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Artwork for Drifting Cowboy

Drifting Cowboy

Dillon Weldon
Country Music
Nashville
Songwriting
Waylon Jennings
Randy Travis
Texas Music Scene
Willie Nelson
Benjamin Tod
George Jones
Merle Haggard
Grand Ole Opry
Dallas Frazier
Marcus King
Guy Clark
Bob Dylan
Addiction Recovery
Townes Van Zandt
Comedy
Moe Bandy
Music Industry

The Drifting Cowboy Podcast is where country music history and storytelling collide. Hosted by Dillon Weldon, each episode dives into the legends, lost stories, and behind-the-scenes moments that shaped country music. With guests like Travis Tritt, Ray Wylie Hubbard, and Randy Travis, you'll hear real conversations that reveal the heart, humor, and history of the genre. Whether you grew up on coun... more

PublishesWeeklyEpisodes71Foundeda year ago
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Artwork for Drifting Cowboy

Latest Episodes

Country artist and storyteller Paul Cauthen joins the Drifting Cowboy Podcast for one of the most emotional conversations yet. In this episode, Paul shares a heartbreaking story about Kris Kristofferson during his later years, including the moment Kr... more

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George Jones shooting at Peanutt Montgomery sounds unbelievable—but this is the real story, told firsthand. In this episode of the Drifting Cowboy Podcast, legendary songwriter Peanutt Montgomery shares the night things went too far with George Jones... more

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n this episode of the Drifting Cowboy Podcast, Vince Gill opens up about how he REALLY became a country star. From his early days chasing a dream to the moments that changed everything, Vince shares the truth behind his rise to fame in country music.... more

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What was Gary Stewart REALLY like when the spotlight turned off?

In this episode of Drifting Cowboy, we sit down with the people who knew him best — his daughter Shannon Stewart, longtime guitarist Boogie Bob, bodyguard Terry Porter, and acclaimed b... more

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Key Facts

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Number of Listeners
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Recent Guests

Earl Peanutt Montgomery
Legendary bassist and songwriter
Musician (George Jones era)
Episode: The Night George Jones Shot at Peanutt Montgomery
Charlene Montgomery
Wife of Peanutt Montgomery
Spouse of musician
Episode: The Night George Jones Shot at Peanutt Montgomery
Vince Gill
Legendary country artist, former member of the Eagles
Episode: Vince Gill Tells the REAL Story of His Rise
Ronnie McDowell
Country/Elvis-influenced singer and painter
Episode: Ronnie McDowell
Hannah Dasher
Country artist, chef, author, and creator of Stand By Your Pan
Independent
Episode: Hannah Dasher
John Carter Cash
Musician and member of the Cash/Carter families
Cash family
Episode: John Carter Cash
Ben James
Youngest Oak Ridge Boy, new member carrying on legacy
Oak Ridge Boys
Episode: Ben James | The Oak Ridge Boys
Georgette Jones
Daughter of country music legends George Jones and Tammy Wynette
Episode: Georgette Jones
Bernie Leadon
Founding member of The Eagles and the Flying Burrito Brothers
The Eagles
Episode: Bernie Leadon (Founding Member of The Eagles)

Host

Dillon Weldon
Host of Drifting Cowboy Podcast, focused on country music history, legends, and behind-the-scenes stories.

Reviews

4.9 out of 5 stars from 67 ratings
  • Great podcast!!

    I love the podcast!

    Every guest is awesome! Every conversation is awesome!

    But!!…

    I was disappointed when I heard the host say he should know Spanish because he’s married to a Hispanic woman.

    This is America!

    If you love country music like you say you do…

    that means you love this great nation!

    The national language of the United States of America, is English.

    Apple Podcasts
    5
    theramblinggrader
    United States18 days ago
  • New around these parts

    I grew up surrounded by classic country and Tejano music. It wasn’t until I was an adult. I really fell in love with the genre and started to appreciate country music, especially classic country and country. Dylan is a master of his craft and so educational please. I recommend everyone to follow him on every platform and you will be able to obliterate any jeopardy country music category!

    Apple Podcasts
    5
    kristerz
    United States5 months ago
  • Great podcast

    What a wonderful podcast to listen to! I’m so glad I found this channel. Thank you Dillon

    Apple Podcasts
    5
    ruralroutemomma
    United States5 months ago
  • Dillon is a great host

    Awesome guests, great stories, love this pod!

    Apple Podcasts
    5
    JohnCzech23
    United States5 months ago
  • Thank You

    Dillion I just came across your podcast, wow, Duane Allen first and then William Lee Golden, ( Oaks fan since first concert in 1968, at age 10) listening to Larry Gatlin now...thank you, keep up with the great message of music...

    Apple Podcasts
    5
    Oaks68
    United States7 months ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Rich insider anecdotes and a respectful, storytelling approach that lets guests shine.
Strong history focus with a warmth from the host that invites guests to share personal stories.
Great cross-generational perspectives on country music legends and moments.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Vince Gill Tells the REAL Story of His Rise
Q: What was it like opening for Kiss in a bluegrass band?
It was chaotic and unforgettable—nobody expected us to succeed, but the experience taught me about audience dynamics, courage, and the importance of sticking to your artistry even when the crowd is hostile.
Vince Gill Tells the REAL Story of His Rise
Q: What's the story behind the song When I Call Your Name?
It emerged from a period of growth and collaboration; the right people, including management and producers, helped shape it into a career-defining record, with the right timing and a willingness to write and perform songs that felt true to me.
John Carter Cash
Q: How did the Jamaica chapters shape your family and your music?
He shares vivid memories of Cinnamon Hill, the crocodile stories, and Jamaica's influence on the family's artistic sensibilities, including the connection to island music that fed into projects like Pineapple John and broader cultural ties.
John Carter Cash
Q: What was it like growing up with such famous parents and traveling so much from a young age?
John Carter Cash describes a childhood filled with constant movement and a sense of normalcy around fame, noting a strong sense of center and community among friends, while recognizing the unique pressures and privileges of his upbringing.
Ben James | The Oak Ridge Boys
Q: How did Ben James first get involved with the Oak Ridge Boys?
Ben explains a quick, pivotal sequence—from meeting Jimmy Fortune at Hilltop Studio to being invited to sing and eventually joining the group after a short audition, turning a moment of doubt into a tangible opportunity.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

Frequently Asked Questions About Drifting Cowboy

What is Drifting Cowboy about and what kind of topics does it cover?

The show leans into deep-dish country music history, lore, and personal anecdotes from artists, songwriters, and industry insiders. Episodes center on legacy acts, pivotal studio moments, touring life, and the human side of fame, often anchored by vivid storytelling and behind-the-scenes memories. The format tends to blend archival anecdotes with candid reflections, making it appealing to listeners who enjoy listening to the evolution of country music through personal narratives and era-defining moments. A standout strength is the host's ability to let guests tell their stories with warmth and nuance, plus a knack for surfacing surprising, behind-the-scenes details that real fans appreciate. This makes it a strong pick for listeners who cra... more

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How many listeners does Drifting Cowboy get?

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Which podcasts are similar to Drifting Cowboy?

These podcasts share a similar audience with Drifting Cowboy:

1. TL's Road House
2. White Trash with Money
3. Rodeo Time with Dale Brisby
4. God's Country
5. The Dale Jr. Download

How many episodes of Drifting Cowboy are there?

Drifting Cowboy launched a year ago and published 71 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

How do I contact Drifting Cowboy?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

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What guests have appeared on Drifting Cowboy?

Recent guests on Drifting Cowboy include:

1. Earl Peanutt Montgomery
2. Charlene Montgomery
3. Vince Gill
4. Ronnie McDowell
5. Hannah Dasher
6. John Carter Cash
7. Ben James
8. Georgette Jones

To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.

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