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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
Social Media
Comedy
Moe Bandy

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

PublishesWeeklyEpisodes79Foundeda year ago
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Artwork for Drifting Cowboy

Latest Episodes

Tanya Tucker joins the Drifting Cowboy Podcast to tell the incredible story of how she became a superstar at just 13 years old. Tanya takes us back to the beginning of her career, signing with legendary producer Billy Sherrill, hearing “Delta Dawn” f... more

In this episode of Drifting Cowboy, Dillon Weldon sits down with The Bellamy Brothers for one of the wildest conversations yet. Howard and David Bellamy tell unbelievable stories from before and after country music fame, including growing up in Flori... more

YouTube

Ned LeDoux has new music on the way, including a brand-new music video coming soon — and in this episode, he joins Drifting Cowboy to talk about his own career, carrying on the LeDoux name, and the legacy of his father, Chris LeDoux.

Ned shares what... more

YouTube

Whey Jennings joins the Drifting Cowboy Podcast for a conversation that goes far beyond country music. As the grandson of the legendary Waylon Jennings and Jessi Colter, Whey shares never-before-heard stories about growing up in one of country music'... more

YouTube

Key Facts

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Contact Information
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Recent Guests

Ned LeDoux
Son of Chris LeDoux, drummer and musician
Musician
Episode: Chris Ledoux Was Country Music's Wildest Performer | Ned Ledoux
Whey Jennings
Country artist, son of Waylon Jennings
Musician
Episode: What Waylon Jennings Was Really Like | Whey Jennings
Jake Worthington
Country artist and podcast guest
Episode: Daryle Singletary Stopped the Show Mid-Song | Jake Worthington
Braxton Keith
Country musician focused on traditional and neo-traditional styles
Independent artist / Braxton Keith
Episode: Is Traditional Country Music Finally Back? | Braxton Keith
Clint Black
Country music artist and storyteller, breakout star of Killin Time era
Self
Episode: Why Clint Black Walked Away
Paul Cauthen
Musician and songwriter featured on the episode
Musician
Episode: Kris Kristofferson Thought I was Johnny Cash | Paul Cauthen
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

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 78 ratings
  • Engaging, deep, and funny

    Dillon has so many interesting, articulate guests. He gets deep into country music history. Hugely insightful into what is behind the art of music.

    Apple Podcasts
    5
    Stevopeach
    United Statesa month ago
  • 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 States3 months 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 States7 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 States7 months ago
  • Dillon is a great host

    Awesome guests, great stories, love this pod!

    Apple Podcasts
    5
    JohnCzech23
    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.

What Waylon Jennings Was Really Like | Whey Jennings
Q: What has been your experience of being in the industry with the Jennings name?
It's been a blessing and a curse: it opens doors but also puts you under constant scrutiny, so you have to prove you can do it as well as the predecessor while staying true to yourself.
Why Clint Black Walked Away
Q: How did writing with Merle Haggard come about, and what was that experience like?
He describes meeting Haggard, sharing a practical collaboration process where he helped finish a verse, and the experience feeling like a mentor-student dynamic that yielded a lasting fondness for the collaboration.
Why Clint Black Walked Away
Q: What was the moment you realized you had made it after ten years of playing the bars?
Clint explains that the unexpected commercial success of Killin Time and the debut album's unprecedented chart performance created both validation and enormous pressure, especially on vocal performance and touring responsibilities.
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.

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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Which podcasts are similar to Drifting Cowboy?

These podcasts share a similar audience with Drifting Cowboy:

1. TL's Road House
2. God's Country
3. Bertcast
4. This Past Weekend w/ Theo Von
5. Rodeo Time with Dale Brisby

How many episodes of Drifting Cowboy are there?

Drifting Cowboy launched a year ago and published 79 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?

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What guests have appeared on Drifting Cowboy?

Recent guests on Drifting Cowboy include:

1. Ned LeDoux
2. Whey Jennings
3. Jake Worthington
4. Braxton Keith
5. Clint Black
6. Paul Cauthen
7. Earl Peanutt Montgomery
8. Charlene Montgomery

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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