Drifting Cowboy

Dillon Weldon
  • 4.8 (43)
  • 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. 2D AGO

    Georgette Jones

    In this powerful and intimate conversation, Georgette Jones opens up about what life was really like growing up as the daughter of two country music legends—George Jones and Tammy Wynette. Beyond the headlines, hit songs, and public struggles, Georgette shares personal stories, family memories, and behind-the-scenes moments that reveal who George and Tammy truly were when the lights were off and the world wasn’t watching.From childhood memories inside one of country music’s most famous families to honest reflections on love, fame, and legacy, this episode offers a rare, human look at two icons whose lives were as complicated as their music was timeless. This is not the tabloid version—it’s the truth, told by the person who lived it.If you care about country music history, real storytelling, and the people behind the legends, this is a conversation you don’t want to miss.George Jones, Tammy Wynette, Georgette Jones, George and Tammy, George Jones documentary, Tammy Wynette documentary, country music history, classic country music, outlaw country, country music legends, George Jones stories, Tammy Wynette stories, behind the music, country music podcast, Drifting Cowboy podcast, Nashville country music, real country stories, music legacy, country music family, country music interviews, classic country icons

    55 min

  2. 12/24/2025

    Ray Benson

    Ray Benson of Asleep at the Wheel joins Drifting Cowboy for a deep-cut conversation about the people and moments that shaped country music history. Ray shares rare stories about his close friendships with Willie Nelson and Merle Haggard, including the time he watched Merle cuss out his label head Rick Blackburn. He talks about living in the same neighborhood as Townes Van Zandt and Blaze Foley, crossing paths with Stevie Ray Vaughan and Jimmie Vaughan before superstardom, and how Naomi Judd got the name Wynonna from Asleep at the Wheel—then legally renamed her daughter at 14 years old. This episode dives into outlaw country, Texas music, Americana, the Austin scene, Nashville politics, songwriting culture, and the unfiltered truth behind the legends. If you care about real country music stories, this is one you don’t skip.Willie Nelson podcast, Merle Haggard stories, Ray Benson interview, Asleep at the Wheel podcast, Townes Van Zandt stories, Blaze Foley stories, Stevie Ray Vaughan interview, Jimmie Vaughan stories, Naomi Judd Wynonna name origin, outlaw country history, Texas country music, Americana podcast, country music storytelling

    1 hr

  3. 12/18/2025

    Ward Davis

    Country songwriter Ward Davis joins Drifting Cowboy for a raw, no-filter conversation about his path through modern outlaw country — including the unbelievable moment Willie Nelson and Merle Haggard both recorded his song “Unfair Weather Friend.”Ward tells the full story behind how that song came together, what it meant to have two all-time legends cut the same song, and how that moment reshaped his career. He also talks about his longtime friendship with Cody Jinks, recording with Clint Black, and navigating success outside the Nashville system.Along the way, Ward shares a powerful story about meeting Kris Kristofferson and performing a show with him, offering rare insight into one of country music’s most respected icons.This episode is about songwriting, grit, loyalty, and the quiet moments that define a career — the parts most people never hear.If you care about real country music, the writers behind the songs, and the stories that live off the radio dial, this episode is for you.🎙️ Drifting Cowboy PodcastHosted by Dillon WeldonNew episodes featuring legendary artists, songwriters, and untold stories from country music history.Ward Davis, Ward Davis podcast, Ward Davis interview, Willie Nelson, Merle Haggard, Willie Nelson Merle Haggard song, Unfair Weather Friend, Kris Kristofferson, Ward Davis Kris Kristofferson, Cody Jinks, Ward Davis Cody Jinks, Clint Black, outlaw country, modern outlaw country, country songwriting, songwriter podcast, country music podcast, behind the songs country music, Texas country music, independent country artists, Drifting Cowboy podcast, Dillon Weldon, country music history, Nashville songwriting

    51 min

  4. 12/11/2025

    Jeannie C. Riley

    Country music icon Jeannie C. Riley sits down for a rare, wide-open conversation about her life, her career, and the stories behind “Harper Valley PTA.” She shares unforgettable moments with Tom T. Hall, Charlie Daniels, and other Nashville legends, while reflecting on the highs, the heartbreak, and what she really lived through in the industry.This is Jeannie C. Riley like you’ve never seen her — honest, sharp, funny, and full of wisdom from a lifetime in country music. If you love classic country, storytelling, or behind-the-scenes history, this two-hour interview is a treasure.jeannie c riley, jeannie c riley interview, harper valley pta, tom t hall, charlie daniels, drifting cowboy podcast, country music history, classic country stories, harper valley pta story, jeannie c riley podcast, nashville legends, 60s country music, female country artists, country music interviews, jeannie c riley untold story, harper valley pta songwriter, tom t hall stories, charlie daniels stories, country music women, jeannie c riley 2025

    1h 58m

  5. 12/04/2025

    Whisperin’ Bill Anderson

    Whisperin’ Bill Anderson joins The Drifting Cowboy Podcast for a deep dive into one of the most legendary careers in country music history. From writing timeless songs like Whiskey Lullaby and Give It Away to sharing the stage with icons like Roger Miller and Faron Young, Bill opens up about the stories, struggles, and moments that shaped a lifetime of hits. He also talks about hosting Country Family Reunion, his early days on television game shows and soap operas, and what it truly means to stay relevant in country music for over six decades. 🎧 Full of laughter, wisdom, and never-before-told stories from a Hall of Fame songwriter. 👉 Watch the full interview and subscribe for more conversations with the legends who built country music. Bill Anderson, Whisperin Bill Anderson, Roger Miller, Faron Young, Whiskey Lullaby, Give It Away, Country Family Reunion, Grand Ole Opry, Country Music Hall of Fame, Nashville, Country Music History, Country Legends, Songwriting, Country Songwriter Stories, Drifting Cowboy Podcast, Dillon Weldon, Country Interviews, Behind the Songs, Country Music Icons, Country Music Stories, Traditional Country, 90s Country, Classic Country, Bill Anderson Interview, Bill Anderson Podcast, Country Storytellers, Country Music Hall of Famer

    35 min

  6. 11/27/2025

    Bernie Leadon (Founding Member of The Eagles)

    Founding Eagles member Bernie Leadon joins me to share the real story behind one of the most important chapters in American music. Bernie talks about his early years with Gram Parsons and the Flying Burrito Brothers, his memories from Altamont Speedway, and the musical and personal moments that shaped the rise of The Eagles. We dive deep into writing classics like “Witchy Woman,” the band’s early chemistry, why he left, and what it was like returning decades later for the History of the Eagles tour. Bernie also opens up about Gram’s death, the California country-rock scene, and the new music he’s creating today. If you love the Eagles, Gram Parsons, real music history, or the roots of country rock, this episode is packed with stories you won’t hear anywhere else.bernie leadon, eagles founding member, the eagles, gram parsons, flying burrito brothers, altamont speedway, witchy woman, eagles interview, gram parsons stories, bernie leadon interview, drifting cowboy podcast, dillon weldon, country rock history, classic rock stories, music history podcast, history of the eagles, california country rock, american music history, gram parsons death, eagles founding story, bernie leadon new music, eagles documentary, country music podcast, rock and roll history

    53 min

  7. 11/20/2025

    Mickey Raphael

    Legendary harmonica player Mickey Raphael joins me for a deep dive into life on the road with Willie Nelson — including an unbelievable story about the night Willie’s crew ended up getting a ride to a show from the Hells Angels. Mickey also talks about working with iconic songwriters like Guy Clark and Townes Van Zandt, his memories from decades of touring, his solo projects, and the exciting new music he’s working on now. This episode is a front-row seat to country music history from a man who lived it, breathed it, and shaped it beside one of the greatest of all time.mickey raphael, willie nelson, hells angels, hells angels story, mickey raphael interview, willie nelson band, guy clark, townes van zandt, outlaw country stories, country music podcast, drifting cowboy podcast, harmonica player, willie nelson road stories, country music legends, country music history, nashville podcast, dillon weldon, country music interview, willie nelson stories, mickey raphael harmonica, country road stories

    41 min

  8. 11/13/2025

    Waylon Jennings' Band The Waylors

    Join Patreon for Exclusive Content:https://patreon.com/DillonWeldon?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_creator&utm_content=copyLinkStep inside the world of Waylon Jennings like you’ve never heard it before. In this episode, the legendary members of Waylon’s band sit down and tell ALL — the untold, unbelievable, and downright wild stories from life on the road with the Outlaw himself.They share what it was really like working for Waylon, the pranks they pulled on him, how Big Bird actually caught on fire, behind-the-scenes moments from The Dukes of Hazzard, and memories of Buddy Holly and The Crickets, Nashville in the ’60s and ’70s, and the rise of the Outlaw movement.This episode is pure country music history straight from the men who lived it. If you love Waylon Jennings, classic country, or behind-the-scenes stories that feel like opening a hidden vault, this is one you won’t forget.waylon jennings, waylon jennings interview, waylon jennings band, outlaw country, outlaw country stories, buddy holly stories, dukes of hazzard, country music history, waylon jennings podcast, waylon jennings documentary, waymore’s blues band, dillon weldon drifting cowboy, big bird on fire story, classic country stories, nashville history, country music legends, untold outlaw stories, jennings family, honky tonk history, waylon jennings 2025, drifting cowboy podcast

    1h 25m
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4.8
out of 5
43 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
    57
  • Rating
    Explicit
  • Copyright
    © Dillon Weldon
  • Show Website
    Drifting Cowboy

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