The Bobby Bones Show - BONUS EP: Bobby Backstage Interview with Bailey Zimmerman & Diplo

Episode Date: September 29, 2025

We recorded a bonus podcast backstage at our iHeartRadio Music Festival in Las Vegas inside the T-Mobile Arena. Bobby sat down with Diplo and Bailey Zimmerman to discuss how music unites us, their collaboration “Ashes,” how that all came together and more!See omnystudio.com/listener for privacy information.

This is an I-Heart podcast. Guaranteed human. A win is a win. A win is a win. I don't care what you're saying. Yep, that's me. Clivert Taylor the 4th. You might have seen the skits,

my basketball and college football journey, or my career in sports media. Well, now I'm bringing all of that excitement to my brand new podcast, The Clifers Show. This is a place for raw, unfills of conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated.

So let's get to it. Listen to the. the Clifford Show on the I Heart Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. The Bobby Bone Show. All right. Hey guys, Bobby here backstage, Las Vegas for our Iheart Radio 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. But watch it all. You'll be able to see it up on the socials. But we're going to go over to them now.

Bailey Zimmerman Diplo backstage before their performance at the IHeart Radio Music Festival. Hey, it's Bobby Bones backstage at the IHeart Radio Music Festival. And this whole festival is known for its once-in-a-lifetime collaborations. So how did Ashes come together, Diplo? Well, I kind of briefly met Bailey, I think at Morgan's show, one of them. And I think he's just a 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 handled it on his own on the road. Yeah. It was really cool. He literally just like randomly showed up to my house. I'm like, oh, hey, Diplo, what are you doing? He's like, I have a song. Did I want to show you? And I was like, okay.

And then now we're here playing it live. 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? 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. Do you just pull people's houses randomly and just be like, I got music? 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. Yeah. That's how you know it's Bailey's. Big trucks, big rims, flashy. Yeah, you know. to 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 boom box. Yeah. He was like, listen to this song. I played it. John Cusack. Right in the parking lot.

He was like, that's it. Bailey, I'll go to you on this one. All right. Who would you want to see duet together if you could? You can magically match two people, one dead, one alive. Let's do it like that. Okay, all right, all right. Hmm.

Or you can pick a dead person with you, but it has to be dead person. I'm going to go. Okay, all right, deal. Yeah, it's got to be a dead person only. All right. If I could make a song with anybody that isn't alive right now, I'd probably have to. You can't pick Jesus. That's the cop-out answer.

Okay, everybody wants to make a song with Jesus. Okay. Got it, got it, got it. Honestly, probably, probably Chester, Bennington. Lincoln Park. Yeah, Lincoln Park. Yeah. Yeah, big fan.

Either that or Kirk, Cobain. That is good. That would be all so crazy. Same vibe. Diplo are you? Shoot, I don't know it's going to be next. Well, there's nobody else. Damn, okay.

Well, who would you do with Bobby? No Jesus. No, I was going to go back to Jesus. I'm talking about a mixtape with Jesus, but then. Okay, if I were going to, Andy Kaufman. Oh, like a spoken word album? Yeah, like funny spoken word. Kurt's a good one.

I think David Bowie, for me. He was such a legend. kind of every genre and did whatever he wanted. Dipla, I'll go to you on this one. When you record music, do you go in knowing you want to make a song that sparked a certain emotion or at times, do you have a song and you feel, but then you find because you're recording it, it sparks a different kind of emotion, so you alter that? 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 on it 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? What about you, Bailey? Is there ever a song that you write and it feels it's an uptempo or a ballad and you switch it? Like you change it and you go, what if we shift this because it feels different? I feel like that's always later in the process. Like I'll write it like the same thing. Just Blake, blank slate, acoustic guitar. And then you start just writing off of like immediate emotion. Like what are those, what does that track or chords make you feel? And then it's usually my producer, Austin. That'll be like, we should change this because this will feel a little better here and there. And we should.

this tempo here and do this. So yeah, it usually comes later for me. When do you feel driven to listen to music? Like when you're just listening for listening's sake, like what's the time when you turn it on, just listen to old, old stuff that makes you feel good? 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. What's your comfort music, Bailey? There's this, okay, I'm not even gonna 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. How did you come across that to begin with? Like what about your algorithm? Well, 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 going to 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, this is nice. Riding around Nashville. Massaging yourself, like rubbing your own shoulder as you drive?

Yeah. Either that or I've been on I've been on Cizza's like 2014 album So yeah I guess that too Speaking of massages was my dad's birthday yesterday And I got him at masseuse to come to his house

Near Daytona I know a great playlist to play Yeah I didn't If I knew Yeah yeah yeah yeah yeah But he had never really got a massage before Either really? Yeah that's cool

What did he say about his first massage Did he hit you up after? I got to hit him up was yesterday So I'm gonna have to remind him In the playlist we can have for next time Yeah. 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. I would say 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. Yeah. 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 they come together as one. Do you see that from up on stage? Every festival is different because I'm a DJ.

I kind of look at the crowd and be like, what's going to work? What's going to, 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 as to, you can always play like great set, but if you really make people go like, like, I didn't know I liked that. You know, 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 in places where like the music's contraband, you know, and you play records with them. They're 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. I appreciate the time. guys congratulations on the new song. Looking forward to seeing a live performance tonight.

Good luck, guys. Have good show. Thank you. Thanks, dude. A win is a win. A win is a win. I don't care what you're saying. Yep, that's me, Clifford Taylor the 4th.

You might have seen the skits, the reactions, my journey from basketball to college football, or my career in sports media. Well, somewhere along the way, this platform became bigger than I ever imagined. And now I'm bringing all of that excitement to my brand new podcast, The Clifford Show. This is a place for raw, unfiltered conversations with some of your favorite athletes, creators, and voices that not only deserve to be heard, but celebrated. One week, I'll take you behind the scenes of the biggest moments in sports and entertainment, and the next we'll talk about life, mental health, purpose, and even music. The Cliverts Show isn't just a podcast, it's a space for honest conversations, stories that don't always get told, and for people who are chasing something bigger. So, if you've ever supported me, or you're just chasing down a dream, this is right where you need.

to be. Listen to the Clifford show on the IHeart Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok. There's two golden rules that any man should live by. Rule one, never mess with a country girl. You play stupid games, you get stupid prizes. And rule two, never mess with her friends either. We always say that trust your girlfriends. I'm Anna Sinfield. And in this new season of The Girlfriends, Oh my God, this is the same man. A group of women discover they've all dated the same prolific con artist.

I felt like I got hit by a truck. I thought, how could this happen to me? The cops didn't seem to care. So they take matters into their own hands. I said, oh, hell no. I vowed. I will be his last target. He's going to get what he deserves. Listen to the Girlfriends.

Trust me, babe. On the IHart Radio app, Apple Podcasts, all. wherever you get your podcast. Everyone, I'm Ago Wodam. My next guest, you know from Step Brothers Anchorman, Saturday Night Live, and the Big Money Players Network. It's Will Ferrell. Woo, woo, woo, woo.

My dad gave me the best advice ever. I went and had lunch with them one day, and I was like, and Dad, I think I want to really give this a shot. I don't know what that means, but I just know the groundlings. I'm working my way up through, and I know it's a place they come. Look for up-and-coming talent. He said, if it was based solely on talent, I wouldn't worry about you, which is really sweet. Yeah.

He goes, but there's so much luck involved. And he's like, just give it a shot. He goes, but if you ever reach a point where you're banging your head against the wall and it doesn't feel fun anymore, it's okay to quit. If you saw it written down, it would not be an inspiration. It would not be on a calendar of, you know, the cat, just hang in there. Yeah, it would not be. Right, it wouldn't be that. There's a lot in luck.

Listen to Thanks, Dad, on the IHeartRadio app, Apple Podcasts, or wherever you get your podcast. This week on the Sports Slice podcast, it's all about the NFL draft, and we've got a special guest. The director of the NFL's East West Shrine Bowl, Eric Galco, joins the Sports Slice podcast to break down what really matters when evaluating draft prospects. From hidden traits teams look for to the biggest mistakes franchises make to the players flying underline. under the radar. This is the insight you won't hear anywhere else. If you want to understand the draft like an insider, you don't want to miss this episode.

Listen to the Sports Slice podcast on the Iheart radio app, Apple Podcasts, or wherever you get your podcast. And for more, follow Timbo Slica Life 12 and TikTok podcast network on TikTok. In 2023, former bachelor star Clayton Eckerd found himself at the center of a paternity scandal. The family court hearings that followed

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This isn't over until justice is served in Arizona. Listen to Love Trapped podcast on the IHeart Radio app, Apple Podcasts, or wherever you get your podcasts. Bobby Blonde. 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. E had hired me to come out and be on the red carpet for a TV show. And there's a clip of, I asked 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. It was a joke question. And then I think he did that. But a 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 three 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 wouldn't know what a manager does. He didn't know about fees. He didn't 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 and 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 a know him a little bit too, it's the Morgan Wall and 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 them 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.

and 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 Exa 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 story is super, just professionally.

Like, he was, like, with 36 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. When I first moved to town, I lived 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 gate. community and it was kind of crazy because like rascal flats late singer lived there carry lived there uh 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'd play 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 it 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 Jellyroll's been that guy, and he was here today, he's lost 200 pounds, which is crazy to see. He's like almost half 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

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 see him here tonight And I hadn't seen him 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 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 is 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 L.O. 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 them. But saw Brian Adam. It's pretty crazy to see somebody you've only seen on television. Saul Maroon 5, dude, Adam Duritz. No, Adam Levine.

Yeah, Duritz 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 is playing tonight. And he said, Tate McCray. And I said, what 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 one. 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 mic earlier. I'll give you one of the behind-the-scenes thing. We were doing this video shoot with Bailey and Diplo. And I was miced 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're doing the Santa Fe, the Palisade Hybrid, which is awesome. So check it out. Check out Hyundai, if you haven't, like the elite cars.

And they sponsored the house of music in front of the arena, which is 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 IHartRadio Music Festival, 2025, fantastic. I'm watching the screen now. I think I saw my uncle. Nope, it's Sammy Hagar.

It's Sammy on the stage right now. And Uncle Sammy is going hard right now. Looks like they just pulled him out of the... Hey, won'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 this 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 IHart Radio 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.

A win is a win. A win is a win. I don't care what I'm saying. Yep, that's me. Clifford Taylor the 4th. You might have seen the skits, my basketball and college football journey, or my career in sports media.

Well, now I'm bringing all of that excitement to my brand new podcast, the Clifford Show. This is a place for raw, unfilled conversations with athletes, creators, and voices that not only deserve to be heard, but celebrated. So let's get to it. Listen to the Clifford show on the IHeard Radio app, Apple Podcasts, or wherever you get your podcast. And for more behind the scenes, follow at Clifford and at TikTok Podcast Network on TikTok.