Bernie Leadon (Founding Member of The Eagles)

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 five

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

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

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

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