Drifting Cowboy

Dillon Weldon
  • 4.9 (70)
  • Music Interviews
  • Updated Weekly

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.

  1. 1d ago

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

    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 mechanical bulls and pyrotechnics on stage to the wild energy of those legendary concerts. He also opens up about finishing some of his dad’s unfinished songs, building his own path in country music, and working with Mac McAnally to help bring those songs to life. Ned also talks about Chris LeDoux’s friendship with Garth Brooks, the impact Garth had on introducing Chris to a wider country audience, and why Chris LeDoux remains one of the most beloved and authentic figures in country music history. This is a conversation about family, rodeo, country music, legacy, and the kind of performer they simply don’t make anymore. Subscribe for more long-form conversations with country music legends, songwriters, and the people who lived the stories behind the songs. #NedLeDoux #ChrisLeDoux #CountryMusic Ned LeDoux, Chris LeDoux, Chris LeDoux interview, Ned LeDoux interview, Ned LeDoux music video, new Ned LeDoux music, Chris LeDoux stories, Chris LeDoux concerts, Chris LeDoux live, Chris LeDoux mechanical bull, Chris LeDoux pyrotechnics, Chris LeDoux rodeo, 1976 bareback champion, rodeo country music, country music podcast, Drifting Cowboy, country music interviews, classic country, real country music, Garth Brooks Chris LeDoux, Chris LeDoux Garth Brooks friendship, Mac McAnally, Ned LeDoux songs, finishing Chris LeDoux songs, Chris LeDoux legacy, western music, cowboy country music, country music legends, untold country music stories, country music history, rodeo champion singer, Chris LeDoux band, life on the road country music

    43 min

  2. Jun 18

    What Waylon Jennings Was Really Like | Whey Jennings

    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 career on his own terms. From family stories and outlaw country history to redemption, faith, and second chances, this is one of the most honest conversations we've had on the podcast. If you're a fan of Waylon Jennings, outlaw country, classic country music, or powerful comeback stories, this episode is for you. #WaylonJennings #WheyJennings #OutlawCountry #CountryMusic #DriftingCowboyPodcast Waylon Jennings, Whey Jennings, Jessi Colter, outlaw country, country music podcast, Waylon Jennings stories, what Waylon Jennings was really like, Whey Jennings interview, Waylon Jennings grandson, country music history, classic country music, outlaw movement, Nashville podcast, country singer interview, sobriety story, addiction recovery, getting sober, redemption story, country music legends, Drifting Cowboy Podcast, Jesse Keith Whitley, Johnny Cash, Willie Nelson, Hank Williams Jr, Merle Haggard, country music conversation, behind the music, country music documentary, country music fans, outlaw country music

    45 min

  3. Jun 11

    Daryle Singletary Stopped the Show Mid-Song | Jake Worthington

    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 future, this is one of the most entertaining Jake Worthington interviews you'll hear.If you enjoy stories about classic country music, Daryle Singletary, George Jones, Merle Haggard, Marty Stuart, Miranda Lambert, and the artists keeping traditional country alive, be sure to like, subscribe, and share the episode.#JakeWorthington #DaryleSingletary #CountryMusic #DriftingCowboyPodcastJake Worthington, Daryle Singletary, Jake Worthington interview, Daryle Singletary story, country music podcast, traditional country music, Marty Stuart, Miranda Lambert, The Voice, classic country, outlaw country, Texas country, country singer podcast, George Jones, Merle Haggard, Randy Travis, Alan Jackson, Nashville, country music stories, country music legends, Drifting Cowboy Podcast, Dillon Weldon, country music interview, country music history, neotraditional country, Grand Ole Opry, country music fans, country music conversation, country music documentary, country music storytelling, western music, honky tonk music, country music culture, classic country stories, Jake Worthington podcast, Daryle Singletary interview, traditional country singer, country music YouTube, country music fans podcast, Nashville podcast, country music legends stories, country music entertainment, old school country music, country music discussion, country music community, country music heritage, Texas honky tonk, country music industry, country music history podcast

    54 min

  4. May 29

    Is Traditional Country Music Finally Back? | Braxton Keith

    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, Cody Johnson, and classic country music, this is an episode you won't want to miss.🔔 Subscribe for more conversations with country music legends, rising stars, songwriters, and the people who shaped country music history.Follow Drifting Cowboy:[Insert Links]Follow Braxton Keith:[Insert Links]#CountryMusic #BraxtonKeith #TraditionalCountryBraxton Keith, Braxton Keith podcast, Braxton Keith interview, traditional country music, country music podcast, Drifting Cowboy Podcast, country music history, honky tonk music, Texas country music, neo traditional country, traditional country comeback, country music 2026, George Strait, Alan Jackson, Randy Travis, Zach Top, Cody Johnson, classic country music, outlaw country, country singer interview, Nashville, Texas country, country music fans, country music conversation, country music legends, rising country stars, real country music, country music industry, western music, honky tonks, country artists, country music stories, country music culture, country music community, new country music, independent country music, country music discussion, country music podcast interview, country music revival, country music comeback, Drifting Cowboy, Dillon Weldon, Braxton Keith country music, traditional country revival, modern country music, country music trends, country music influencers, country lifestyle, country western music, classic country sound, authentic country music, country music fans podcast, Braxton Keith 2026, country music interview podcast

    48 min

  5. May 21

    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

    44 min

  6. May 15

    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

    31 min

  7. Apr 30

    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

    58 min

  8. Apr 23

    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

    1h 24m
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4.9
out of 5
70 Ratings

About

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.

Information

  • Creator
    Dillon Weldon
  • Years Active
    2025 - 2026
  • Episodes
    76
  • Rating
    Explicit
  • Copyright
    © Dillon Weldon
  • Show Website
    Drifting Cowboy

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