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PODCAST

Drifting Cowboy

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

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All Episodes

01:23:04

David Allan Coe's Lost Son Finally Speaks Out

Drifting Cowboy ·

2026/08/13

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

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00:46:27

The Roger Miller Stories Only His Son Could Tell

Drifting Cowboy ·

2026/08/06

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

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00:56:05

Johnny Cash Made Biscuits at Our House | Wild Statler...

Drifting Cowboy ·

2026/07/30

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

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01:07:35

Tanya Tucker’s Insane Rise to Stardom at Just 13...

Drifting Cowboy ·

2026/07/16

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

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00:34:43

The Bellamy Brothers Told Stories They Probably...

Drifting Cowboy ·

2026/07/09

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

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00:42:56

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

Drifting Cowboy ·

2026/06/26

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

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00:44:35

What Waylon Jennings Was Really Like | Whey Jennings

Drifting Cowboy ·

2026/06/18

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

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00:53:50

Daryle Singletary Stopped the Show Mid-Song | Jake...

Drifting Cowboy ·

2026/06/11

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

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00:23:10

Aaron Lewis Says Country Radio Blackballed Him

Drifting Cowboy ·

2026/06/01

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

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00:47:54

Is Traditional Country Music Finally Back? | Braxton...

Drifting Cowboy ·

2026/05/29

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,

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00:43:49

Why Clint Black Walked Away

Drifting Cowboy ·

2026/05/21

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

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00:31:03

Kris Kristofferson Thought I was Johnny Cash | Paul...

Drifting Cowboy ·

2026/05/15

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

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00:57:46

The Night George Jones Shot at Peanutt Montgomery

Drifting Cowboy ·

2026/04/30

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

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01:24:26

Vince Gill Tells the REAL Story of His Rise

Drifting Cowboy ·

2026/04/23

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

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01:01:18

Gary Stewart Was WILDER Than You Think… His Inner...

Drifting Cowboy ·

2026/04/16

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

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00:56:25

Ronnie McDowell

Drifting Cowboy ·

2026/04/09

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

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00:48:22

Hannah Dasher

Drifting Cowboy ·

2026/03/19

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

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00:58:31

John Carter Cash

Drifting Cowboy ·

2026/03/12

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

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00:30:07

Ben James | The Oak Ridge Boys

Drifting Cowboy ·

2026/03/05

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

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00:29:46

Jesse Keith Whitley

Drifting Cowboy ·

2026/02/26

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

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82 results

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