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Drifting Cowboy

Podcast by Dillon Weldon

English

Culture & leisure

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About 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.

All episodes

72 episodes

episode Why Clint Black Walked Away artwork

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 of becoming one of the biggest stars of the 1990s. This is Clint Black like you’ve rarely heard him before — honest, reflective, funny, and completely unfiltered. #ClintBlack #CountryMusic #MerleHaggard #WaylonJennings #JimmyBuffett #90sCountry #OutlawCountry #Nashville #CountryMusicPodcast #DriftingCowboy clint black, clint black interview, why clint black walked away, clint black rca records, clint black podcast, drifting cowboy podcast, country music podcast, merle haggard stories, waylon jennings stories, jimmy buffett stories, clint black new book, 90s country music, outlaw country, country music legends, nashville music, country music history, killin time clint black, clint black songs, classic country music, george strait, alan jackson, country music interviews, country singer podcast, texas country music, merle haggard, waylon jennings, jimmy buffett

21 May 2026 - 43 min
episode Kris Kristofferson Thought I was Johnny Cash | Paul Cauthen artwork

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, this episode is for you. kris kristofferson, johnny cash, paul cauthen, hank williams, country music podcast, drifting cowboy podcast, outlaw country, classic country music, kris kristofferson interview, johnny cash stories, country music history, hank williams stories, country legends, nashville podcast, texas country music, songwriter stories, old country music, willie nelson, waylon jennings, merle haggard, country music interviews, music history, kris kristofferson lyme disease, paul cauthen interview, johnny cash podcast, country music documentary, country music fans, americana music, red dirt country, country storytelling

15 May 2026 - 31 min
episode The Night George Jones Shot at Peanutt Montgomery artwork

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 anywhere else—raw, honest, and straight from the people who lived them.If you love country music history, outlaw stories, and behind-the-scenes moments from legends like George Jones, Elvis Presley, Loretta Lynn, and Tanya Tucker, this episode is packed with it.Subscribe for more untold country music stories, legendary interviews, and deep dives into the artists who shaped the genre.george jones shot at peanutt montgomery, peanutt montgomery interview, george jones story, george jones gun story, country music stories, outlaw country stories, elvis presley meeting story, loretta lynn songwriting, tanya tucker early life, drifiting cowboy podcast, country music podcast, nashville stories, classic country legends, behind the music country, songwriting stories, honky tonk history, country music history, george jones controversy, peanutt montgomery songs, meeting elvis presley story, loretta lynn interview, tanya tucker story, outlaw country podcast, country music interviews, music legends podcast

30 Apr 2026 - 57 min
episode Vince Gill Tells the REAL Story of His Rise artwork

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, awards, and decades of influence. But behind the success is a journey most people never hear about… until now.🎙️ Full, unfiltered conversation on the Drifting Cowboy Podcast.#vincegill #countrymusic #driftingcowboyvince gill, vince gill interview, how vince gill became famous, vince gill country music, country music podcast, drifting cowboy podcast, country music stories, vince gill career, country music history, nashville country music, classic country music, country music legends, behind the music country, country music interviews, rise to fame country music, how country stars make it, vince gill story, country music documentary, country music industry, country music storytelling

23 Apr 2026 - 1 h 24 min
episode Gary Stewart Was WILDER Than You Think… His Inner Circle Tells All artwork

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 with addiction, this is the side of Gary Stewart most people never got to see. This isn’t the polished version. This is the truth — straight from the people who lived it. If you think you know Gary Stewart… think again. Topics Covered: Gary Stewart’s personality off stage Wild road stories and pranks His struggles with addiction Behind-the-scenes moments from his career The real man behind the music Subscribe for more real stories from the legends and voices of country music. gary stewart, gary stewart stories, gary stewart podcast, drifting cowboy podcast, outlaw country, country music history, shannon stewart, boogie bob, terry porter, jimmy mcdonough, country music legends, classic country music, outlaw country music, country music documentary, gary stewart biography, country music stories, 70s country music, 80s country music, honky tonk music, country music interviews

16 Apr 2026 - 1 h 1 min
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