Drifting Cowboy

What was Gary Stewart REALLY like when the spotlight turned off?
In this episode of Drifting Cowboy, we sit down with the people who knew him best — his daughter Shannon Stewart, longtime guitarist Boogie Bob, bodyguard Terry Porter, and acclaimed biographer Jimmy McDonough — for an unfiltered look at one of country music’s most misunderstood legends.
They share never-before-heard stories about Gary’s wild lifestyle, his struggles, his sense of humor, and the moments that defined him behind the scenes. From chaotic nights on the road to unforgettable pranks and the reality of his battles with addiction, this is the side of Gary Stewart most people never got to see.
This isn’t the polished version. This is the truth — straight from the people who lived it.
If you think you know Gary Stewart… think again.
Topics Covered:
Gary Stewart’s personality off stage
Wild road stories and pranks
His struggles with addiction
Behind-the-scenes moments from his career
The real man behind the music
Subscribe for more real stories from the legends and voices of country music.
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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.

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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.
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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.
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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.

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