MusicMusic Interviews

Drifting Cowboy

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.

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Thursday · 1 hr 3 min
Lacy J. Dalton Exposes the Record Executive Who Tried to Destroy Her
Country music legend Lacy J. Dalton opens up about the record executive she says tried to destroy her career, revealing the shocking story of what happened behind the scenes at Columbia Records. In this revealing episode of The Drifting Cowboy Podcast, Lacy J. Dalton shares her remarkable journey through country music, from her early beginnings in the industry to becoming one of the most recognizable voices of the 1980s. At the heart of this conversation is Lacy's troubled relationship with Columbia Records executive Rick Blackburn. Lacy reveals how a personal grudge allegedly turned into a campaign to undermine her career, including Blackburn's refusal to properly promote her records. In her own words, "He hated me" and "He tried to destroy me." It's a powerful firsthand account of how the politics of Nashville's music industry could shape—and sometimes derail—an artist's future. But there's much more to Lacy's story. She reflects on her early days in the music business, her relationship with legendary producer Billy Sherrill, and the pivotal role he played in helping launch her career. She also shares memories of working alongside country music icons including Bobby Bare, Kris Kristofferson, and Hoyt Axton, as well as her experiences with influential Nashville producers and executives Jimmy Bowen and James Stroud. From the glory days of traditional country music to the harsh realities of the record business, Lacy offers an unfiltered look at the people, decisions, and relationships that shaped her extraordinary career. This is a conversation about music, power, betrayal, perseverance, and the price of standing your ground in Nashville. If you love classic country music, the history of Nashville, and untold stories from the legends who lived it, this is an episode you won't want to miss. Subscribe to The Drifting Cowboy Podcast for more in-depth conversations with the artists, songwriters, and legends who made country music what it is today. #LacyJDalton #CountryMusicHistory #ClassicCountryMusic #DriftingCowboyPodcast #NashvilleMusic
October 20 · 1 hr 7 min
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 five Playing onstage with bluegrass pioneer Bill Monroe at just six years old Performing "Ruby" with Flatt and Scruggs on the Martha White Flour Hour at age seven Meeting Keith Whitley and the beginning of their lifelong friendship What Keith Whitley was really like away from the spotlight Playing bluegrass with Keith Whitley and Ralph Stanley The heartbreaking news of Keith Whitley's death His journey from bluegrass prodigy to country music superstar The unbelievable first-class airplane encounter that helped launch his recording career And 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
October 15 · 1 hr 10 min
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
October 1 · 1 hr 8 min
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
September 24 · 1 hr 1 min
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
September 10 · 46 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
September 3 · 1 hr 45 min
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
August 20 · 51 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 Tell George 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
August 13 · 1 hr 23 min
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
August 6 · 46 min
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, struggles, and creative brilliance behind one of country music’s most original careers. He also shares personal stories involving Johnny Cash, Willie Nelson, and other legendary figures who crossed paths with Roger throughout his life. Roger Miller changed country music with songs like “King of the Road,” “Dang Me,” “Chug-a-Lug,” and “England Swings.” Behind those classics was a gifted songwriter, fearless entertainer, devoted friend, and wonderfully complicated man. This conversation offers a rare look at Roger through the eyes of his son, revealing the personality and private moments that fans never got to see. Subscribe for more untold stories from the artists, songwriters, musicians, and families who helped shape country music history. Roger Miller, Dean Miller, Roger Miller son, Roger Miller interview, Roger Miller stories, Roger Miller documentary, Roger Miller biography, what Roger Miller was really like, King of the Road, Dang Me, Chug a Lug, England Swings, Johnny Cash, Willie Nelson, Johnny Cash stories, Willie Nelson stories, classic country music, country music legends, country music history, Nashville history, Nashville songwriters, Grand Ole Opry, vintage country music, country music podcast, music history podcast, celebrity children interviews, sons of country music legends, untold country music stories, behind the music, songwriter stories, Drifting Cowboy Podcast, Dillon Weldon, Dean Miller interview
July 30 · 56 min
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 country music history. They share stories about growing up around the Statler Brothers, Johnny Cash cooking at their house, a wild night in a Canadian jail, Roy Acuff stealing catered food from their television show, and plenty more that has rarely—if ever—been told publicly. This is more than an interview. It’s four generations of memories, laughter, family history, and behind-the-scenes stories from one of country music’s most beloved groups. Watch until the end, subscribe to Drifting Cowboy, and tell us in the comments: What is your favorite Statler Brothers song or memory? Wilson Fairchild, Statler Brothers, Johnny Cash, Don Reid, Harold Reid, Statler Brothers stories, Johnny Cash stories, country music history, classic country music, country music legends, Drifting Cowboy podcast, Roy Acuff, Statler Brothers interview, Wilson Fairchild interview, country music podcast, Flowers on the Wall, Bed of Rose’s, gospel country music, Grand Ole Opry, Nashville history, behind the music, untold country music stories
July 16 · 1 hr 7 min
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 fame that happened almost overnight. She also shares stories about her friendship with David Allan Coe and how he pitched her “Would You Lay with Me (In a Field of Stone),” meeting Gary Stewart and Dean Dillon, writing “Leave Them Boys Alone,” appearing in Jeremiah Johnson, and navigating country music as one of its youngest and most unforgettable stars. This conversation is a rare firsthand look at the songs, people, and moments that shaped Tanya Tucker’s legendary career. Subscribe to the Drifting Cowboy Podcast for more unfiltered conversations with the artists, songwriters, musicians, and characters who built country music. Tanya Tucker, Tanya Tucker interview, Tanya Tucker podcast, Tanya Tucker Delta Dawn, Delta Dawn story, how Tanya Tucker became famous, Tanya Tucker age 13, Billy Sherrill, David Allan Coe, Would You Lay With Me In a Field of Stone, Field of Stone, Gary Stewart, Dean Dillon, Leave Them Boys Alone, Jeremiah Johnson, classic country music, country music history, country music legends, 1970s country music, female country singers, Nashville history, country music podcast, Drifting Cowboy Podcast, Dillon Weldon, Tanya Tucker songs, Tanya Tucker career, Tanya Tucker documentary, country music interview, legendary country singers
July 9 · 34 min
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 in Jim Stafford’s basement with comedian Gallagher, and the crazy road stories that came with touring alongside legends like Conway Twitty, Merle Haggard, George Jones, and more. From “Let Your Love Flow” to decades of life on the road, The Bellamy Brothers open up about the outlaw side of country music, the strange turns that shaped their career, and the stories most fans have never heard. This is a hilarious, honest, and unforgettable look inside the real lives of two country music legends who lived through one of the wildest eras in American music. The Bellamy Brothers, Bellamy Brothers interview, Howard Bellamy, David Bellamy, Drifting Cowboy, Dillon Weldon, country music podcast, country music interview, classic country music, outlaw country, country music legends, Let Your Love Flow, Redneck Girl, Old Hippie, Bellamy Brothers stories, Bellamy Brothers podcast, Conway Twitty stories, Merle Haggard stories, George Jones stories, Jim Stafford, Gallagher comedian, 1970s country music, 1980s country music, Florida country music, country music history, wild country music stories, country artists interview, Nashville stories, country music documentary, classic country podcast, best country music podcast, old school country music, real country music, country legends interview, country music road stories, country singer stories, Drifting Cowboy podcast, Bellamy Brothers full interview
June 26 · 42 min
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 Chris LeDoux — rodeo champion, country music legend, and one of the most electric live performers to ever step on a stage. In this conversation, Ned tells stories from inside Chris LeDoux’s band, from mechanical bulls and pyrotechnics on stage to the wild energy of those legendary concerts. He also opens up about finishing some of his dad’s unfinished songs, building his own path in country music, and working with Mac McAnally to help bring those songs to life. Ned also talks about Chris LeDoux’s friendship with Garth Brooks, the impact Garth had on introducing Chris to a wider country audience, and why Chris LeDoux remains one of the most beloved and authentic figures in country music history. This is a conversation about family, rodeo, country music, legacy, and the kind of performer they simply don’t make anymore. Subscribe for more long-form conversations with country music legends, songwriters, and the people who lived the stories behind the songs. #NedLeDoux #ChrisLeDoux #CountryMusic Ned LeDoux, Chris LeDoux, Chris LeDoux interview, Ned LeDoux interview, Ned LeDoux music video, new Ned LeDoux music, Chris LeDoux stories, Chris LeDoux concerts, Chris LeDoux live, Chris LeDoux mechanical bull, Chris LeDoux pyrotechnics, Chris LeDoux rodeo, 1976 bareback champion, rodeo country music, country music podcast, Drifting Cowboy, country music interviews, classic country, real country music, Garth Brooks Chris LeDoux, Chris LeDoux Garth Brooks friendship, Mac McAnally, Ned LeDoux songs, finishing Chris LeDoux songs, Chris LeDoux legacy, western music, cowboy country music, country music legends, untold country music stories, country music history, rodeo champion singer, Chris LeDoux band, life on the road country music
June 18 · 44 min
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 like behind closed doors, and the legacy that still follows the Jennings name today. We also dive into Whey's own journey through addiction, hitting rock bottom, getting sober, and building a music career on his own terms. From family stories and outlaw country history to redemption, faith, and second chances, this is one of the most honest conversations we've had on the podcast. If you're a fan of Waylon Jennings, outlaw country, classic country music, or powerful comeback stories, this episode is for you. #WaylonJennings #WheyJennings #OutlawCountry #CountryMusic #DriftingCowboyPodcast Waylon Jennings, Whey Jennings, Jessi Colter, outlaw country, country music podcast, Waylon Jennings stories, what Waylon Jennings was really like, Whey Jennings interview, Waylon Jennings grandson, country music history, classic country music, outlaw movement, Nashville podcast, country singer interview, sobriety story, addiction recovery, getting sober, redemption story, country music legends, Drifting Cowboy Podcast, Jesse Keith Whitley, Johnny Cash, Willie Nelson, Hank Williams Jr, Merle Haggard, country music conversation, behind the music, country music documentary, country music fans, outlaw country music
June 11 · 53 min
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 Stuart, working with Miranda Lambert, his experience on The Voice, and why traditional country music still matters. From hilarious backstage moments to honest conversations about country music's past and future, this is one of the most entertaining Jake Worthington interviews you'll hear.If you enjoy stories about classic country music, Daryle Singletary, George Jones, Merle Haggard, Marty Stuart, Miranda Lambert, and the artists keeping traditional country alive, be sure to like, subscribe, and share the episode.#JakeWorthington #DaryleSingletary #CountryMusic #DriftingCowboyPodcastJake Worthington, Daryle Singletary, Jake Worthington interview, Daryle Singletary story, country music podcast, traditional country music, Marty Stuart, Miranda Lambert, The Voice, classic country, outlaw country, Texas country, country singer podcast, George Jones, Merle Haggard, Randy Travis, Alan Jackson, Nashville, country music stories, country music legends, Drifting Cowboy Podcast, Dillon Weldon, country music interview, country music history, neotraditional country, Grand Ole Opry, country music fans, country music conversation, country music documentary, country music storytelling, western music, honky tonk music, country music culture, classic country stories, Jake Worthington podcast, Daryle Singletary interview, traditional country singer, country music YouTube, country music fans podcast, Nashville podcast, country music legends stories, country music entertainment, old school country music, country music discussion, country music community, country music heritage, Texas honky tonk, country music industry, country music history podcast
June 1 · 23 min
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 country radio stopped supporting his music after he became outspoken about politics. Aaron also shares stories about his friendship with Charlie Daniels, the making of “Country Boy” with Charlie Daniels and George Jones, and what it was like bringing rock, country, and real-life conviction into the same room.From Staind’s rise to country radio controversy, Aaron Lewis does not hold back. Topics include:Aaron Lewis on Staind, the origins of Staind, rock music vs country music, country radio, politics in country music, Charlie Daniels, George Jones, Country Boy, Aaron Lewis solo career, being blackballed by country radio, and the real difference between rock fans and country fans. Aaron Lewis, Aaron Lewis interview, Aaron Lewis podcast, Aaron Lewis country radio, Aaron Lewis blackballed, Aaron Lewis politics, Aaron Lewis Staind, Staind, Staind interview, Aaron Lewis Country Boy, Country Boy Aaron Lewis, Charlie Daniels, George Jones, Charlie Daniels Aaron Lewis, Aaron Lewis George Jones, country radio controversy, country music podcast, country music interview, Drifting Cowboy podcast, Dillon Weldon, country music stories, outlaw country, rock star to country star, Aaron Lewis country music, Aaron Lewis That Ain’t Country, Aaron Lewis Am I The Only One, Staind origin story, country music politics, country radio politics, why country radio won’t play Aaron Lewis, Aaron Lewis says country radio blackballed him, best Aaron Lewis interview, country boy with Charlie Daniels and George Jones, country music news, country music documentary, Nashville country radio, modern country music, real country music, classic country, rock music podcast, country artist interview, viral country music interview, Aaron Lewis full interview
May 29 · 47 min
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 Nashville, the growing demand for authentic country music, and why so many young fans are embracing traditional sounds again. If you're a fan of George Strait, Alan Jackson, Randy Travis, Zach Top, Cody Johnson, and classic country music, this is an episode you won't want to miss.🔔 Subscribe for more conversations with country music legends, rising stars, songwriters, and the people who shaped country music history.Follow Drifting Cowboy:[Insert Links]Follow Braxton Keith:[Insert Links]#CountryMusic #BraxtonKeith #TraditionalCountryBraxton Keith, Braxton Keith podcast, Braxton Keith interview, traditional country music, country music podcast, Drifting Cowboy Podcast, country music history, honky tonk music, Texas country music, neo traditional country, traditional country comeback, country music 2026, George Strait, Alan Jackson, Randy Travis, Zach Top, Cody Johnson, classic country music, outlaw country, country singer interview, Nashville, Texas country, country music fans, country music conversation, country music legends, rising country stars, real country music, country music industry, western music, honky tonks, country artists, country music stories, country music culture, country music community, new country music, independent country music, country music discussion, country music podcast interview, country music revival, country music comeback, Drifting Cowboy, Dillon Weldon, Braxton Keith country music, traditional country revival, modern country music, country music trends, country music influencers, country lifestyle, country western music, classic country sound, authentic country music, country music fans podcast, Braxton Keith 2026, country music interview podcast
May 21 · 43 min
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 control that changed his career forever. Clint also shares incredible stories about Merle Haggard, Waylon Jennings, Jimmy Buffett, songwriting, the Nashville machine, and the era that changed country music forever. Plus, he discusses his brand-new book and reflects on the highs, pressures, and realities of becoming one of the biggest stars of the 1990s. This is Clint Black like you’ve rarely heard him before — honest, reflective, funny, and completely unfiltered. #ClintBlack #CountryMusic #MerleHaggard #WaylonJennings #JimmyBuffett #90sCountry #OutlawCountry #Nashville #CountryMusicPodcast #DriftingCowboy clint black, clint black interview, why clint black walked away, clint black rca records, clint black podcast, drifting cowboy podcast, country music podcast, merle haggard stories, waylon jennings stories, jimmy buffett stories, clint black new book, 90s country music, outlaw country, country music legends, nashville music, country music history, killin time clint black, clint black songs, classic country music, george strait, alan jackson, country music interviews, country singer podcast, texas country music, merle haggard, waylon jennings, jimmy buffett
May 15 · 31 min
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. Paul also talks about his family’s connection to Hank Williams, outlaw country music, songwriting, life on the road, and the legends that shaped country music history. If you love classic country stories, rare behind-the-scenes moments, and deep conversations about the artists who built country music, this episode is for you. kris kristofferson, johnny cash, paul cauthen, hank williams, country music podcast, drifting cowboy podcast, outlaw country, classic country music, kris kristofferson interview, johnny cash stories, country music history, hank williams stories, country legends, nashville podcast, texas country music, songwriter stories, old country music, willie nelson, waylon jennings, merle haggard, country music interviews, music history, kris kristofferson lyme disease, paul cauthen interview, johnny cash podcast, country music documentary, country music fans, americana music, red dirt country, country storytelling

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