The Bobby Bones Show
BONUS EP: Bobby Backstage Interview with Bailey Zimmerman & Diplo
September 29, 2025
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.
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.
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])
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])
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.
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])
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])
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
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.
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.
For more festival highlights and to catch the live performances, tune into the replay on Hulu or follow The Bobby Bones Show social channels.