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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
George Jones
Benjamin Tod
Merle Haggard
Grand Ole Opry
Dallas Frazier
Marcus King
Guy Clark
Bob Dylan
Addiction Recovery
Townes Van Zandt
Music Industry
Social Media
Comedy

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

PublishesWeeklyEpisodes81Foundeda year ago
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Artwork for Drifting Cowboy

Latest Episodes

Dean Miller, son of country music legend Roger Miller, joins the Drifting Cowboy Podcast to share the stories only a son could tell.

Dean opens up about what Roger Miller was really like away from the spotlight—from his unforgettable sense of humor ... more

YouTube

Johnny Cash once showed up at the Statler Brothers’ house and made biscuits—and somehow, that’s only the beginning.

Wilson Fairchild, the sons of Statler Brothers legends Don and Harold Reid, join me alongside the next generation, Jack and Davis, fo... more

YouTube

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

YouTube

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

Key Facts

Accepts Guests
Accepts Sponsors
Contact Information
Podcast Host
Number of Listeners
Find out how many people listen to this podcast per episode and each month.

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Recent Guests

Davis Reid
Langdon's son, Don Reid's grandson
Wilson Fairchild / Gaither Music
Episode: Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories
Langdon Reid
Davis Reid's brother, part of Wilson Fairchild
Wilson Fairchild / Gaither Music
Episode: Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories
Will Reid
Langdon's son, part of Wilson Fairchild
Wilson Fairchild / Gaither Music
Episode: Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories
Jack Reid
Davis and Will's cohort, Reid family member
Gaither Music / Wilson Fairchild
Episode: Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories
Tanya Tucker
Grammy-winning country artist and Country Music Hall of Famer
Episode: Tanya Tucker’s Insane Rise to Stardom at Just 13 Years Old
David Bellamy
Musician, The Bellamy Brothers
The Bellamy Brothers
Episode: The Bellamy Brothers Told Stories They Probably Shouldn’t Have
Howard Bellamy
Musician, The Bellamy Brothers
The Bellamy Brothers
Episode: The Bellamy Brothers Told Stories They Probably Shouldn’t Have
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

Host

Dillon Weldon
Host of the show, shepherding conversations with guests and guiding interview flow.

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 States2 months 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 States8 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 States8 months ago
  • Dillon is a great host

    Awesome guests, great stories, love this pod!

    Apple Podcasts
    5
    JohnCzech23
    United States8 months ago

Listeners Say

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

Listeners praise the host's ability to let guests tell their stories and to surface behind-the-scenes details.
Episodes are educational and entertaining, often highlighting the art and history behind country music.
Guests are consistently engaging and articulate, with deep country music history insights.

Chart Rankings

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

Talking Points

Recent interactions between the hosts and their guests.

Aaron Lewis Says Country Radio Blackballed Him
Q: What inspired your move into country music and how did it begin?
It started with a deep personal pull to write differently and explore storytelling that resonated with patriotism and reflection, all while bringing the rock sensibility I learned from Staind into a country framework.
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.

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?

A history-forward interview series that blends deep dives into country music's legends with behind-the-scenes storytelling. Episodes frequently center on artists' career milestones, family legacies, and the evolving music industry, offering granular anecdotes about recording, touring, mentors, and the cultural context around classic and contemporary country. A notable strength is the host's steady, conversational approach that invites players from the genre's golden era and its newest stewards to share candid memories, craft, and philosophy. This show is particularly engaging for listeners who crave authentic history, guitar-driven storytelling, and nuanced artist profiles, with occasional explorations of branding, touring life, and industr... more

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How many listeners does Drifting Cowboy get?

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To see how many followers or subscribers Drifting Cowboy has on Spotify and other platforms such as Castbox and Podcast Addict, simply upgrade your account. You'll also find viewership figures for their YouTube channel if they have one.

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. Rodeo Time with Dale Brisby
4. The Dale Jr. Download
5. Americana Podcast

How many episodes of Drifting Cowboy are there?

Drifting Cowboy launched a year ago and published 81 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. Davis Reid
2. Langdon Reid
3. Will Reid
4. Jack Reid
5. Tanya Tucker
6. David Bellamy
7. Howard Bellamy
8. Ned LeDoux

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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