Drifting Cowboy

Dillon Weldon
  • 4.8 (5)
  • 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. 6D AGO

    Bobby Bare

    Bobby Bare doesn’t just remember country music history — he helped shape it.In this rare, in-depth interview, Bobby Bare reflects on a career that places him at the center of country music’s most important moments. From his role in the early creative culture that helped influence the Fender Stratocaster, to discovering and supporting artists like Waylon Jennings and Billy Joe Shaver, to firsthand stories involving Johnny Cash, Tom T. Hall, and Chet Atkins, this conversation captures living history from one of the genre’s most influential figures.Bobby shares stories you don’t hear in documentaries or highlight reels — the behind-the-scenes moments, the creative risks, the personalities, and the decisions that quietly changed the course of country music. This isn’t a highlight package or a greatest-hits recap. It’s a firsthand account from someone who was there when modern country music was taking shape.If you care about country music’s roots, the people behind the legends, and how the genre truly evolved, this is a conversation worth preserving.Subscribe for more long-form interviews and deep dives into country music history, storytelling, and legacy.bobby bare, bobby bare interview, country music history, rare country music interview, waylon jennings, johnny cash, tom t hall, chet atkins, billy joe shaver, classic country music, outlaw country, nashville music history, music row nashville, country music legends, country music documentary, fender stratocaster history, guitar history, drifting cowboy podcast, country music podcast, classic country stories

    1h 11m

  2. JAN 22

    John Ford Coley

    Most people know Dan Seals as a country music legend — but before the hits on country radio, he was England Dan, one half of the massively successful duo England Dan & John Ford Coley. In this episode of the Drifting Cowboy Podcast, John Ford Coley sits down with me to tell the real story behind his partnership with Dan Seals, the rise of England Dan & John Ford Coley, and the honest, human reasons the duo ultimately broke up. John opens up about Dan’s transition into country music stardom, life after the split, and what it was really like navigating success at the height of the 1970s music industry. John also shares incredible firsthand stories from touring with Elton John, opening for Led Zeppelin, sharing stages with Three Dog Night, and how his career unexpectedly shifted into acting after the duo came to an end. This isn’t gossip or revisionist history — it’s reflection, perspective, and music history told by the man who lived it. If you’ve ever wondered why Dan Seals walked away from England Dan, or how one of the biggest soft-rock duos of the 1970s came to an end, this conversation finally fills in the blanks. Dan Seals, England Dan, John Ford Coley, England Dan and John Ford Coley, Dan Seals country music, Dan Seals England Dan, why Dan Seals left England Dan, Dan Seals breakup, John Ford Coley interview, Dan Seals story, country music history, classic country music, 70s soft rock, yacht rock stories, Elton John tour stories, Led Zeppelin opening act, Three Dog Night tour, country music podcast, music history podcast, Drifting Cowboy Podcast, country music interviews, classic hits behind the scenes, music legends interview, Dan Seals legacy

    36 min

  3. JAN 15

    Gary Gentry

    What really inspired “The Ride” — one of the most haunting songs in country music history?Songwriter Gary Gentry (“The Ride,” “The One I Loved Back Then,” and more) tells the unbelievable true story behind the song that has puzzled and fascinated fans for decades. After a night of heavy drinking, drugs, and reckless curiosity, Gary and a group of friends held a seance to provoke the spirit of Hank Williams.What happened next would stay with Gary forever.In this podcast, Gary recounts seeing what he believes was Hank Williams’ ghost — an encounter that later shaped the writing of “The Ride,” a song that feels less like fiction and more like a message passed down from country music’s past.This is not a rumor.This is not a legend told secondhand.This is the story straight from the songwriter himself.If you love:• Country music history• Nashville songwriting stories• Hank Williams folklore• Dark, strange, and unforgettable moments in music…this conversation is for you.Gary Gentry, The Ride song, Hank Williams ghost, Hank Williams seance, The Ride Gary Gentry, country music folklore, songwriting stories, Nashville songwriter, paranormal country music, haunted country music, Hank Williams legend, outlaw country history, The One I Loved Back Then, David Allan Coe songwriter, country music podcast, Drifting Cowboy podcast, strange country music stories, music history podcast, Hank Williams mystery, supernatural songwriting

    1h 5m

  4. JAN 1

    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

  5. 2025-12-24

    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

  6. 2025-12-18

    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

  7. 2025-12-11

    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

  8. 2025-12-04

    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
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4.8
out of 5
5 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
    60
  • Rating
    Explicit
  • Copyright
    © Dillon Weldon
  • Show Website
    Drifting Cowboy

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