The Bobbycast #536: Matthew Ramsey (Old Dominion)

Podcast: The Bobby Bones Show
Host: Bobby Bones
Guest: Matthew Ramsey, lead singer of Old Dominion
Date: September 12, 2025

Episode Overview

Bobby Bones sits down for an in-depth conversation with Matthew Ramsey, frontman of the country band Old Dominion, to discuss the band’s origin story, the dynamics behind the scenes, mental health, missed opportunities (including turning down gigs with Taylor Swift), creative journeys, memorable industry moments, and the experience of building a career at a later stage than most. The episode offers candid insight into leadership, vulnerability, the pressures of creative success, and what it really means to chase joy instead of just accolades in music—and life.

Key Discussion Points & Insights

1. Old Dominion’s Band Dynamics & Member Participation

[05:06-07:15]

• Bandmate Wit’s absence in band photos:
  • Matthew Ramsey shares: Wit suffers from “crippling social anxiety,” so the band reached a new agreement to allow him to skip interviews and promo events but still fully participate in musical aspects.

    “Anything that involves playing music, he’s there… but other than that, he’s on his own, which he appreciates.” —Matthew Ramsey (06:00)

  • Open discussion on accommodating individual needs in a team, and how mental health is increasingly recognized in band decisions.
  • Ramsey emphasizes, “Every personality needs to be led differently.” (07:24)

2. Creative Leadership, Individual Experiences, and Growth

[07:52-08:41]

• Acceptance that members experience the same performance differently and that’s okay.
• Ramsey reflects on learning “two things can be true at once” from his marriage, and how he applies it to band leadership.

3. Matthew’s Artistic Journey: Art Before Music & Early Jobs

[09:49-11:38]

• Ramsey studied illustration at Virginia Commonwealth University, initially pursuing art as a career.
• Worked at a stained glass factory, painting and designing church windows—an early pursuit blending art and craft.

4. Cravings for Normalcy vs. the Drive of Creativity

[11:42-13:48]

• Both Bones and Ramsey discuss the tension between wanting a “normal” life and the relentless drive to create and prove oneself.
• Notable quote:

  “I wish I was the type of person that was cool with [normalcy].” —Matthew Ramsey (11:53)

• The pair agree that personal ambition is a double-edged sword—never fully satisfied, but propelling them forward.

5. The Story Behind ‘Barbara’ and Album Naming

[13:48-16:28]

• “Barbara” as an album title started as a joke, not connected to a song or a real Barbara.
• The character “Barbara” developed spontaneously; the cover model was in her first modeling job.

  “Then this character just appeared in all of our brains.” —Matthew Ramsey (15:12)

6. Turning Down Taylor Swift – Twice

[01:41, 16:31-17:47]

• Ramsey was twice offered a spot as acoustic guitarist and background vocalist for early-career Taylor Swift, turning it down both times—first for the birth of his child, second to focus on writing.

  “I was super broke and needed the money, but ultimately decided that’s not why I moved here.” —Matthew Ramsey (01:41, 17:40)

7. Songwriting & Nashville Wisdom

[20:59-24:35]

• Matthew only moved to Nashville to be a songwriter, studiously avoiding the stardom chase.
• Shares formative advice from songwriter Darrell Scott:

  “If you’re moving there to be a star, then don’t do it. But if you’re moving there to surround yourself with the best songwriters… then by all means, you should go.” —Darrell Scott via Ramsey (21:30)

• Ramsey passes on that ethos: authenticity matters more than trend-chasing.

8. Old Dominion’s Formation & First Big Gamble

[26:59-29:16]

• Band was a loose collaboration at first—friends playing out for fun and showcasing songs.
• “Break Up with Him” was the first song they wrote together and chose to hold back from pitching to other artists, committing more seriously to the band identity.

9. Facing & Accepting Rejection

[29:53-30:53]

• Open about being rejected by “every record label in town multiple times”, learning to protect themselves emotionally by focusing on fun instead of expectations.

10. Meeting Heroes & Industry Stories

[33:02-38:51]

• Ramsey tells the story of meeting Bruce Springsteen, sitting with Counting Crows’ Adam Duritz, and being treated like a peer by Springsteen after his Broadway show.

  “He made it easy to just be yourself.” —Matthew Ramsey (38:26)

• Comments on artist insecurity and the mutual recognition among creatives: “You’re still an insecure person.” (33:27)

11. Stage Adventures: Locking Eyes with Tim McGraw in the Bathroom

[49:23-50:31]

• Surreal moment meeting Tim McGraw backstage, with McGraw singing full blast in the bathroom, unfazed by Ramsey’s presence.

12. Musical Inspirations, Beginnings & Concert Memories

[51:04-53:54]

• Wide musical background: 90s grunge, The Temptations, and more.
• First concert: Huey Lewis and the News.
• “Watching people lose their minds, going, how do I do this for a living?” —Matthew Ramsey (52:54)

13. Songwriting: Process, Inspiration, and Unintentional Overlap

[54:10-56:16]

• Discussed the prevalence of accidental song similarities and being approached by other artists over unintentional overlaps.
• Ramsey likens songwriting overlap to comedy: “There’s only so many things you can write about… you’re gonna land somewhere familiar at some point.” (55:10)

14. Creative Output & Routine

[56:54-57:32]

• Ramsey writes around three times a week “at most”—not an everyday writer, unlike some band members.
• Prefers creative bursts over a strict routine.

15. Best Old Dominion Songs: Writing & Live Performance

[60:47-62:29]

• Writing: “My Heart Is a Bar” and “Written in the Sand.”
• Live: “Memory Lane” for audience energy and collective experience.

16. Reflecting on Success, Hits, and Current Goals

[63:45-65:19]

• Industry “hit” definitions are fluid; now focus is on fan connection, memorable live moments, and creative fulfillment.

17. Touring Abroad: Adjusting to Non-U.S. Crowds

[72:12-74:27]

• European tours require adapting—fans abroad are more focused on music, storytelling; less about “the party.”
• Reflects on learning to slow down, communicate differently, and appreciate cultural differences.

  “Over there, it’s more about the music, and they want to hear more talking and more stories.” —Matthew Ramsey (72:40)

Notable Quotes & Memorable Moments

• On Bandmate Wit’s Anxiety:

  “If you’re the person that is anxious and doesn’t like to talk, it shines a light on you a little bit. And people want to make him talk… It really freaks him out.” —Matthew Ramsey (05:18)

• On Turning Down Taylor Swift:

  “They needed an acoustic guitar player… I was super broke and needed the money, but ultimately decided that’s not why I moved here.” —Matthew Ramsey (01:41)

• On Creative Drive:

  “I wish I was the type of person that was cool with [normalcy].” —Matthew Ramsey (11:53)

• On Artistic Rejection:

  “We got turned down by every record label in this town multiple times… What do you want to do? We’re having a good time.” —Matthew Ramsey (26:14)

• On Meeting Bruce Springsteen:

  “He made it easy to just be yourself.” —Matthew Ramsey (38:26)

• On Performing for Small/Large Crowds:

  “We don’t care about the small part. You know, that’s natural… in America, it’s as much about the party as it is about the music… Over there, it’s more about the music, and they want to hear more talking and more stories.” —Matthew Ramsey (72:13)

• On Accepting Compliments:

  “My instinct would be to be self-deprecating when receiving a compliment, but someone explained to me it’s like someone handing you a gift and you slap it out of their hand…” —Matthew Ramsey (69:30)

• On Touring Europe and Adapting:

  “We came out for the party, and… they’re just staring at us and listening very intently… Let’s just take a step back and let’s engage with them and talk to them a little bit more.” —Matthew Ramsey (72:40)

Timestamps for Important Segments

• [05:06] — On Wit’s social anxiety and band agreement
• [11:53] — Struggles with wanting normalcy vs. creative drive
• [13:48] — Origin and concept behind “Barbara” album/title
• [16:31, 01:41] — Turning down Taylor Swift gigs
• [21:30] — Life-changing Nashville advice from Darrell Scott
• [26:59] — Old Dominion’s organic beginnings and “Break Up with Him”
• [29:53] — Processing repeated rejection, staying resilient
• [33:02] — Meeting heroes, including Bruce Springsteen and Adam Duritz
• [49:23] — Tim McGraw bathroom story
• [51:04] — Early musical influences and first concert
• [54:10] — Songwriting overlaps and artistic generosity
• [60:47] — Old Dominion’s best written and best live songs
• [63:45] — The evolving meaning of a “hit” and creative satisfaction
• [72:12] — Adapting shows for international audiences

Final Thoughts

This episode is a goldmine for fans of Old Dominion, aspiring musicians, and anyone interested in the vulnerable, behind-the-scenes realities of the music business. Through humor and honesty, Bobby and Matthew explore the balance between following passion, making tough choices, facing rejection, and building lasting artistry. Ramsey’s wisdom and self-awareness make this conversation especially resonant for anyone balancing ambition with a desire for genuine fulfillment and connection.

For tour dates and more:
weareolddominion.com

Record: “Barbara” released August 22
Tour: “How Good Is That?” World tour