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Artwork for Drifting Cowboy

Drifting Cowboy

Dillon Weldon
Country Music
Nashville
Songwriting
George Jones
Waylon Jennings
Randy Travis
Texas Music Scene
Willie Nelson
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

PublishesWeeklyEpisodes89Foundeda year ago
Number of ListenersCategories
Music InterviewsMusic

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Artwork for Drifting Cowboy

Latest Episodes

Country music legend and 15-time GRAMMY Award winner Ricky Skaggs joins the Drifting Cowboy Podcast for an unforgettable conversation about his extraordinary journey from a young Kentucky bluegrass prodigy to one of the biggest stars in country music... more

YouTube

What were Conway Twitty and Loretta Lynn REALLY like behind the scenes? In this episode of the Drifting Cowboy Podcast, legendary country music booking agent Jimmy Jay joins us alongside his sons, Jerry Jay and Jeff Jay, to share incredible firsthand... more

YouTube

Here is part two of Steve Wariner's Drifting Cowboy episode where he tells the hilarious story of Chet Atkins "firing" him after Steve scored a big hit. Steve explains how his success as a solo artist changed his role in Chet’s band, and shares what ... more

YouTube

Hey Drifters!In Part 1 of this Drifting Cowboy conversation, Steve Wariner takes us back to the very beginning of his career and the unbelievable run of people who helped shape him before the hits ever came.Steve talks about playing with Dottie West ... more

YouTube

Key Facts

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Recent Guests

Ricky Skaggs
Country and bluegrass musician, singer, and 15-time Grammy Award winner
Ricky Skaggs
Episode: Ricky Skaggs Reveals What Keith Whitley Was Really Like
Jimmy Jay
Country music booking agent and independent promoter who represented Conway Twitty and Loretta Lynn
Jason Promotions
Episode: What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
Jerry Jay
Country music agent and promoter who worked with Conway Twitty and Randy Travis
Jason Promotions
Episode: What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
Jeff Jay
Country music promoter who worked with Randy Travis and Conway Twitty
Jason Promotions
Episode: What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
Steve Wariner
Guitarist and country artist
Episode: Why Chet Atkins Fired Steve Wariner
Josh Turner
Country music singer-songwriter known for Long Black Train and Your Man
Country Music
Episode: The REAL Story Behind “Long Black Train” | Josh Turner
David Wade
Former David Allan Coe band member and songwriter
David Allan Coe Band
Episode: What David Allan Coe Was Really Like | His Band Tells All
Ken Madsen
Co-managed David Allan Coe; involved in his last album
David Allan Coe Band
Episode: What David Allan Coe Was Really Like | His Band Tells All
George Gray Wolf
Roadie/security, long-time associate of Coe
David Allan Coe Band
Episode: What David Allan Coe Was Really Like | His Band Tells All

Host

Dillon Weldon
Host of the Drifting Cowboy Podcast and primary interviewer

Reviews

4.9 out of 5 stars from 186 ratings
  • Awesome podcast!

    I love Country music, and to hear the stories from the artists, and family members is awesome! This is by far my favorite podcast! Keep up the good work!

    Apple Podcasts
    5
    Ricky Del
    United Statesa month ago
  • Even an old-timer like me likes this

    I’m 77 and really enjoy the musicians I’m familiar with. He does a fine job. Very well informed and very empathetic with his guests.doesn’t dodge the hard questions but knows how to ask them.

    Apple Podcasts
    4
    Cash361
    United States3 months ago
  • 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 States5 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 States6 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 States10 months ago

Listeners Say

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

Guest selection and behind-the-curtain stories are highlighted as a strength.
Listeners praise deep, insightful histories of country music and the host's empathetic interviewing style.
The host's balance of humor and rigorous questioning is frequently noted as a standout quality.

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 Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
Q: How did the family handle an artist not showing up for a concert?
Jimmy Jay says they told audiences the truth, gave them time to decide whether to stay, and offered longer sets from the artists who did appear. In one weekend without Merle Haggard, George Jones and Conway Twitty performed extra-long shows, with only a small number of refunds reported for one date.
What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
Q: What was Conway Twitty really like behind the scenes?
The Jays describe him as a kind, caring, ordinary person who was known offstage as Harold Jenkins and treated Conway Twitty as a separate stage persona. They also recount his generosity toward a bedridden fan and say he did not drink or use drugs.
Ricky Skaggs Reveals What Keith Whitley Was Really Like
Q: What was he like as a kid?
Skaggs remembers Keith Whitley as a prankster who loved joking and laughing, and shares a story about Whitley persuading a bandmate to eat ten hot dogs after a bet.
Ricky Skaggs Reveals What Keith Whitley Was Really Like
Q: How did you get to get that spot?
Ricky Skaggs says Earl Scruggs saw him playing backstage at the Opry, praised his ability, and invited him to audition for the Flatt and Scruggs television show.
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.

Audience Metrics

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

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Frequently Asked Questions About Drifting Cowboy

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

The show leans into country music history and storytelling, delivering longform conversations with musicians, road crews, and industry insiders. Episodes mix origin stories, backstage anecdotes, studio memories, and era-spanning perspectives, often anchored by the host's respectful curiosity and humor. A standout trait is the emphasis on behind-the-scenes moments and lineage within country, giving listeners a sense of immersion in the people and history that shaped the genre.

What makes it distinctive is the willingness to explore both legendary careers and less-told narratives—family legacies, tours, and era-shaping moments—through candid, unscripted conversations. The format seems especially helpful for potential guests or sponsors seeki... 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. The Justin "Danger" Nunley Podcast
4. The Jarrod Morris Vibe
5. The Dale Jr. Download

How many episodes of Drifting Cowboy are there?

Drifting Cowboy launched a year ago and published 89 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.

Where can I see ratings and reviews for Drifting Cowboy?

Rephonic pulls ratings and reviews for Drifting Cowboy from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.

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What guests have appeared on Drifting Cowboy?

Recent guests on Drifting Cowboy include:

1. Ricky Skaggs
2. Jimmy Jay
3. Jerry Jay
4. Jeff Jay
5. Steve Wariner
6. Josh Turner
7. David Wade
8. Ken Madsen

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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