Drifting Cowboy

Dillon Weldon
  • 4.8 (6)
  • 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. 24 MINS AGO

    Ronnie McDowell

    Ronnie McDowell has lived one of the most fascinating careers in country music history—and in this episode of Drifting Cowboy, he tells it like only he can. From the moment he released “The King Is Gone” as a tribute to Elvis Presley, Ronnie’s life changed forever. That song launched a career that would go on to include massive hits like “Older Women” and “Wondering Eyes,” along with decades of stories from inside the heart of country music. In this conversation, Ronnie opens up about his friendships and experiences with legends like Conway Twitty and George Jones—sharing stories you won’t hear anywhere else. He talks about the reality of fame, the highs and lows of the music business, and what it was really like being around some of the greatest artists of all time. But Ronnie’s story doesn’t stop with music. He’s also built an incredible second career as a painter, creating detailed portraits of icons like Elvis and other country legends. We dive into how that passion started, how serious he is about it, and why it means so much to him. This is one of those episodes that blends nostalgia, history, and raw storytelling—exactly what country music fans crave. If you love real stories about real country music, this one’s for you. ronnie mcdowell interview, the king is gone story, ronnie mcdowell elvis presley tribute, older women song meaning, wondering eyes song story, ronnie mcdowell conway twitty, ronnie mcdowell george jones stories, country music podcast, drifting cowboy podcast, country music legends interview, classic country stories, behind the songs country music, ronnie mcdowell paintings, elvis tribute artists, 80s country hits, nashville country music history, george jones stories, conway twitty stories, country music history podcast, classic country artists interview

    56 min

  2. MAR 19

    Hannah Dasher

    In this episode of Drifting Cowboy, I sit down with rising country artist and viral sensation Hannah Dasher to talk about her journey through country music—from grinding it out as a Nashville songwriter to breaking through as an artist and building a massive audience with her “Stand By Your Pan” cooking series. Hannah shares what it really takes to make it in today’s music industry, how she carved out her own lane, and the moments that changed everything for her career. Along the way, she tells incredible stories about country legends like Patsy Cline, Naomi Judd, and what it was like stepping into Loretta Lynn’s dresses. This is one of the most fun, honest, and story-filled conversations about country music you’ll hear—full of humor, insight, and a deep love for the history of the genre. hannah dasher, stand by your pan, hannah dasher interview, country music podcast, drifting cowboy podcast, nashville songwriter, female country artists, patsy cline story, naomi judd story, loretta lynn stories, country music history, viral country artists, tiktok country music, country music interviews, songwriting in nashville, how to make it in country music, classic country music, country music legends, nashville music scene, country music stories

    48 min

  3. MAR 12

    John Carter Cash

    John Carter Cash joins the Drifting Cowboy Podcast to share what his parents, Johnny Cash and June Carter Cash, were really like behind the scenes. As the only son of two of the most iconic figures in country music history, John Carter offers a rare and personal look at the lives, personalities, humor, struggles, and faith of the legendary couple. From growing up surrounded by music at the Cash home to witnessing his parents’ love story up close, this conversation reveals the human side of the Man in Black and the Carter Family icon that most fans never saw. In this episode, John Carter Cash talks about his childhood with Johnny and June, their relationship off stage, the influence of the Carter Family legacy, and the values his parents instilled in him. He also shares stories about life at the Cash household, what Johnny Cash was like as a father, how June Carter’s personality shaped their home, and what it was like growing up in one of the most famous families in American music. For country music fans, this is a rare opportunity to hear intimate stories and firsthand memories about two legends whose music changed the world. If you love classic country music, outlaw country, and the history behind the legends, this episode offers a fascinating glimpse into the private lives of Johnny Cash and June Carter Cash through the eyes of the person who knew them best. Johnny Cash, June Carter Cash, John Carter Cash, Johnny Cash interview, June Carter interview, Johnny Cash podcast, John Carter Cash interview, Johnny Cash family stories, Johnny Cash behind the scenes, June Carter Cash stories, Cash family history, Carter Family legacy, country music history, classic country music, outlaw country, Man in Black, Johnny Cash biography, June Carter biography, Cash family documentary, Johnny Cash son interview, country music legends, Nashville country music, country music podcast, Drifting Cowboy podcast, Dillon Weldon, country music storytelling, country music history podcast, Johnny Cash stories, June Carter Cash legacy

    59 min

  4. MAR 5

    Ben James | The Oak Ridge Boys

    The Oak Ridge Boys have one of the most legendary careers in country music history, but now the group has entered a brand-new chapter. In this episode of the Drifting Cowboy Podcast, Dillon Weldon sits down with Ben James, the newest member of the Oak Ridge Boys, to talk about how he joined the iconic group and what the future looks like.Ben shares the incredible story of how he became the new Oak Ridge Boy, what it’s like stepping into a legendary group with decades of history, and what fans can expect moving forward. We also talk about Ben’s musical background, the legacy of the Oak Ridge Boys, life on the road, and what it means to carry on one of country music’s most recognizable sounds.The Oak Ridge Boys have been a cornerstone of country music for generations, and this conversation gives fans a rare look inside the group as a new era begins.If you love classic country music, behind-the-scenes stories, and conversations with the legends and rising voices of the genre, subscribe to the channel for more interviews like this. Ben James, Oak Ridge Boys, new Oak Ridge Boy, Oak Ridge Boys new member, Oak Ridge Boys interview, Ben James interview, Drifting Cowboy Podcast, Dillon Weldon, country music podcast, Oak Ridge Boys history, William Lee Golden, Duane Allen, country music legends, country music interviews, classic country music, country music stories, country music podcast interview, Nashville country music, country music legends interview, country music history

    30 min

  5. FEB 26

    Jesse Keith Whitley

    There may be music from Keith Whitley that the world has never heard.In this powerful conversation, Jesse Keith Whitley opens up about his father’s legacy, the possibility of unreleased recordings, and what country fans have been wondering for decades.But this episode goes far beyond that.Jesse speaks candidly about growing up as the son of two country music icons, his relationship with Lorrie Morgan, his own journey through addiction and recent sobriety, and what it’s like carving out a career under one of the most legendary names in country music history. He also shares stories involving Sammy Kershaw, life on the road, finding his voice as an artist, and even the unexpected role cooking has played in his life.This is an honest, emotional, and revealing look at legacy, redemption, and the enduring impact of Keith Whitley on country music.If you’re a fan of classic country, outlaw stories, and untold music history, this is one you don’t want to miss! Keith Whitley unreleased music, unheard Keith Whitley songs, Jesse Keith Whitley interview, Keith Whitley lost recordings, Lorrie Morgan interview, country music podcast, classic country music stories, Sammy Kershaw story, country music legacy, Keith Whitley vault, outlaw country history, country music sobriety story, Jesse Keith Whitley sober, 90s country music, traditional country music, country music legends

    30 min

  6. FEB 20

    Rodney Crowell

    Rodney Crowell was there.Before the myth. Before the legend. Before the Outlaw era became a T-shirt.In this episode of Drifting Cowboy, Rodney Crowell reflects on his time inside one of the most influential circles in country music history — alongside Johnny Cash, Guy Clark, Townes Van Zandt, Jerry Jeff Walker, Rosanne Cash, and the writers who shaped an entire generation.From the raw reality of the Outlaw movement to the deeply human moments behind the music, Rodney shares what it was really like in the rooms where these songs — and these legends — were born. We talk about songwriting, loyalty, Nashville in its wildest years, and the difference between the public image and the private truth.This isn’t nostalgia. It’s perspective from someone who lived it.If you care about country music history, the outlaw era, and the real stories behind the icons, this conversation is one you won’t forget.Subscribe for more deep dives into the legends, the lore, and the untold stories of country music. country music podcast, Rodney Crowell interview, Johnny Cash stories, Guy Clark stories, Townes Van Zandt interview, outlaw country era, Nashville songwriting history, Rosanne Cash, Jerry Jeff Walker, classic country music, country music history, Drifting Cowboy podcast, legendary songwriters, behind the scenes country music, outlaw movement Nashville, 1970s country music, Texas songwriters, country music legends, storytelling in country music

    1h 10m

  7. FEB 12

    Rick Trevino

    Rick Trevino was one of the defining voices of 90s country music. With major radio hits, national tours, and a presence during one of country’s biggest boom periods, he lived the life many artists dream about. But at the height of the era, something shifted. In this episode of Drifting Cowboy, Rick Trevino reflects on the rise of 90s country, the pressure of fame, navigating Nashville as a bilingual/Latino artist, and the pull that brought him back to his roots. He opens up about identity, industry expectations, touring during the golden era of country radio, and what it really felt like behind the spotlight. This is a thoughtful look at one of country music’s most transformative decades — and the personal crossroads that changed everything. If you love 90s country, classic Nashville stories, and honest conversations about fame, culture, and legacy, this one is for you. Subscribe for more in-depth country music interviews and untold stories from the artists who shaped the genre. rick trevino, rick trevino interview, 90s country music, 1990s country, latino country artist, bilingual country singer, nashville country music, drifiting cowboy podcast, country music podcast, country music history, los super seven, 90s country radio, 90s country stars, country music fame, country music industry, classic country interviews, country music legends, texas country music, hispanic country music, country music storytelling

    59 min

  8. FEB 5

    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
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4.8
out of 5
6 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
    67
  • Rating
    Explicit
  • Copyright
    © Dillon Weldon
  • Show Website
    Drifting Cowboy

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