Drifting Cowboy

Drifting Cowboy

By Dillon Weldon

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 shap... more

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4.8

41 ratings


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Best of Drifting Cowboy

The most played episodes among Podcast App listeners.

  1. Number 1: What David Allan Coe Was Really Like | His Band Tells All

    David Allan Coe’s former band members sit down to tell the wild, uncensored stories from their years on the road with one of country music’s most legendary outlaws. They reveal what David was really like behind the scenes—the chaos, humor, music and unforgettable moments that never made it into the official story. Joining the conversation are renowned Nashville songwriters Gary Gentry, who wrote David Allan Coe’s classic hit “The Ride,” and Bobby Keel, who wrote “Time Off for Bad Behavior.” Together, they revisit the songs, characters and unbelievable road stories surrounding one of the most controversial and fascinating figures in outlaw country music. If you love David Allan Coe, classic country music, outlaw country and true stories told by the people who actually lived them, you don’t want to miss this episode of the Drifting Cowboy Podcast. Subscribe for more honest conversations with the artists, musicians and songwriters who built country music. David Allan Coe, David Allan Coe stories, David Allan Coe band, David Allan Coe documentary, David Allan Coe podcast, outlaw country, outlaw country music, classic country music, country music podcast, The Ride, The Ride David Allan Coe, Gary Gentry, Gary Gentry songwriter, Bobby Keel, Time Off for Bad Behavior, Nashville songwriters, country music stories, country music history, behind the music, road stories, Drifting Cowboy Podcast, Dillon Weldon

    1h 46min
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  2. Number 2: The REAL Story Behind “Long Black Train” | Josh Turner

    Josh Turner sits down with Dillon Weldon on the Drifting Cowboy Podcast to reveal the real story behind “Long Black Train”—including the powerful vision that inspired one of the most unforgettable songs in modern country music. Josh also reflects on 20 years of “Your Man” and shares the story behind the career-defining hit. He opens up about growing up surrounded by music, the vocal cord injury that left him wondering whether he would ever sing again, meeting the legendary Johnny Cash, and recording “Me and God” with bluegrass icon Ralph Stanley. From the songs that changed his life to the moments that nearly ended his career, Josh tells the stories behind his unmistakable voice, his faith, and his journey through country music. Subscribe to the Drifting Cowboy Podcast for honest conversations with the artists, songwriters, musicians, and legends who keep real country music alive. Josh Turner, Josh Turner interview, Josh Turner podcast, Long Black Train, Long Black Train story, story behind Long Black Train, Long Black Train meaning, Your Man Josh Turner, Your Man 20th anniversary, story behind Your Man, Josh Turner vocal cord injury, Josh Turner voice, Josh Turner Johnny Cash, Johnny Cash, Me and God, Ralph Stanley, Josh Turner songs, country music podcast, country music interviews, classic country music, real country music, Drifting Cowboy Podcast, Dillon Weldon

    47min
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  3. Number 3: 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

    54min
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  4. Number 4: What George Jones Was Really Like | Nancy Jones Tells All

    In this unforgettable episode of the Drifting Cowboy Podcast, Nancy Jones opens up about the real George Jones — the husband, the friend, and the man behind one of the greatest voices in country music history. Nancy shares deeply personal stories from their marriage, including the turbulent years, George’s battle with addiction, how she helped him get sober, and the life they built together away from the spotlight. Nancy also takes us inside George Jones’ friendships with fellow country music legends including Waylon Jennings, Johnny Cash, Johnny Paycheck, and others who were part of their lives during one of the most iconic eras in country music. She shares stories fans have never heard, memories from behind the scenes, the side of George the public rarely got to see, and the remarkable transformation that defined the final decades of his life. The conversation becomes especially emotional as Nancy reflects on George’s final days and shares the story of George Jones’ final words. More than a conversation about a country music legend, this is the story of the man Nancy knew, loved, fought for, and stood beside until the very end. If you grew up listening to George Jones, love classic country music, or have ever wondered what The Possum was really like when the stage lights went off, this is an episode you won’t want to miss. The Real George Jones | Stories Only Nancy Jones Could Tell George Jones, Nancy Jones, George Jones interview, Nancy Jones interview, George Jones widow, George Jones wife, The Real George Jones, George Jones stories, George Jones documentary, George Jones podcast, George Jones final words, George Jones death, George Jones sobriety, George Jones addiction, George Jones marriage, George Jones life story, George Jones biography, George Jones The Possum, The Possum, classic country music, country music history, country music legends, traditional country music, old country music, Waylon Jennings, Johnny Cash, Johnny Paycheck, Waylon Jennings stories, Johnny Cash stories, Johnny Paycheck stories, He Stopped Loving Her Today, George Jones He Stopped Loving Her Today, Grand Ole Opry, Nashville country music, country music podcast, Drifting Cowboy Podcast, Drifting Cowboy, country music interviews, country music stories, legendary country singers, outlaw country, real country music

    52min
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  5. Number 5: 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

    45min
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Drifting Cowboy episodes:

FAQs about Drifting Cowboy:

How many episodes does Drifting Cowboy have?

The podcast currently has 86 episodes available.

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