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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

music music interviews

All Episodes

01:29:13

Shooter Jennings

Drifting Cowboy ·

2025/09/17

Shooter Jennings joins the Drifting Cowboy Podcast for an unfiltered conversation about his father Waylon Jennings, the spirit of Outlaw Country, and the legacy that still shakes Nashville today. We dive into never-before-heard stories about Waylon and Jessi Colter, reflections on Johnny Cash, and the future of artists like Charley Crockett who are carrying the torch. Shooter also gives insight into the new Waylon albums and what they mean for fans of real country music.This episode is packed with

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01:09:15

William Lee Golden of The Oak Ridge Boys

Drifting Cowboy ·

2025/09/03

Step inside the life and legacy of William Lee Golden—the legendary Oak Ridge Boy with the iconic beard. In this exclusive conversation, we dive into untold stories of the Oak Ridge Boys, behind-the-scenes moments from country music history, the making of classic hits, and the family project that’s redefining his career, The Goldens.We talk about his brand-new book, his time on the road, and even how The Dukes of Hazzard crossed paths with the Oaks. From timeless gospel harmonies to rowdy country

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00:32:29

Ben and Noel Haggard

Drifting Cowboy ·

2025/08/27

In this episode of Drifting Cowboy, I sit down with Ben and Noel Haggard—sons of the legendary Merle Haggard—for an unforgettable conversation filled with stories, laughs, and behind-the-scenes memories. We talk about their father’s legacy, growing up in the shadow of a country music giant, and their personal experiences with icons like Kris Kristofferson and The Eagles. From road tales to rare family insights, this episode is a treasure chest for any true country music fan.If you love country music

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01:04:40

Keith Stegall, Roger Murrah and Jim McBride

Drifting Cowboy ·

2025/08/20

Alan Jackson’s career wouldn’t be the same without Keith Stegall, Roger Murrah, and Jim McBride—the powerhouse trio behind some of his biggest hits. From “Chattahoochee” and “Don’t Rock the Jukebox” to “Chasin’ That Neon Rainbow,” “Dallas,” and more, these men helped shape one of the greatest careers in country music.In this episode of Drifting Cowboy, I sit down with these legends to talk about:✅ The stories behind Alan’s iconic songs✅ How they met and began working with Alan✅ Keith Stegall’s role

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01:42:11

Larry Gatlin

Drifting Cowboy ·

2025/08/13

Country music legend Larry Gatlin sits down with Dillon Weldon for an unforgettable conversation about his decades-long career, songwriting with his brothers, behind-the-scenes Opry stories, and the wild ride from Texas honky-tonks to the Grand Ole Opry stage. Hear Larry like you’ve never heard him before — full of heart, humor, and country music wisdom. If you love real stories from the legends themselves, this one’s a must-listen.Larry Gatlin, Larry Gatlin interview, Gatlin Brothers, Larry Gatlin

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00:48:17

Sam Williams

Drifting Cowboy ·

2025/08/06

Full Interview with Sam Williams | The Drifting Cowboy PodcastIn this episode of The Drifting Cowboy, Sam Williams — grandson of Hank Williams and son of Hank Jr. — sits down for an unforgettable conversation about life, legacy, and blazing his own trail in country music. Sam opens up about the pressure of carrying the Williams name, the wisdom passed down from his legendary father and grandfather, and his relationship with Merle Kilgore, co-writer of “Ring of Fire” and longtime family friend. But

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00:26:33

Murder on Music Row: Sammy Sadler's Story

Drifting Cowboy ·

2025/07/28

In this powerful episode, country artist Sammy Sadler opens up about his remarkable career, the infamous "Murder on Music Row", and how the tragic event changed the course of his life. From his rise in the '80s country scene to surviving one of Nashville’s darkest moments, Sammy shares raw insights, untold stories, and what’s next in his musical journey. Don’t miss this emotional and revealing conversation with one of country music’s most resilient voices.Sammy Sadler, Murder on Music

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01:12:27

Jamey Johnson

Drifting Cowboy ·

2025/07/15

Jamey Johnson joins Dillon Weldon for one of his funniest and most candid interviews to date. They swap stories about Hank Cochran, Dean Dillon, Willie Nelson, and Toby Keith, and Jamey shares hilarious behind-the-scenes moments from his wild journey through country music. It’s a rare glimpse into the lighter side of one of the genre’s most respected voices.Hit that like button, subscribe, and let us know your favorite story in the comments!#JameyJohnson #CountryMusicPodcast #OutlawCountry

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01:13:54

Mac McAnally

Drifting Cowboy ·

2025/07/04

In this episode of the Drifting Cowboy Podcast, legendary songwriter and musician Mac McAnally shares wild behind-the-scenes stories from life on the road with Jimmy Buffett, his early days growing up in Mississippi, and how he first got into music. Mac opens up about his close friendship with Buffett, memories of country icons like John Prine and Toby Keith, and the songwriting journey that led to countless hits. If you're a fan of heartfelt stories, classic songwriting, and country music

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00:21:21

Special Episode: Tyler White of Love on the Spectrum

Drifting Cowboy ·

2025/06/27

Tyler White, best known for his appearance on Love on the Spectrum, had no idea that agreeing to do a podcast would lead to the biggest surprise of his life — a moment on the Grand Ole Opry stage.This documentary-style special of the Drifting Cowboy podcast takes you behind the scenes of a once-in-a-lifetime journey: from a heartfelt podcast conversation to a standing ovation at country music’s most sacred stage.You’ll witness the raw emotion, the nerves, the music, and the magic — all building to a

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00:45:14

Lukas Nelson

Drifting Cowboy ·

2025/06/17

Lukas Nelson joins the Drifting Cowboy podcast for an unforgettable conversation. He shares the moment Kris Kristofferson told him, “You have no choice but to write songs,” and opens up about the weight of legacy, songwriting, and forging his own path in music. Lukas also talks about working on A Star Is Born, becoming a licensed pilot, and even plays a little music live during the show.🎙️ Hear stories about growing up as Willie Nelson’s son, country music legends, and what Lukas has planned

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01:15:04

Clay Walker

Drifting Cowboy ·

2025/05/30

In this episode of the Drifting Cowboy Podcast, Clay Walker sits down with Dillon to share deeply personal and never-before-heard stories from his legendary country music career.From the emotional moment when Merle Haggard broke down in tears on stage, to wild memories with George Jones and Johnny Paycheck, Clay gives an unfiltered look at the legends of country music — and the real-life moments that shaped them.Clay also opens up about his ongoing battle with multiple sclerosis, the faith that

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01:12:39

Cledus T. Judd

Drifting Cowboy ·

2025/05/22

🎙️ In this explosive episode, country comedy legend Cledus T. Judd opens up like never before. From getting hit with cease and desist letters from Michael Jackson and Don Henley, to battling frostbite during his early days, his friendship with Toby Keith, and having his heart broken by the Grand Ole Opry — this is the raw, unfiltered story behind country music’s most beloved parody artist.We dive deep into the highs and lows of his caree, and what it really takes to survive in the music industry

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01:01:48

Ray Wylie Hubbard

Drifting Cowboy ·

2025/05/14

Ray Wylie Hubbard sits down for a raw, unfiltered conversation about the legendary outlaw country era — sharing personal stories about Willie Nelson, Waylon Jennings, Townes Van Zandt, Guy Clark, Blaze Foley, and Jerry Jeff Walker.From the chaos of the road to the poetry of songwriting, Ray reveals what really went down during country music’s most untamed era.👉 Don’t forget to like, comment, and subscribe for more untold country stories from the people who lived them.🎙️ The Drifting Cowboy

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00:32:46

Chandler Walters

Drifting Cowboy ·

2025/05/06

In this episode of the Drifting Cowboy Podcast, rising country artist Chandler Walters joins the show to talk about the wild ride he’s on—opening for Post Malone this summer and signing with Ernest’s new label, DeVille Records. But beyond the headlines, Chandler is doing something rare in today’s country music scene: he’s bringing back Western swing in a big way, blending tradition with fresh energy and style.We dive into how he got here, what it’s like working with major names in the industry, and

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02:11:18

Travis Tritt

Drifting Cowboy ·

2025/04/29

🎙️ Country legend Travis Tritt joins Dillon Weldon on the Drifting Cowboy Podcast for a powerful and unfiltered conversation about music, fame, family, and staying true to your roots. In this exclusive full-length interview, Tritt opens up about his outlaw image, his biggest hits, working with legends, and what he thinks about the state of country music today.Whether you're a longtime Travis Tritt fan or just love real country music stories, this episode is packed with behind-the-scenes moments,

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00:47:52

Don Goodman

Drifting Cowboy ·

2025/04/16

In this episode of the Drifting Cowboy Podcast, legendary songwriter Don Goodman takes us on a journey through his incredible career—writing songs that have saved lives, shaped country music, and stood the test of time. From penning timeless hits like Angels Among Us to co-writing Ol’ Red, Goodman shares powerful stories from behind the scenes in Nashville, including a wild moment involving Janis Joplin, a run-in with the law, and how a jail sentence became inspiration for one of country music’s

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00:46:03

Grayson Russell

Drifting Cowboy ·

2025/04/12

🎙️ On this episode of The Drifting Cowboy podcast, Dillon Weldon sits down with actor and country artist Grayson Russell—his close friend and one of Nashville’s rising stars. You know Grayson from his unforgettable roles in Talladega Nights: The Ballad of Ricky Bobby, the Diary of a Wimpy Kid series, and starring alongside Tom Hanks in the World War II drama Greyhound.In this exclusive conversation, Dillon and Grayson dive into everything from Hollywood behind-the-scenes stories to Grayson’s

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00:14:34

Ian Flanigan

Drifting Cowboy ·

2025/04/11

About This EpisodeIn this episode of Drifting Cowboy, Dillon Weldon sits down with powerhouse vocalist and The Voice finalist Ian Flanigan for an in-depth conversation about life, music, and staying grounded while chasing big dreams. Known for his gravel-rich voice and soulful songwriting, Ian shares how his time on The Voice changed his life—and how he's stayed true to his sound ever since.We talk about his journey from playing bar gigs to performing on national television, working with Blake

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00:08:11

Billie Jo Jones

Drifting Cowboy ·

2025/04/10

About This EpisodeOn this episode of Drifting Cowboy, Dillon Weldon welcomes country singer and songwriter Billie Jo Jones, whose honest lyrics and throwback sound are turning heads across the country music scene. Billie Jo shares her journey from small-town beginnings to becoming one of the freshest voices in traditional country, all while staying true to her roots.We dig into her songwriting process, her biggest musical influences, and what it's like being an independent artist carving her own

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