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 as Alan’s longtime producer
✅ Memories from the early days of Alan’s career
✅ The impact Alan Jackson made on country music
If you love country music history, songwriting stories, and behind-the-scenes insight into Alan Jackson’s rise to fame—you won’t want to miss this one.
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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.
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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
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 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!
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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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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 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
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
🎙️ 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 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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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.
🎙️ 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, laughs, and raw truth from one of the genre’s most iconic voices.🪕 Watch now and hear Travis Tritt like you've never heard him before.Travis Tritt interview, Travis Tritt podcast, country music podcast, Drifting Cowboy podcast, outlaw country, 90s country stars, Travis Tritt Nashville, Travis Tritt full interview, behind the scenes country music, Dillon Weldon
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 most iconic prison songs.We cover it all—his rise in the industry, the emotional weight behind his biggest songs, his advocacy work for veterans, and what it truly means to write songs that matter. If you love country music and the stories behind the songs, this one’s a must-listen.Don Goodman songwriter, Don Goodman interview, Don Goodman country music, Angels Among Us songwriter, Ol’ Red songwriter, country music history, Nashville songwriter stories, behind the music country, country songwriting legends, Janis Joplin story, country music podcast, Drifting Cowboy Podcast, outlaw country stories, Music Row history, real country music, 90s country hits, Nashville songwriting scene, Don Goodman Ol’ Red, Songwriters Hall of Fame, veterans and country music, stories behind country songs.
🎙️ 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 evolving career in country music and life in Nashville. Hear what it was like working with legends like Will Ferrell and Tom Hanks, and how Grayson balances the spotlight with staying true to his southern roots.
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About This Episode
In 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 Shelton, touring across the country, and the stories behind his latest music. Ian also opens up about fatherhood, perseverance, and what it means to create music that truly connects with people.
Whether you discovered Ian on The Voice or through his heartfelt original songs, this episode gives you a deeper look at the man behind the music.
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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 path.If you love real country music with grit, twang, and heart—you’ll love this conversation.Billie Jo Jones interview, country music podcast, traditional country artist, women in country music, Drifting Cowboy podcast, independent country singer, Billie Jo Jones podcast, country music storytelling, real country music, Dillon Weldon interview, Ray Price, Loretta Lynn
About This Episode
In this special episode of Drifting Cowboy, Dillon Weldon sits down with rising country music star Makenzie Phipps for a heartfelt and revealing conversation. Known for her traditional country sound and powerful vocals, Makenzie opens up about her journey in the music industry, the stories behind her songs, her Appalachian roots, and what it takes to make it in Nashville today.
We talk about everything from her viral performances and love for classic country to the challenges facing young women in the genre. If you're a fan of authentic country music, raw storytelling, and behind-the-scenes insights from tomorrow’s stars, this episode is a must-listen.
🎙️ Whether you’re a longtime supporter or new to Makenzie’s music, you’ll walk away knowing why she’s one of the most talked-about voices in country music today.
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Step back in time with The Malpass Brothers on the Drifting Cowboy podcast! In this episode, Dillon Weldon sits down with the traditional country music duo keeping the spirit of classic country alive. From their musical roots and influences like Merle Haggard and Johnny Cash, to their hilarious stories from the road and life behind the scenes, this conversation is full of heart, humor, and honky-tonk soul.
Whether you're a fan of old-school country, bluegrass, or just love great storytelling, this episode delivers an authentic slice of Americana you won't find anywhere else. Subscribe now and don't miss this unforgettable chat with The Malpass Brothers — the keepers of country music tradition.
🎙️ Drifting Cowboy — The Voice of Country Music
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In this episode, I sit down with country music legend and the King of Cheating Songs, Moe Bandy. We talk about his friendships with folks like Joe Stampley and Lefty Frizzell, his hits like Bandy the Rodeo Clown and Just Good Ol' Boys and campaigning for the Bushes. Enjoy!
