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Drifting Cowboy

by Dillon Weldon
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Latest episodes

  • Ricky Skaggs Reveals What Keith Whitley Was Really Like

    October 20, 2026 · 1 hr 8 min

    Country music legend and 15-time GRAMMY Award winner Ricky Skaggs joins the Drifting Cowboy Podcast for an unforgettable conversation about his extraordinary journey from a young Kentucky bluegrass prodigy to one of the biggest stars in…

  • What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay

    October 15, 2026 · 1 hr 10 min

    What were Conway Twitty and Loretta Lynn REALLY like behind the scenes? In this episode of the Drifting Cowboy Podcast, legendary country music booking agent Jimmy Jay joins us alongside his sons, Jerry Jay and Jeff Jay, to share…

  • Why Chet Atkins Fired Steve Wariner

    October 1, 2026 · 1 hr 9 min

    Here is part two of Steve Wariner's Drifting Cowboy episode where he tells the hilarious story of Chet Atkins "firing" him after Steve scored a big hit. Steve explains how his success as a solo artist changed his role in Chet’s band, and…

  • Steve Wariner Blew Jerry Reed’s Mind in Front of Chet Atkins

    September 24, 2026 · 1 hr 2 min

    Hey Drifters!In Part 1 of this Drifting Cowboy conversation, Steve Wariner takes us back to the very beginning of his career and the unbelievable run of people who helped shape him before the hits ever came.Steve talks about playing with…

  • The REAL Story Behind “Long Black Train” | Josh Turner

    September 10, 2026 · 47 min

    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…

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  • What David Allan Coe Was Really Like | His Band Tells All

    September 3, 2026 · 1 hr 46 min

    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…

  • What George Jones Was Really Like | Nancy Jones Tells All

    August 20, 2026 · 51 min

    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…

  • David Allan Coe's Lost Son Finally Speaks Out

    August 13, 2026 · 1 hr 23 min

    For the first time on Drifting Cowboy, David Allan Coe’s son shares the deeply personal and heartbreaking story of growing up without a relationship with his famous father and spending years hoping for the chance to finally connect with…

  • The Roger Miller Stories Only His Son Could Tell

    August 6, 2026 · 46 min

    Dean Miller, son of country music legend Roger Miller, joins the Drifting Cowboy Podcast to share the stories only a son could tell. Dean opens up about what Roger Miller was really like away from the spotlight—from his unforgettable sense…

  • Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories

    July 30, 2026 · 56 min

    Johnny Cash once showed up at the Statler Brothers’ house and made biscuits—and somehow, that’s only the beginning. Wilson Fairchild, the sons of Statler Brothers legends Don and Harold Reid, join me alongside the next generation, Jack and…

  • Tanya Tucker’s Insane Rise to Stardom at Just 13 Years Old

    July 16, 2026 · 1 hr 8 min

    Tanya Tucker joins the Drifting Cowboy Podcast to tell the incredible story of how she became a superstar at just 13 years old. Tanya takes us back to the beginning of her career, signing with legendary producer Billy Sherrill, hearing…

  • The Bellamy Brothers Told Stories They Probably Shouldn’t Have

    July 9, 2026 · 35 min

    In this episode of Drifting Cowboy, Dillon Weldon sits down with The Bellamy Brothers for one of the wildest conversations yet. Howard and David Bellamy tell unbelievable stories from before and after country music fame, including growing…

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About the show

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.