Drifting Cowboy

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 b...

15 Jan 1h 4min

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 ...

1 Jan 54min

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 ...

24 Dec 202559min

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 b...

18 Dec 202550min

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. Ha...

11 Dec 20251h 57min

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...

4 Dec 202535min

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 B...

27 Nov 202553min

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...

20 Nov 202540min