Music

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 every week.

Latest Episodes:

Sam Williams Aug 06, 2025

Show notes

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 this isn’t just about the past.Sam is a creative force of his own, pushing boundaries and reimagining what music can be. With haunting lyrics, genre-bending style, and raw emotional honesty, Sam is proving he’s not just continuing the legacy — he’s evolving it.If you care about country music history and its future, you won’t want to miss this.Subscribe for more interviews with country legends and the voices shaping tomorrow’s sound.sam williams interview, hank williams grandson, hank williams jr son, sam williams podcast, drifting cowboy podcast, country music legacy, merle kilgore, sam williams country music, innovator in country music, sam williams music, outlaw country, new country artists, country music storytelling, sam williams 2025, country music family dynasty

Murder on Music Row: Sammy Sadler's Story Jul 28, 2025

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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 Row, country music podcast, country music history, Nashville murder, country music interviews, true crime in country music, 80s country music, country music stories, Drifting Cowboy Podcast, country music legends, Sammy Sadler interview, country music Nashville, Music Row history, country music documentary.

Jamey Johnson Jul 15, 2025

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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.

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Mac McAnally Jul 04, 2025

Show notes

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 legends—this one's for you.

🎙️ Topics Covered:

Touring and recording with Jimmy Buffett
Mac’s Southern childhood and musical roots
Stories about John Prine and Toby Keith
Songwriting insights and industry secrets

📌 Don’t forget to like, comment, and subscribe for more stories from the legends of country music!

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Special Episode: Tyler White of Love on the Spectrum Jun 27, 2025

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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 powerful moment that Tyler will never forget.This is more than just a story about music. It’s about dreams coming true, inclusion, and how a single act of kindness can ripple through an entire industry.🎙️ Hosted by Dillon Weldon (Drifting Cowboy Podcast)🎵 Featuring: Tyler White, Randy Travis, Eryn Cooper (WSM), and the Grand Ole Opry family📍 Filmed in Nashville, Tennessee💬 If this moved you, please like, comment, and share to help spread Tyler’s story to the world.#LoveOnTheSpectrum #GrandOleOpry #TylerWhite #CountryMusic #AutismAwareness #InclusionMatters #DriftingCowboyPodcast #SurpriseMoment

Lukas Nelson Jun 17, 2025

Show notes

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 next.🔥 Subscribe for more rare interviews, wild stories, and music history straight from the legends themselves.Tags: Lukas Nelson interview, Kris Kristofferson songwriting, A Star Is Born Lukas Nelson, Lukas Nelson pilot, Willie Nelson family, Lukas Nelson music, country music podcast, Drifting Cowboy, Lukas Nelson 2025, live music podcast, outlaw country stories, country music storytelling

Clay Walker May 30, 2025

Show notes

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 keeps him grounded, and what it truly means to endure in the world of country music, as well as the upcoming biopic on Randy Travis' life, where Clay will portray Randy.🎙️ Topics Covered:• Merle Haggard's emotional duet with Clay• Wild stories about George Jones and Johnny Paycheck• Clay’s MS diagnosis and life perspective• Behind-the-scenes of his biggest hits and career🔔 Subscribe for more legendary country music stories, interviews, and behind-the-scenes moments.#ClayWalker #MerleHaggard #GeorgeJones #JohnnyPaycheck #CountryMusicPodcast #DriftingCowboyPodcast #RandyTravis #movie

Cledus T. Judd May 22, 2025

Show notes

🎙️ 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 when you're pushing boundaries. Whether you’re a longtime fan or just discovering Cledus, you won’t believe the stories he shares.#CledusTJudd #MichaelJackson #CountryMusicPodcast #DonHenley #GrandOleOpry #CountryComedy #DriftingCowboyPodcast #MusicIndustry #BehindTheScenes

Ray Wylie Hubbard May 14, 2025

Show notes

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 Podcast

🔔 New episodes every week

📍 Filmed in Nashville, TN

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Chandler Walters May 06, 2025

Show notes

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 why his love for that classic Texas sound is striking a chord with a new generation. If you’re craving steel guitars, dancehall rhythm, and real storytelling with a modern twist—this episode delivers.Chandler Walters, Chandler Walters interview, Chandler Walters podcast, Chandler Walters Post Malone, Chandler Walters DeVille Records, Ernest DeVille Records, Western swing revival, modern Western swing, new country artists 2025, Post Malone country tour, Ernest country singer, rising country star, country music podcast, Nashville country music, Chandler Walters Western swing, Drifting Cowboy Podcast, traditional country music, Texas swing sound, country music 2025, Chandler Walters live tour, DeVille Records artist, country swing artist, Chandler Walters steel guitar, new Western swing artist.

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