Santa Fe (the festival vehicle sponsor) to Bailey—without realizing he was still wearing a live mic.
• Additional festival color: brief encounters with LL Cool J, Bryan Adams, Maroon 5, and Sammy Hagar.

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Summary

This episode offers a lively, behind-the-scenes look at creative partnership, the unpredictable paths of collaboration, and the ways music forms unlikely connections across genres—and across the globe. Bailey Zimmerman and Diplo’s different but compatible processes highlight the possibilities of spontaneous, boundary-pushing creativity. With Bobby Bones’ personal, supportive tone, listeners are treated to both a crowd’s-eye and artist’s-eye view of the festival experience and music’s unifying power.

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For more festival highlights and to catch the live performances, tune into the replay on Hulu or follow The Bobby Bones Show social channels.

Transcript

[A]

This is an iHeart podcast.

[B]

Question. What's the best and worst way to communicate with friends? Obviously, it's messaging. Messaging is great, but it can also go off the rails when I speak on a group chat. I want it to be easy without any issues. WhatsApp can help. You can message privately with everyone, and you can edit messages, create polls, do pinned messages, and send invites. Plus you can send photos and videos, and they look better. It's time for WhatsApp. Message privately with everyone.

[A]

All right. Hey, guys, Bobby here backstage Las Vegas for our iHeartRadio music festival. And we're about to talk with Bailey Zimmerman and diplo, and it is with Hyundai. And I hope you get a chance to go over and watch the video. We just shot a really fun video where it's basically, I'm supposed to drive them around the city, but then I'm really early, and they're also kind of late. And then we get in the Hyundai.

[B]

But watch it all.

[A]

You'll be able to see it up on the socials. But we're gonna go over to them now. Bailey Zimmerman, Diplo backstage before their performance at the iHeartradio Music Festival. Bobby Bones. Hey, it's Bobby Bones backstage at the iHeartradio Music Festival. And this whole festival is known for its once in a lifetime collaborations. So how did Ashes come together? Diploma.

[C]

Well, I kind of briefly met Bailey, I think, at Morgan's show, one of them. And I think he's just the guy in Nashville. He's cool as hell. And I had a new kind of sound I wanted to do, and I think he's the one guy that could carry it. And I came to his house. I had a show. I pulled up real quick. He was about to leave on tour. You're about to jump in your tour bus. And we had like three hours play the record for him. We kind of, like got a scratch, and then he handed on his own on the road.

[D]

Yeah, it was really cool. He really just, like, randomly showed up to my house, and I'm like, oh, hey, Diplo, what are you doing? He's like, I have a song that I want to show you. And I was like, okay. And then now we're here playing it live.

[A]

And so you record, you say like a scratch, like the first version at the house. Did you use any of that in the actual track?

[C]

No, we changed the key a little bit, changed the tempo kind of like out of how he liked it, and then he made it his own.

[A]

Do you just pull up people's houses randomly Just be like, I got music.

[C]

I do that actually a lot. It works. Sometimes they don't answer the door, but he had a big ass truck in his yard. I knew it was his house.

[A]

So, yeah, that's how you know it's Bailey's. Big trucks, Big rims. Flashy.

[D]

Yeah. You know, it's me, honestly, seeing Diplo just like park and get out and be like, hey. Is like, dude, imagine that. Like you're listening right now. You walk outside of your house and Diplo is just standing in your driveway and he has. Basically, you just was there with a boombox. He was like, listen to this song.

[C]

I played it. He was like, that's. That's it.

[A]

Bailey, I'll go to you on this one.

[D]

All right.

[A]

Who would you want to see duet together if you could just. You can magically match two people, one dead, one alive? Let's do it like that.

[D]

Okay. All right, all right.

[A]

Or you can pick a dead person with you, but it has to be dead person.

[D]

I'm gonna go, okay, all right.

[A]

Yeah, it's gotta be a dead person only.

[D]

All right. If I. If I. If I could make a song with anybody that isn't alive right now, I'd.

[A]

Probably can't pick Jesus. That's the cop out answer. Okay. If anybody wants to make a song with Jesus. Got it. Got it.

[D]

Honestly? Probably. Probably Chester Bennington.

[A]

Lincoln Park.

[D]

Yeah, Lincoln Park.

[A]

Yeah.

[D]

Yeah. Big fan. Either that or Kurt Cobain. That would be also crazy.

[A]

Same vibe. Diplo. Yeah.

[C]

Yeah, Shoot. I didn't know what's going to be next.

[A]

Well, there's nobody else.

[D]

Damn.

[C]

Okay, well, who would you do with Bobby? No.

[A]

Jesus. No, I was going to go back.

[C]

To Jesus mixtape with Jesus.

[A]

Okay. If I were going to Andy Kaufman.

[C]

Oh, like a. Like a spoken word album?

[A]

Yeah, like funny spoken word.

[C]

Kurt's a good one, I think. I think David Bowie, for me, he was just a legend and did kind of every genre and did whatever he wanted.

[A]

Diplo, I'll go to you on this one. When you record music, do you go in knowing you want to make a song that sparks a certain emotion? Or at times do you have a song you feel, but then you find because you're recording it, it sparks a different kind of emotion, so you alter that.

[C]

I just go with the blankest slate you can imagine. Like, I don't have any idea what I'm doing. Like, it could be like a reggae record, country record, metal. I just kind of go in, like, what is the weirdest thing I can make and how can I make it make sense? You know? And then the motions comes later. That's when the songwriting comes and everything kind of fits in, you know?

[A]

What about you, Bailey? Is there ever a song that you write and it feels it's a up tempo or a ballad and you switch it, like, you change it and you go, what if we shift this because it feel different?

[D]

I feel like that's always later in the process. Like, I'll write it like the same thing, just blank. Blank slate acoustic guitar. And then you start just writing off of, like, immediate emotion. Like, what are those? What does that tracker chords make you feel? And then it's usually my producer, Austin, that'll be like, dude, we should change this, because this will feel a little better here and there, and we should up this tempo here and do this. So, yeah. Usually comes later for me. Yeah.

[A]

When do you feel driven to listen to music? Like, when you're just listening for listening sake. Like, what's the time when you turn it on just to listen to old, old stuff that makes you feel good?

[C]

My car, man. Like, just kind of like driving. It's the best sound system. You just kind of like, roll. And then I like to listen to new music, too, but, like, the classics, you know, put on, like, Fleetwood Mac or something. But I always like to listen to something I never heard to kind of like, hear what's going on, you know?

[A]

What's your comfort music, Bailey?

[D]

There's this. Okay, I'm not even going to lie. I might get grilled for this, but I go, I found this awesome playlist, and it's called Massage Music that's Not Boring. And it actually makes me so Zen when I'm trying to chill and trying to just, like. Just, like, feel myself, you know? So I listen to that.

[A]

How did you come across that to begin with? Like, what about your algorithm?

[D]

Let's get into this. So we talk about never having things in life, and one of the things I had never experienced was a massage. And I'd been torn so much, and I'm like, you know what? I'm gonna get a massage. I think. So when I was looking for music to put on, I was like, well, I don't want to be boring. So I was like, massage music. That's not boring. And then it just came up. And then from then on, I just find myself going back to that playlist. Like, just riding around. This is nice.

[C]

Riding around Nashville.

[A]

Massaging yourself, like, rubbing your own shoulder as you drive.

[D]

Yeah. Either that or I've been on. I've been on SZA's like, 2014 album, so. Yeah, I guess that too.

[C]

Speaking of massages, it was my dad's birthday yesterday, and I got a masseuse to come to his house near Daytona.

[A]

I know a great playlist to play while he.

[C]

If I knew. But he had never really got a massage before either.

[A]

Really?

[C]

Yeah.

[A]

Yeah.

[B]

That's nice, what he said.

[A]

What did he say about his first massage? Did he hit you up after?

[C]

I gotta hit him up. It was yesterday, so I'm gonna have to remind him. It's in the playlist, so we can have it for next time.

[D]

Yeah.

[A]

Final question. Do you have a cool memory that stands out for how music has connected fans together, or an event you've been at where you've seen fans really come together? And. Bailey, I'll go to you first.

[D]

I would say every. Every show of mine is like. It reminds me why I do music. And hearing. We were talking about earlier today, just the stories that come from, how far this music has reached in the world and just, like, what it's got them through and why they're at the show and hearing those stories. Oh, yeah, it's like. Yeah, it's like connection on a whole different level. You're like, I know this person and they know me, and they feel like all the way across the world, they've connected with me somehow through music. It's crazy.

[C]

Yeah.

[A]

What about you? What about when you play a festival? And it's like, people that are there for kind of everybody and nobody at the same time, but. But they come together as one. Do you see that from up on stage?

[C]

Every festival is different. Cause I'm a dj. I get to kind of look at the crowd and be like, what's gonna work? What's gonna, like, change their attitude or make them feel something they never felt before? So I always try to think of that. It's like a DJ's job is to. You can always play, like, great set, but if you really make people go, like, I didn't know I'd like that. That feels like a real skill set that I love to do. But I travel all over the world, so going places like Pakistan, you know, like, my first time, I was like, people party here. And then I was like, they do the songs from YouTube and places where the music's contraband. You know, when you play records for them, they like. It's just like, the world is so united, you know, we don't know it, but music is the one thing that everybody shares in common.

[A]

I appreciate the time, guys. Congratulations on the new song. Looking forward to seeing a live performance tonight. Good luck, guys. Have a good show. Thank you.

[D]

Thanks, dude.

[B]

I'm going to assume that everybody messages their friends. I'm also going to assume that sometimes you run into issues when messaging, especially during group chats. It is really important that my digital messaging is clear. No mistakes. It's also important when I send messages that they send quickly and that I get responses quickly. WhatsApp can help with all that. First, you can message privately with everyone in a group, even if you're using totally different phones. Sent a message too fast and you regret it?

[A]

No problem.

[B]

Just edit it. And when the chat gets a little too intense, you can switch to a.

[A]

Group video call and actually talk it out.

[B]

Photos and videos come through. Clear messages get delivered without gaps or delays. Plus, WhatsApp has so many great features like polls, pinned messages, even event invites with RSVPs.

[A]

So planning stuff just doesn't turn into.

[B]

A big old mess. It just makes a lot of sense. It's time for WhatsApp message privately with everyone.

[A]

Bobby Blooms. All right. Awesome to hear from those guys. My first time ever meeting Diplo and he doesn't remember, and he shouldn't remember because I'm sure they meet like 10,000 people. I was doing the red carpet for the Grammys for E. He had hired me to come out and be on the red carpet for a TV show.

[B]

And there's a clip of I asked.

[A]

Diplo the question, does he ever hear sounds, like random sounds, like when you open the door at the gas station and it goes ding dong. Like, has he ever made a song after something like that? And I think he made a song after with that idea. That's all I'm saying. I think I inspired that idea because I'd never heard the idea and it was a joke question and then I think he did that. But really cool guy. And obviously Bailey. Super cool. Crazy to see someone like Bailey or even Jelly Roll explode in the past couple of years. I mean, the thing about Bailey that's so interesting, if you don't know Bailey's story, and sometimes it's hard to know the story that come up once they get so big. But Bailey was basically working for a pipeline and really didn't sing much. Like he sang at home and had sang one time and had put it on social media. And I did the first ever interview he ever did. Like, he came over to my house because I thought his story was so wild because he wasn't like, on the radio or anything. He had this crazy streaming success and I was so interested in it. And the first interview he ever did, he came and he sat for an hour with me and he said that he went to bed, put one video up, it had like 3 million views. The next day he called his job and he quit working on the pipeline. And this is all during COVID as well. He didn't know what a manager was. And you really wouldn't, unless you've been in this industry. Like, you really. You wouldn't know what a manager does. He didn't know about fees, you know, the difference in managers and agents. And he had to learn all of that kind of himself because he was driving down. He was from the Midwest and he would drive down all the time every week during COVID and take these meetings. And he talks about how he had a meeting with an agent once in a record label, and he didn't know the difference. He had no idea what they were trying to get him to do. But he signed a deal. Obviously, he's massive now. And, you know, for him, just talking with him a lot and getting to know him a little bit too. It's the Morgan Wallen tour. When Morgan called him to ask him to open, I know that was super significant in his life. Bailey's also a kid, and I say kid because he's quite a bit younger than I am. But when he started to make it, we grew up very similarly. Like, I never had a bedroom growing up. Grew up very poor. Same thing with Bailey. And Bailey was one of those kids. I was like, hey, dude, here are the things you don't want. And I kind of walked him through the things you can get in trouble doing and not be canceled, and the things that you can't do because you will get canceled. And I was like, if you ever have to go to jail, you can call me at any time. And thank God he's never had to go to jail. We appreciate that about Bailey, but he's a great, great kid.

[B]

And he's.

[A]

It's crazy to see how fast he's blown up and like in the country music critical mass, but even outside of country music, because again, with Big X, A Plug, and with Diplo, and I think both are tonight, which is pretty crazy. Was with Jelly Roll earlier at the festival. And that's another guy that's been pretty amazing to see, like, Jelly Roll stories. Super. Just professionally. Like, he was like with three six Mafia back in the day. Like, he was a hip hop artist. Like a full hip hop Artist and I would see Jelly Roll on the golf course in Nashville. I, when I first moved to town, I lived on, in this gated community. I never lived in a gated community, but I was starting to make money and I had been like jumped. I'd been attacked. I got pistol whipped at an ATM once. I got jumped at work, outside of work, going in. And so when I moved to Nashville, they made me move somewhere that either had security or had gates. It was kind of part of the deal. And so I moved into this gated community. It was kind of crazy because like Rascal Flats lead singer lived there, Carrie lived there, I moved there and there's a golf course and I would see Jelly Roll on the golf course. Except I didn't know him from anything other than people would say he's a very face tatted rapper. But he was also on the golf course and he was in a country club. And I thought the juxtaposition of that was crazy. So that's how I knew Jelly Roll to begin with. He played golf with like Steve Hodges who was like a record guy. And so I would see Jelly Roll and wouldn't know much about him until later he got into the country music space. Now he was a fan of our show and we were probably his first ever country interview that he did. And he came in for like 45, 50 minutes. That interview has been streamed millions of times at this point. But even then you could tell the guy was super appreciative for all the new things that had happened to him. Now he's got a really great come up story as well. Like spent a lot of time in prison, like cut a lot of his creative teeth in prison and now goes back to prisons a lot and works with inmates and has built recording studios in prisons just so these guys and women know that there's, when you do get out, like there is a way to actually be successful. But Jelly Roll's been that guy and he was here today. He's lost 200 pounds, which is crazy to see. He's like almost half, you know, of what he used to be. He had a wrestling shirt on which is, you know, there's nothing more Jelly Roll than Jelly Roll wearing a wrestling shirt. Another thing about Jelly that was super cool is what he, he was a wrestler, like Raw and he wrestled Logan Paul and like for a guy that came up growing up in the south that loved wrestling, actually got to go and wrestle like on a pay per view, like it's super cool. And to be able to, to see him here tonight, and I hadn't seen him in probably, like, three months. But the cool thing about Jelly Roll is that he remembers everybody's name. And if you were like, I don't want to use the word loyal, because I wouldn't say I was loyal. But he was a fan of the show. His mom was a fan of my show. And as soon as he sees you, it's like, what a big hug. In this situation, too, I would expect you kind of know what you're walking into with interviews, but I saw Jelly Roll the last time before this, I was in New Orleans for the super bowl, and. And I was on Fox, and I was doing. I was giving away an award for the NFL honors, and Jelly Roll was a part of one of the sketches. And again, there are much more, much cooler people there than me at this event. But Jelly Roll's in the second row, and as soon as the lights go down and they go off of the television to commercial, first person yelling Bobby from the crowd was Jelly Roll. So that's just one of those guys that as soon as you see him and he's so nice and kind, you're like, is that real? For sure is real. We were walking in, we saw LL Cool J. He's a big dude. Like, still a big dude. Full, long leather, like, still puts on a super energetic, like, sweaty show. But that was super cool. Brian Adams. Rumor is he had everybody clear the room earlier when he was going into the room, and I thought, well, that's interesting. Brian Adams, because that's, like, got my first real. And, you know, some people don't want people, like, staring at him. I get it. But then when I saw him walk by, he had, like, one person with them. Usually it's people that have, like, 20 people inside their entourage. So I don't really know if that story is even true that he didn't want people looking at him, but saw Bryan Adams. Pretty crazy to see somebody you've only seen on television. Saw Maroon 5, dude. Adam Duritz. No, Adam. Adam Levine. Yeah. Duras is kind of gross. Thank you. Full of tattoos. I was talking to a guy a few minutes ago, and I was like, hey, who do you want to see? And this guy's probably, like, 65 or so. And I thought maybe he'd say Sammy Hagar, because Sammy Hagar's playing tonight. And he said, Tate McRae. And I said, well, how about that? Look at you. Look at you. He's like, I bet she's a great performer. I was like, I bet that's my. So it's an interesting night tonight. This is always the coolest festival. Big thanks to Hyundai as well, because one they give me a car and it's my favorite car. It's awesome. And I was caught on Mike earlier. I'll give you one other behind the scenes thing. We were doing this video shoot with Bailey and Diplo and I was miked like an hour before. So I had this mic on the whole time. And the Hyundai people have headphones because they want to hear the shoot. I forget that I'm wearing a mic because you don't see the mic. It's taped to my chest. And Bailey comes up and he's like, do you like this car? And I'm like, dude, if I didn't have this car given to me, I would buy the car. And he was like, are you serious? I said, I made my brother in law buy this car. And so it's a fantastic car. Like I have right now, I have the Santa Fe, but we were doing the Santa Fe, the Palisade hybrid, which is awesome. So check it out. Check out Hyundai if. If you haven't like the elite cars. And they sponsored the in the house of music in front of the arena, which was super cool. So that's what we got from here. Thank you guys for listening to this. Again, thanks to Diplo and Bailey Zimmerman, all of our guests at iHeartRadio Music Festival 2025. Fantastic. I'm watching the screen now. I think I saw my uncle. Nope, it's Sammy Hagar. It's Sammy Hagar on the stage right now. And Uncle Sammy is going hard right now. Looks like they just pulled him out of the. Hey, why don't you get up there and do a couple songs? And he's doing them. So super cool. Thank you guys for listening. And by the way, you can watch the show. I know they're going to do a replay on Hulu. We'll give you more details on the show. But if you want to watch the iHeartRadio music festival, we'll give you all those as well. All right, you guys have a good day. See you later. No need to clap.

[B]

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[A]

This is an iHeart podcast.