Podcast · Music

Drifting Cowboy

by Dillon Weldon · English · Music

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 re

New episodes: Weekly
Typical length: 56 min
Latest: 1 Oct 2026
Language: English

Latest episode

1 Oct 2026 · 1 hr 9 min

Why Chet Atkins Fired Steve Wariner

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 it was really like learning from one of the greatest musicians and producers in country music history. Steve also opens up about his friendship with Jerry Reed later in Jerry’s life, sharing stories and memories of the legendary guitarist, entertainer, and songwriter. He talks about working with acclaimed producer Tony Brown, the people who…

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Earlier episodes 29 most recent

24 Sep 2026 · 1 hr 2 min
Steve Wariner Blew Jerry Reed’s Mind in Front of Chet Atkins
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 and Bob Luman, recording at Johnny Cash’s studio with Johnny Cash producing, and what it was like meeting Cash for the first time. He also tells the incredible story of meeting Chet Atkins at RCA while Jerry Reed was in the room — including the moment Steve played “I’m Already Taken” and Jerry looked at Chet and said, “Damn, Chet, sign this boy.…
10 Sep 2026 · 47 min
The REAL Story Behind “Long Black Train” | Josh Turner
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 of the most unforgettable songs in modern country music. Josh also reflects on 20 years of “Your Man” and shares the story behind the career-defining hit. He opens up about growing up surrounded by music, the vocal cord injury that left him wondering whether he would ever sing again, meeting the legendary Johnny Cash, and recording “Me and God” with bluegrass icon Ralph Stanley. From the songs that changed his life to the…
3 Sep 2026 · 1 hr 46 min
What David Allan Coe Was Really Like | His Band Tells All
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 reveal what David was really like behind the scenes—the chaos, humor, music and unforgettable moments that never made it into the official story. Joining the conversation are renowned Nashville songwriters Gary Gentry, who wrote David Allan Coe’s classic hit “The Ride,” and Bobby Keel, who wrote “Time Off for Bad Behavior.” Together, they revisit the songs, characters and unbelievable road stories surrounding one of the most…
20 Aug 2026 · 51 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 greatest voices in country music history. Nancy shares deeply personal stories from their marriage, including the turbulent years, George’s battle with addiction, how she helped him get sober, and the life they built together away from the spotlight. Nancy also takes us inside George Jones’ friendships with fellow country music legends including Waylon Jennings, Johnny Cash, Johnny Paycheck , and others who were part of their…
13 Aug 2026 · 1 hr 23 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 father and spending years hoping for the chance to finally connect with him.David Allan Coe became one of the most controversial, influential and unmistakable figures in outlaw country music, writing and recording songs that helped define an era. But behind the music, fame and legendary stories was a complicated family life that few people outside the Coe family ever truly knew.In this emotional conversation, David Allan Coe’s…
6 Aug 2026 · 46 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 Miller was really like away from the spotlight—from his unforgettable sense of humor and unpredictable antics to the friendships, struggles, and creative brilliance behind one of country music’s most original careers. He also shares personal stories involving Johnny Cash, Willie Nelson, and other legendary figures who crossed paths with Roger throughout his life. Roger Miller changed country music with songs like “King of the…
30 Jul 2026 · 56 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 legends Don and Harold Reid, join me alongside the next generation, Jack and Davis, for an episode packed with hilarious, unbelievable country music history. They share stories about growing up around the Statler Brothers, Johnny Cash cooking at their house, a wild night in a Canadian jail, Roy Acuff stealing catered food from their television show, and plenty more that has rarely—if ever—been told publicly. This is more than an…
16 Jul 2026 · 1 hr 8 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 her career, signing with legendary producer Billy Sherrill, hearing “Delta Dawn” for the first time, and experiencing a rise to fame that happened almost overnight. She also shares stories about her friendship with David Allan Coe and how he pitched her “Would You Lay with Me (In a Field of Stone),” meeting Gary Stewart and Dean Dillon, writing “Leave Them Boys Alone,” appearing in Jeremiah Johnson , and navigating country…
9 Jul 2026 · 35 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 stories from before and after country music fame, including growing up in Florida, trying to survive before the hits, living in Jim Stafford’s basement with comedian Gallagher , and the crazy road stories that came with touring alongside legends like Conway Twitty, Merle Haggard, George Jones , and more. From “Let Your Love Flow” to decades of life on the road, The Bellamy Brothers open up about the outlaw side of country…
26 Jun 2026 · 43 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 on the LeDoux name, and the legacy of his father, Chris LeDoux. Ned shares what it was really like growing up on the road with Chris LeDoux — rodeo champion, country music legend, and one of the most electric live performers to ever step on a stage. In this conversation, Ned tells stories from inside Chris LeDoux’s band, from mechanical bulls and pyrotechnics on stage to the wild energy of those legendary concerts. He also…
18 Jun 2026 · 45 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, Whey shares never-before-heard stories about growing up in one of country music's most iconic families, what Waylon was really like behind closed doors, and the legacy that still follows the Jennings name today. We also dive into Whey's own journey through addiction, hitting rock bottom, getting sober, and building a music career on his own terms. From family stories and outlaw country history to redemption, faith, and…
11 Jun 2026 · 54 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 about opening for Daryle Singletary, the unforgettable night Daryle stopped a show over a wrong note, lessons learned from Marty Stuart, working with Miranda Lambert, his experience on The Voice, and why traditional country music still matters. From hilarious backstage moments to honest conversations about country music's past and future, this is one of the most entertaining Jake Worthington interviews you'll hear.If you enjoy…
1 Jun 2026 · 23 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 episode, Aaron opens up about how Staind began, what changed when he went from rock star to country artist, and why he believes country radio stopped supporting his music after he became outspoken about politics. Aaron also shares stories about his friendship with Charlie Daniels, the making of “Country Boy” with Charlie Daniels and George Jones, and what it was like bringing rock, country, and real-life conviction into the…
29 May 2026 · 48 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 to build a fanbase in today's music industry. Braxton shares his thoughts on classic country influences, the current state of Nashville, the growing demand for authentic country music, and why so many young fans are embracing traditional sounds again. If you're a fan of George Strait, Alan Jackson, Randy Travis, Zach Top, Cody Johnson, and classic country music, this is an episode you won't want to miss.🔔 Subscribe for more…
21 May 2026 · 44 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 becoming the biggest debut in country music history, why he ultimately walked away from RCA Records, and the battles over creative control that changed his career forever. Clint also shares incredible stories about Merle Haggard, Waylon Jennings, Jimmy Buffett, songwriting, the Nashville machine, and the era that changed country music forever. Plus, he discusses his brand-new book and reflects on the highs, pressures, and realities…
15 May 2026 · 31 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 heartbreaking story about Kris Kristofferson during his later years, including the moment Kris believed he was speaking to Johnny Cash. Paul also talks about his family’s connection to Hank Williams, outlaw country music, songwriting, life on the road, and the legends that shaped country music history. If you love classic country stories, rare behind-the-scenes moments, and deep conversations about the artists who built country music,…
30 Apr 2026 · 58 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 songwriter Peanutt Montgomery shares the night things went too far with George Jones, along with a lifetime of wild, unforgettable moments from inside country music.Peanutt also dives into meeting Elvis Presley, writing songs with Loretta Lynn, and what it was like when Tanya Tucker lived with them during her early years. From the golden era of country music to the chaos behind the scenes, these are the stories you don’t hear…
23 Apr 2026 · 1 hr 24 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 changed everything, Vince shares the truth behind his rise to fame in country music.This isn’t the polished version you’ve heard before. Vince talks about the struggles, the turning points, and what it actually takes to make it in the country music world. If you’ve ever wondered how legends are made—and what it costs—this is the story.Vince Gill is one of the most respected voices in country music history, with countless hits,…
16 Apr 2026 · 1 hr 1 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 Stewart, longtime guitarist Boogie Bob, bodyguard Terry Porter, and acclaimed biographer Jimmy McDonough — for an unfiltered look at one of country music’s most misunderstood legends. They share never-before-heard stories about Gary’s wild lifestyle, his struggles, his sense of humor, and the moments that defined him behind the scenes. From chaotic nights on the road to unforgettable pranks and the reality of his battles…
9 Apr 2026 · 56 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 moment he released “The King Is Gone” as a tribute to Elvis Presley, Ronnie’s life changed forever. That song launched a career that would go on to include massive hits like “Older Women” and “Wondering Eyes,” along with decades of stories from inside the heart of country music. In this conversation, Ronnie opens up about his friendships and experiences with legends like Conway Twitty and George Jones—sharing stories you won’t…
19 Mar 2026 · 48 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 it out as a Nashville songwriter to breaking through as an artist and building a massive audience with her “Stand By Your Pan” cooking series. Hannah shares what it really takes to make it in today’s music industry, how she carved out her own lane, and the moments that changed everything for her career. Along the way, she tells incredible stories about country legends like Patsy Cline, Naomi Judd, and what it was like…
12 Mar 2026 · 59 min
John Carter Cash
John Carter Cash joins the Drifting Cowboy Podcast to share what his parents, Johnny Cash and June Carter Cash , were really like behind the scenes. As the only son of two of the most iconic figures in country music history, John Carter offers a rare and personal look at the lives, personalities, humor, struggles, and faith of the legendary couple. From growing up surrounded by music at the Cash home to witnessing his parents’ love story up close, this conversation reveals the human side of the Man in Black and the Carter Family icon that most fans never saw. In this episode, John Carter…
5 Mar 2026 · 30 min
Ben James | The Oak Ridge Boys
The Oak Ridge Boys have one of the most legendary careers in country music history, but now the group has entered a brand-new chapter. In this episode of the Drifting Cowboy Podcast, Dillon Weldon sits down with Ben James, the newest member of the Oak Ridge Boys, to talk about how he joined the iconic group and what the future looks like.Ben shares the incredible story of how he became the new Oak Ridge Boy, what it’s like stepping into a legendary group with decades of history, and what fans can expect moving forward. We also talk about Ben’s musical background, the legacy of the Oak Ridge…
26 Feb 2026 · 30 min
Jesse Keith Whitley
There may be music from Keith Whitley that the world has never heard.In this powerful conversation, Jesse Keith Whitley opens up about his father’s legacy, the possibility of unreleased recordings, and what country fans have been wondering for decades.But this episode goes far beyond that.Jesse speaks candidly about growing up as the son of two country music icons, his relationship with Lorrie Morgan, his own journey through addiction and recent sobriety, and what it’s like carving out a career under one of the most legendary names in country music history. He also shares stories involving…
20 Feb 2026 · 1 hr 10 min
Rodney Crowell
Rodney Crowell was there.Before the myth. Before the legend. Before the Outlaw era became a T-shirt.In this episode of Drifting Cowboy, Rodney Crowell reflects on his time inside one of the most influential circles in country music history — alongside Johnny Cash, Guy Clark, Townes Van Zandt, Jerry Jeff Walker, Rosanne Cash, and the writers who shaped an entire generation.From the raw reality of the Outlaw movement to the deeply human moments behind the music, Rodney shares what it was really like in the rooms where these songs — and these legends — were born. We talk about songwriting,…
12 Feb 2026 · 59 min
Rick Trevino
Rick Trevino was one of the defining voices of 90s country music. With major radio hits, national tours, and a presence during one of country’s biggest boom periods, he lived the life many artists dream about. But at the height of the era, something shifted. In this episode of Drifting Cowboy , Rick Trevino reflects on the rise of 90s country, the pressure of fame, navigating Nashville as a bilingual/Latino artist, and the pull that brought him back to his roots. He opens up about identity, industry expectations, touring during the golden era of country radio, and what it really felt like…
5 Feb 2026 · 1 hr 11 min
Bobby Bare
Bobby Bare doesn’t just remember country music history — he helped shape it.In this rare, in-depth interview, Bobby Bare reflects on a career that places him at the center of country music’s most important moments. From his role in the early creative culture that helped influence the Fender Stratocaster, to discovering and supporting artists like Waylon Jennings and Billy Joe Shaver, to firsthand stories involving Johnny Cash, Tom T. Hall, and Chet Atkins, this conversation captures living history from one of the genre’s most influential figures.Bobby shares stories you don’t hear in…
22 Jan 2026 · 36 min
John Ford Coley
Most people know Dan Seals as a country music legend — but before the hits on country radio, he was England Dan , one half of the massively successful duo England Dan & John Ford Coley . In this episode of the Drifting Cowboy Podcast , John Ford Coley sits down with me to tell the real story behind his partnership with Dan Seals, the rise of England Dan & John Ford Coley , and the honest, human reasons the duo ultimately broke up. John opens up about Dan’s transition into country music stardom, life after the split, and what it was really like navigating success at the height of the 1970s…
15 Jan 2026 · 1 hr 5 min
Gary Gentry
What really inspired “The Ride” — one of the most haunting songs in country music history?Songwriter Gary Gentry (“The Ride,” “The One I Loved Back Then,” and more) tells the unbelievable true story behind the song that has puzzled and fascinated fans for decades. After a night of heavy drinking, drugs, and reckless curiosity, Gary and a group of friends held a seance to provoke the spirit of Hank Williams.What happened next would stay with Gary forever.In this podcast, Gary recounts seeing what he believes was Hank Williams’ ghost — an encounter that later shaped the writing of “The Ride,”…

About Drifting Cowboy

Drifting Cowboy is a English music podcast from Dillon Weldon. Melo plays each episode straight from the publisher's own feed — no ads added, no account needed — and remembers where you stopped, in this browser only.

Publisher: Dillon Weldon
Language: English
Category: Music
New episodes: Weekly
Typical length: 56 min
Latest episode: 1 Oct 2026
Feed: RSS — paste into any podcast app
Apple Podcasts: podcasts.apple.com/podcast/id1813731646
Rights: Dillon Weldon

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