
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
| Publishes | Weekly | Episodes | 71 | Founded | a year ago |
|---|---|---|---|---|---|
| Number of Listeners | Categories | Music InterviewsMusic | |||

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
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
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
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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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.
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!
What a wonderful podcast to listen to! I’m so glad I found this channel. Thank you Dillon
Awesome guests, great stories, love this pod!
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...
Key themes from listener reviews, highlighting what works and what could be improved about the show.
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #19 | |
Apple Podcasts | #95 | |
Apple Podcasts | #12 | |
Apple Podcasts | #62 | |
Apple Podcasts | #77 | |
Apple Podcasts | #87 |
Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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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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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
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.
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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
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