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Drifting Cowboy: Daily Summaries Delivered
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.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 2 weeks ago1h 7m
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 Keith Whitley.Ricky takes us all the way back to his childhood, when his father bought him his first mandolin for just $5 at the age of five. By six, he was sharing the stage with the Father of Bluegrass, Bill Monroe. At just seven years old, he appeared on television with Lester Flatt and Earl Scruggs on the Martha White Flour Hour, performing the bluegrass classic "Ruby."Ricky also opens up about one of the most important relationships of his life: his friendship with Keith Whitley. Long before either became a country music star, the two young musicians were playing bluegrass together. Ricky shares personal memories of Keith's personality, their early adventures, their years performing with Ralph Stanley and the heartbreaking moment he learned of Keith Whitley's death in 1989.From his early days with Ralph Stanley and the Clinch Mountain Boys to his rise as a country music superstar, Ricky reflects on the people, experiences and unexpected twists of fate that shaped his career.He even reveals the remarkable story of how a chance upgrade to first class on an airplane led to a meeting that helped him land his record deal.In this episode, Ricky Skaggs discusses:Growing up in Kentucky and receiving his first $5 mandolin at age fivePlaying onstage with bluegrass pioneer Bill Monroe at just six years oldPerforming "Ruby" with Flatt and Scruggs on the Martha White Flour Hour at age sevenMeeting Keith Whitley and the beginning of their lifelong friendshipWhat Keith Whitley was really like away from the spotlightPlaying bluegrass with Keith Whitley and Ralph StanleyThe heartbreaking news of Keith Whitley's deathHis journey from bluegrass prodigy to country music superstarThe unbelievable first-class airplane encounter that helped launch his recording careerAnd much more!Few artists have witnessed as much country and bluegrass music history firsthand as Ricky Skaggs. From Bill Monroe and Ralph Stanley to Keith Whitley and the golden era of traditional country music, Ricky shares stories that only someone who lived them could tell.Join us for an intimate look at the life, music, friendships and legacy of one of country music's most influential artists.Subscribe to the Drifting Cowboy Podcast for more in-depth conversations with legendary country music artists, songwriters and the people who helped make country music history.#RickySkaggs #KeithWhitley #CountryMusic #BluegrassMusic #DriftingCowboy
- 2 weeks ago1h 10m
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 the biggest names in country music history.Jimmy Jay spent years representing country music icons Conway Twitty and Loretta Lynn, getting a rare behind-the-scenes look at their lives, personalities, and careers. Now, he and his sons are pulling back the curtain on what it was really like working with these two country music legends.But the stories don't stop with Conway and Loretta.The Jay family shares unforgettable memories involving Jerry Lee Lewis, Roy Orbison, Del Reeves, Randy Travis, George Jones, and Merle Haggard. From George Jones and Merle Haggard failing to show up for performances to the unpredictable personalities of country music's biggest stars, this conversation offers a fascinating look at the golden age of country music.We also dive deep into the business side of the music industry, exploring what it took to operate an independent booking agency, negotiate with promoters, book major country music acts, and survive in the wild world of the entertainment business before the internet changed everything.These aren't stories from history books. They're firsthand accounts from a family that spent decades working behind the scenes with some of the greatest entertainers who ever lived.If you love classic country music, the untold stories of Nashville, and legends like Conway Twitty, Loretta Lynn, George Jones, Merle Haggard, Waylon Jennings, and Johnny Cash, this is a conversation you won't want to miss.Subscribe to the Drifting Cowboy Podcast for more exclusive interviews, untold stories, and conversations with the legends who made country music history.#ConwayTwitty #LorettaLynn #ClassicCountryMusic #CountryMusicHistory #DriftingCowboy
- Oct 1, 20261h 8m
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 greatest musicians and producers in country music history.Steve also opens up about his friendship with Jerry Reed later in Jerry’s life, sharing stories and memories of the legendary guitarist, entertainer, and songwriter. He talks about working with acclaimed producer Tony Brown, the people who helped shape his career, and the relationships he built throughout decades in Nashville.We also get into the story behind one of Steve Wariner’s most powerful songs, “Holes in the Floor of Heaven,” including the inspiration and songwriting process behind the country classic. From Chet Atkins and Jerry Reed to hit records, songwriting, Nashville history, and life on the road, this episode is packed with stories from a career that has touched multiple generations of country music.If you love real country music, legendary Nashville stories, classic country songwriting, and hearing the history straight from the people who lived it, make sure you subscribe to Drifting Cowboy and check out part one of our conversation with Steve Wariner.Steve Wariner, Steve Wariner interview, Steve Wariner podcast, Drifting Cowboy, Drifting Cowboy podcast, Chet Atkins, Chet Atkins Steve Wariner, Steve Wariner Chet Atkins, Jerry Reed, Steve Wariner Jerry Reed, Tony Brown, Steve Wariner Tony Brown, Holes in the Floor of Heaven, Holes in the Floor of Heaven story, Holes in the Floor of Heaven Steve Wariner, country music podcast, country music interview, classic country music, real country music, traditional country music, Nashville stories, Nashville history, country music history, country music legends, legendary country singers, country music songwriting, Nashville songwriter, Steve Wariner songs, Steve Wariner hits, Chet Atkins stories, Jerry Reed stories, Nashville musicians, country guitar, country music documentary, country music stories
- Sep 24, 20261h 1m
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 studio with Johnny Cash producing, and what it was like meeting Cash for the first time. He also tells the incredible story of meeting Chet Atkins at RCA while Jerry Reed was in the room — including the moment Steve played “I’m Already Taken” and Jerry looked at Chet and said, “Damn, Chet, sign this boy. What do you want, blood?!”Steve opens up about learning from some of the greatest artists and musicians in country music history, finding his own sound, and the events that eventually put him on the path toward becoming one of Nashville’s most respected singers, songwriters, and guitar players.This episode ends right as Steve Wariner’s solo career begins to take off. Part 2 is coming soon, where we’ll continue the story through the next chapter of his career.If you love classic country music, Nashville history, Johnny Cash stories, Chet Atkins, Jerry Reed, Dottie West, Bob Luman, and the stories behind the artists who built country music, this is one you don’t want to miss.Subscribe to Drifting Cowboy for more long-form conversations with the legends, songwriters, musicians, and characters who made country music what it is.Steve Wariner, Steve Wariner interview, Steve Wariner podcast, Steve Wariner Chet Atkins, Steve Wariner Jerry Reed, Steve Wariner Johnny Cash, Steve Wariner Dottie West, Steve Wariner Bob Luman, Chet Atkins, Chet Atkins interview, Jerry Reed, Jerry Reed stories, Johnny Cash, Johnny Cash stories, Johnny Cash studio, Dottie West, Bob Luman, I'm Already Taken, Steve Wariner I'm Already Taken, classic country music, country music history, country music legends, Nashville history, Nashville music history, Grand Ole Opry, RCA Nashville, country music podcast, classic country podcast, Drifting Cowboy, Drifting Cowboy podcast, country music interviews, country singer interviews, country guitar players, Nashville session musicians, country music stories, traditional country music, 1970s country music, 1980s country music, country music documentary
- Sep 10, 202646 min
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 behind the career-defining hit. He opens up about growing up surrounded by music, the vocal cord injury that left him wondering whether he would ever sing again, meeting the legendary Johnny Cash, and recording “Me and God” with bluegrass icon Ralph Stanley.From the songs that changed his life to the moments that nearly ended his career, Josh tells the stories behind his unmistakable voice, his faith, and his journey through country music.Subscribe to the Drifting Cowboy Podcast for honest conversations with the artists, songwriters, musicians, and legends who keep real country music alive.Josh Turner, Josh Turner interview, Josh Turner podcast, Long Black Train, Long Black Train story, story behind Long Black Train, Long Black Train meaning, Your Man Josh Turner, Your Man 20th anniversary, story behind Your Man, Josh Turner vocal cord injury, Josh Turner voice, Josh Turner Johnny Cash, Johnny Cash, Me and God, Ralph Stanley, Josh Turner songs, country music podcast, country music interviews, classic country music, real country music, Drifting Cowboy Podcast, Dillon Weldon
- Sep 3, 20261h 45m
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 the official story.Joining the conversation are renowned Nashville songwriters Gary Gentry, who wrote David Allan Coe’s classic hit “The Ride,” and Bobby Keel, who wrote “Time Off for Bad Behavior.” Together, they revisit the songs, characters and unbelievable road stories surrounding one of the most controversial and fascinating figures in outlaw country music.If you love David Allan Coe, classic country music, outlaw country and true stories told by the people who actually lived them, you don’t want to miss this episode of the Drifting Cowboy Podcast.Subscribe for more honest conversations with the artists, musicians and songwriters who built country music.David Allan Coe, David Allan Coe stories, David Allan Coe band, David Allan Coe documentary, David Allan Coe podcast, outlaw country, outlaw country music, classic country music, country music podcast, The Ride, The Ride David Allan Coe, Gary Gentry, Gary Gentry songwriter, Bobby Keel, Time Off for Bad Behavior, Nashville songwriters, country music stories, country music history, behind the music, road stories, Drifting Cowboy Podcast, Dillon Weldon
- Aug 20, 202651 min
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 years, George’s battle with addiction, how she helped him get sober, and the life they built together away from the spotlight.Nancy also takes us inside George Jones’ friendships with fellow country music legends including Waylon Jennings, Johnny Cash, Johnny Paycheck, and others who were part of their lives during one of the most iconic eras in country music. She shares stories fans have never heard, memories from behind the scenes, the side of George the public rarely got to see, and the remarkable transformation that defined the final decades of his life.The conversation becomes especially emotional as Nancy reflects on George’s final days and shares the story of George Jones’ final words. More than a conversation about a country music legend, this is the story of the man Nancy knew, loved, fought for, and stood beside until the very end.If you grew up listening to George Jones, love classic country music, or have ever wondered what The Possum was really like when the stage lights went off, this is an episode you won’t want to miss.The Real George Jones | Stories Only Nancy Jones Could TellGeorge Jones, Nancy Jones, George Jones interview, Nancy Jones interview, George Jones widow, George Jones wife, The Real George Jones, George Jones stories, George Jones documentary, George Jones podcast, George Jones final words, George Jones death, George Jones sobriety, George Jones addiction, George Jones marriage, George Jones life story, George Jones biography, George Jones The Possum, The Possum, classic country music, country music history, country music legends, traditional country music, old country music, Waylon Jennings, Johnny Cash, Johnny Paycheck, Waylon Jennings stories, Johnny Cash stories, Johnny Paycheck stories, He Stopped Loving Her Today, George Jones He Stopped Loving Her Today, Grand Ole Opry, Nashville country music, country music podcast, Drifting Cowboy Podcast, Drifting Cowboy, country music interviews, country music stories, legendary country singers, outlaw country, real country music
- Aug 13, 20261h 23m
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, influential and unmistakable figures in outlaw country music, writing and recording songs that helped define an era. But behind the music, fame and legendary stories was a complicated family life that few people outside the Coe family ever truly knew.In this emotional conversation, David Allan Coe’s son opens up about discovering who his father was, what it was like knowing his dad was a famous country singer while having virtually no relationship with him, and his attempts to finally make contact. He shares how Johnny Knoxville and a documentary project brought him closer than ever to reaching his father — only for him to open Facebook weeks later and discover that David Allan Coe had died.He also shares his perspective on the complicated relationships surrounding David Allan Coe during the final years of his life, the obstacles he says existed between David and members of his family, and what it feels like to be left with questions that can now never be answered.This isn't simply a collection of David Allan Coe stories. It's the story of a son who wanted the opportunity to know his father — and ran out of time.This episode contains the guest's personal recollections, experiences and perspective. Statements concerning other individuals reflect his account of events and may differ from the recollections or perspectives of others.Subscribe to Drifting Cowboy for more long-form conversations, untold country music stories and firsthand accounts from the artists, songwriters, musicians and families behind country music history.David Allan Coe, David Allan Coe son, David Allan Coe lost son, David Allan Coe children, David Allan Coe family, David Allan Coe interview, David Allan Coe story, David Allan Coe documentary, David Allan Coe death, David Allan Coe wife, David Allan Coe family story, David Allan Coe son interview, David Allan Coe outlaw country, David Allan Coe stories, David Allan Coe podcast, Johnny Knoxville David Allan Coe, Johnny Knoxville documentary, outlaw country, outlaw country music, country music, country music history, country music stories, classic country music, 1970s country music, 1980s country music, Nashville country music, Drifting Cowboy, Drifting Cowboy podcast, country music podcast, untold country music stories, You Never Even Called Me by My Name, The Ride, Would You Lay With Me, Take This Job and Shove It, Willie Nelson, Waylon Jennings, Johnny Cash, George Jones, Merle Haggard
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About Drifting Cowboy
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.
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