Drifting Cowboy
by Dillon Weldon
Latest episode
Ricky Skaggs Reveals What Keith Whitley Was Really Like
Ricky Skaggs Reveals What Keith Whitley Was Really Like
About this podcast
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
The newest 20 of 89 episodes
- Ricky Skaggs Reveals What Keith Whitley Was Really Like · 1 h 7 minCountry 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…
- What Conway Twitty & Loretta Lynn Were REALLY Like | Jimmy Jay · 1 h 10 minWhat 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…
- Why Chet Atkins Fired Steve Wariner · 1 h 8 minHere 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…
- Steve Wariner Blew Jerry Reed’s Mind in Front of Chet Atkins · 1 h 1 minHey 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…
- The REAL Story Behind “Long Black Train” | Josh Turner · 47 minJosh 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…
- What David Allan Coe Was Really Like | His Band Tells All · 1 h 45 minDavid 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 George Jones Was Really Like | Nancy Jones Tells All · 51 minIn 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…
- David Allan Coe's Lost Son Finally Speaks Out · 1 h 23 minFor 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…
- The Roger Miller Stories Only His Son Could Tell · 46 minDean 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…
- Johnny Cash Made Biscuits at Our House | Wild Statler Brothers Stories · 56 minJohnny 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…
- Tanya Tucker’s Insane Rise to Stardom at Just 13 Years Old · 1 h 7 minTanya 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…
- The Bellamy Brothers Told Stories They Probably Shouldn’t Have · 35 minIn 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…
- Chris Ledoux Was Country Music's Wildest Performer | Ned Ledoux · 43 minNed 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…
- What Waylon Jennings Was Really Like | Whey Jennings · 45 minWhey 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…
- Daryle Singletary Stopped the Show Mid-Song | Jake Worthington · 54 minJake 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…
- Aaron Lewis Says Country Radio Blackballed Him · 23 minAaron 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…
- Is Traditional Country Music Finally Back? | Braxton Keith · 48 minBraxton 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…
- Why Clint Black Walked Away · 44 minCountry 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…
- Kris Kristofferson Thought I was Johnny Cash | Paul Cauthen · 31 minCountry 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…
- The Night George Jones Shot at Peanutt Montgomery · 58 minGeorge 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…
