Drifting Cowboy artwork

Music Interviews · Dillon Weldon

Drifting Cowboy

by Dillon Weldon

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 country or just found it, this show brings you closer to the music and the people who lived it. New episodes every week.

Latest episodes

Showing 20 · updated from the feed

The REAL Story Behind “Long Black Train” | Josh Turner

#19 trending · Music Interviews

Josh Turner sits down with Dillon Weldon on the Drifting Cowboy Podcast to reveal the real story behind “Long Black Train”—including the powerful vision that inspired one

Sep 10
46 min

What David Allan Coe Was Really Like | His Band Tells All

#45 trending · Music Interviews

David Allan Coe’s former band members sit down to tell the wild, uncensored stories from their years on the road with one of country music’s most legendary outlaws. They

Sep 3
1 h 45 min

What George Jones Was Really Like | Nancy Jones Tells All

In this unforgettable episode of the Drifting Cowboy Podcast, Nancy Jones opens up about the real George Jones — the husband, the friend, and the man behind one of the gr

Aug 20
51 min

David Allan Coe's Lost Son Finally Speaks Out

For the first time on Drifting Cowboy, David Allan Coe’s son shares the deeply personal and heartbreaking story of growing up without a relationship with his famous fathe

Aug 13
1 h 23 min

The Roger Miller Stories Only His Son Could Tell

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 Mille

Aug 6
46 min

Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories

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 legend

Jul 30
56 min

Tanya Tucker’s Insane Rise to Stardom at Just 13 Years Old

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 he

Jul 16
1 h 07 min

The Bellamy Brothers Told Stories They Probably Shouldn’t Have

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

Jul 9
34 min

Chris Ledoux Was Country Music's Wildest Performer | Ned Ledoux

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

Jun 26
42 min

What Waylon Jennings Was Really Like | Whey Jennings

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,

Jun 18
44 min

Daryle Singletary Stopped the Show Mid-Song | Jake Worthington

Jake Worthington joins the Drifting Cowboy Podcast to share stories from the road, his rise in country music, and the legends who helped shape his career. Jake talks abou

Jun 11
53 min

Aaron Lewis Says Country Radio Blackballed Him

Aaron Lewis sits down for a raw conversation about his journey from the early days of Staind to becoming one of the most talked-about voices in country music. In this e

Jun 1
23 min

Is Traditional Country Music Finally Back? | Braxton Keith

Braxton Keith joins the Drifting Cowboy Podcast for a conversation about the resurgence of traditional country music, honky-tonks, songwriting, touring, and what it takes

May 29
47 min

Why Clint Black Walked Away

Country music legend Clint Black joins the Drifting Cowboy Podcast for one of his most revealing interviews yet. Clint opens up about his rise from Texas clubs to becomin

May 21
43 min

Kris Kristofferson Thought I was Johnny Cash | Paul Cauthen

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 heartbreakin

May 15
31 min

The Night George Jones Shot at Peanutt Montgomery

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 song

Apr 30
57 min

Vince Gill Tells the REAL Story of His Rise

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 chan

Apr 23
1 h 24 min

Gary Stewart Was WILDER Than You Think… His Inner Circle Tells All

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

Apr 16
1 h 01 min

Ronnie McDowell

Ronnie McDowell has lived one of the most fascinating careers in country music history—and in this episode of Drifting Cowboy, he tells it like only he can. From the mom

Apr 9
56 min

Hannah Dasher

In this episode of Drifting Cowboy, I sit down with rising country artist and viral sensation Hannah Dasher to talk about her journey through country music—from grinding

Mar 19
48 min

Chart trend

Position in the Music Interviews chart (US), last 90 days.

#7
all-time peak
9
days in the top 10 since Oct 2025

Chart positions

Where Drifting Cowboy ranks today in each Apple Podcasts chart (US, Sep 15, 2026).

#71 ▲ 6 Music US
#11 ▲ 1 Music Interviews US

What listeners say

A curated, balanced selection of Apple Podcasts reviews.

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.

Cash361 · Aug 2026

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

Stevopeach · Jun 2026

Just discovered this podcast. Great guests, inside stories, down home feel…love it all!!

Glen in Kokomo · Aug 2025

We strive to present a balanced view by showing a diverse range of reviews from Apple Podcasts.

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About Drifting Cowboy on Reason.fm

Here you find the Apple Podcasts chart positions of Drifting Cowboy, its latest episodes to listen to directly, and reviews from listeners. Rankings are updated daily for the United States.

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