PODCAST · music
Drifting Cowboy
by Dillon Weldon
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.
Episodes
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Ricky Skaggs Reveals What Keith Whitley Was Really Like
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 country music—and his lifelong friendship with the late…
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What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay
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 incredible firsthand stories from decades of working with some of…
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Why Chet Atkins Fired Steve Wariner
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 shares what it was really like learning from one of the...
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Steve Wariner Blew Jerry Reed’s Mind in Front of Chet Atkins
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 Dottie West and Bob Luman, recording at Johnny Cash’s…
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The REAL Story Behind “Long Black Train” | Josh Turner
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 reflects on 20 years of “Your Man” and shares the story...
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What David Allan Coe Was Really Like | His Band Tells All
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, music and unforgettable moments that never made it into…
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What George Jones Was Really Like | Nancy Jones Tells All
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 stories from their marriage, including the turbulent…
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David Allan Coe's Lost Son Finally Speaks Out
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 him.David Allan Coe became one of the most controversial,...
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The Roger Miller Stories Only His Son Could Tell
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 of humor and unpredictable antics to the friendships,...
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Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories
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 Davis, for an episode packed with hilarious, unbelievable...
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Tanya Tucker’s Insane Rise to Stardom at Just 13 Years Old
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 “Delta Dawn” for the first time, and experiencing a rise to...
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The Bellamy Brothers Told Stories They Probably Shouldn’t Have
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 up in Florida, trying to survive before the hits, living…
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Chris Ledoux Was Country Music's Wildest Performer | Ned Ledoux
Ned LeDoux has new music on the way, including a brand-new music video coming soon — and in this episode, he joins Drifting Cowboy to talk about his own career, carrying on the LeDoux name, and the legacy of his father, Chris LeDoux. Ned shares what it was really like growing up on the road with...
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What Waylon Jennings Was Really Like | Whey Jennings
Whey Jennings joins the Drifting Cowboy Podcast for a conversation that goes far beyond country music. As the grandson of the legendary Waylon Jennings and Jessi Colter, Whey shares never-before-heard stories about growing up in one of country music's most iconic families, what Waylon was really...
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Daryle Singletary Stopped the Show Mid-Song | Jake Worthington
Jake Worthington joins the Drifting Cowboy Podcast to share stories from the road, his rise in country music, and the legends who helped shape his career. Jake talks about opening for Daryle Singletary, the unforgettable night Daryle stopped a show over a wrong note, lessons learned from Marty...
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Aaron Lewis Says Country Radio Blackballed Him
Aaron Lewis sits down for a raw conversation about his journey from the early days of Staind to becoming one of the most talked-about voices in country music. In this episode, Aaron opens up about how Staind began, what changed when he went from rock star to country artist, and why he believes...
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Is Traditional Country Music Finally Back? | Braxton Keith
Braxton Keith joins the Drifting Cowboy Podcast for a conversation about the resurgence of traditional country music, honky-tonks, songwriting, touring, and what it takes to build a fanbase in today's music industry. Braxton shares his thoughts on classic country influences, the current state of...
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Why Clint Black Walked Away
Country music legend Clint Black joins the Drifting Cowboy Podcast for one of his most revealing interviews yet. Clint opens up about his rise from Texas clubs to becoming the biggest debut in country music history, why he ultimately walked away from RCA Records, and the battles over creative...
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Kris Kristofferson Thought I was Johnny Cash | Paul Cauthen
Country artist and storyteller Paul Cauthen joins the Drifting Cowboy Podcast for one of the most emotional conversations yet. In this episode, Paul shares a heartbreaking story about Kris Kristofferson during his later years, including the moment Kris believed he was speaking to Johnny Cash.…
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The Night George Jones Shot at Peanutt Montgomery
George Jones shooting at Peanutt Montgomery sounds unbelievable—but this is the real story, told firsthand. In this episode of the Drifting Cowboy Podcast, legendary songwriter Peanutt Montgomery shares the night things went too far with George Jones, along with a lifetime of wild, unforgettable...
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Vince Gill Tells the REAL Story of His Rise
n this episode of the Drifting Cowboy Podcast, Vince Gill opens up about how he REALLY became a country star. From his early days chasing a dream to the moments that changed everything, Vince shares the truth behind his rise to fame in country music.This isn’t the polished version you’ve heard...
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Gary Stewart Was WILDER Than You Think… His Inner Circle Tells All
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…
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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…
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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”...
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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,...
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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...
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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...
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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…
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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…
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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...
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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...
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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,...
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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…
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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...
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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...
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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,...
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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...
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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...
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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…
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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...
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Jake Owen
Sign Up on Patreon for Exclusive Content: https://patreon.com/DillonWeldon?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_creator&utm_content=copyLinkJake Owen sits down with me for one of the most honest and wide-open conversations of his career. We talk Brooks & Dunn telling...
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Alex Miller
Patreon Clip: https://www.patreon.com/posts/alex-miller-x-142520479?utm_medium=clipboard_copy&utm_source=copyLink&utm_campaign=postshare_creator&utm_content=join_link From American Idol to sharing the stage with Hank Williams Jr., Tracy Byrd, and Emily Ann Roberts — country artist Alex Miller is...
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Blackberry Smoke's Charlie Starr
Blackberry Smoke’s Charlie Starr joins Drifting Cowboy for one of the wildest interviews yet. He opens up about recording with the legendary George Jones, life on the road, and the barroom brawl that left him bloodied with a broken beer bottle and a shard of glass in his head.From unforgettable...
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Craig Campbell
Country star Craig Campbell sits down with Drifting Cowboy for his most unfiltered interview yet. From exposing how Nashville’s big labels really operate, to opening up about his Grindstone Cowboy coffee shops (and the controversy it sparked with the writer of “Rhinestone Cowboy”), Craig doesn’t...
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Joe Nichols
Joe Nichols sits down for one of his most revealing interviews yet. In this episode of The Drifting Cowboy Podcast, Joe tells all—opening up about his struggles with addiction, why he once thought he wouldn’t live past 25, and how sobriety changed everything.But it’s not all heavy. Joe also…
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Marcus King
Marcus King sits down for an honest, unfiltered conversation about his struggles with addiction, his journey to sobriety, the influence of music in his life, and how love gave him a new sense of purpose. In this exclusive interview, Marcus opens up about the battles he’s faced, the artists who...
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Dusty Slay
Dusty Slay joins me for one of the funniest podcasts I’ve ever recorded. We go deep on country music, ask the burning question of what McDonald’s beef really is, trade insane stories, and I even get something off my chest. This episode is hilarious, raw, and guaranteed to make you laugh while…
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Shooter Jennings
Shooter Jennings joins the Drifting Cowboy Podcast for an unfiltered conversation about his father Waylon Jennings, the spirit of Outlaw Country, and the legacy that still shakes Nashville today. We dive into never-before-heard stories about Waylon and Jessi Colter, reflections on Johnny Cash…
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William Lee Golden of The Oak Ridge Boys
Step inside the life and legacy of William Lee Golden—the legendary Oak Ridge Boy with the iconic beard. In this exclusive conversation, we dive into untold stories of the Oak Ridge Boys, behind-the-scenes moments from country music history, the making of classic hits, and the family project…
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Ben and Noel Haggard
In this episode of Drifting Cowboy, I sit down with Ben and Noel Haggard—sons of the legendary Merle Haggard—for an unforgettable conversation filled with stories, laughs, and behind-the-scenes memories. We talk about their father’s legacy, growing up in the shadow of a country music giant, and...
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ABOUT THIS 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.
HOSTED BY
Dillon Weldon
CATEGORIES
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Frequently Asked Questions
How many episodes does Drifting Cowboy have?
Drifting Cowboy currently has 88 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Drifting Cowboy 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...
How often does Drifting Cowboy release new episodes?
Drifting Cowboy has 88 episodes. Check the episode list to see recent publication dates and frequency.
Where can I listen to Drifting Cowboy?
You can listen to Drifting Cowboy on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Drifting Cowboy?
Drifting Cowboy is created and hosted by Dillon Weldon.
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