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Drifting Cowboy

Author: Dillon Weldon

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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.
45 Episodes
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T. Graham Brown

T. Graham Brown

2024-12-2248:25

In this episode, I sit down with country music legend T. Graham Brown. We talk about everything from Keith Whitley to addiction to faith. I hope you enjoy and I appreciate y'all!
TG Sheppard and Payton Dale

TG Sheppard and Payton Dale

2024-11-2601:14:15

In this episode, I have a conversation with country music legend TG Sheppard and his daughter, Payton Dale. We talk about everything from Elvis Presley to fashion to Waylon Jennings. Check out the Patreon exclusive segment at patreon.com/dillonweldon
Elizabeth Cook

Elizabeth Cook

2024-10-1152:25

In this episode of Drifting Cowboy Podcast, Dillon interviews Elizabeth Cook. Elizabeth is a very successful singer, songwriter, radio personality, voice actor, and so much more!
Bobby Braddock

Bobby Braddock

2024-08-0156:52

In this episode, we talk to legendary songwriter and producer Bobby Braddock. Bobby wrote many hit songs such as He Stopped Loving Her Today, D-I-V-O-R-C-E, Golden Ring, Texas Tornado, Time Marches On and more.
Gary Gentry

Gary Gentry

2024-05-2201:06:15

Gary Gentry is the legendary songwriter behind hits like The Ride, The One I Loved Back Then, 1959, The Chicken in Black and so many more. In this podcast, we discuss the stories behind the songs.
John Paycheck

John Paycheck

2024-05-1549:34

John Paycheck is the son of country music legend, Johnny Paycheck. This podcast was conducted the day after John's Grand Ole Opry debut for his father's tribute show. Recorded at Johnny Cash's farm in Bon Aqua, TN.
Dale Watson

Dale Watson

2024-01-0701:06:47

Dale Watson is the founder of the Ameripolitan music genre as well as the Ameripolitan music awards. www.ameripolitan.org
Welcome back to another episode of Drifting Cowboy. In this episode we have special guest Dillan Holliday and we take a dive into some of country music's eeriest, ghostly stories. Hosted by Dillon Weldon, who you can find on TikTok, Facebook, Instagram and YouTube for even more country music content.
In this episode of Drifting Cowboy, we will be discussing the life of legendary songwriter, Townes Van Zandt. Thank you all for listening. You can find more country music content from the host, Dillon Weldon, on TikTok, Instagram and Facebook.
This episode covers the troubled life of country music legend Tammy Wynette, narrating the trials and tribulations of her life. Tammy’s life gives us a glimpse of how even the most successful and talented artists could have a life blanketed with sorrow. Drifting Cowboy is hosted by Dillon Weldon. For more of Dillon's content, check out his TikTok, Facebook, Instagram, and YouTube pages. Thanks for listening.
This episode of Drifting Cowboy explores the events that led up to the death of Hank Williams. We have special guest and grandson of Ray Price, Gary Jones, Jr. as well as music from Tim Goodin. Hosted by Dillon Weldon. You can find more country music content from Dillon on his TikTok, Facebook, Instagram, and YouTube pages. Thanks for listening!
Joe Nichols

Joe Nichols

2025-10-0901:15:07

Joe Nichols sits down for one of his most revealing interviews yet. In this episode of The Drifting Cowboy Podcast, Joe tells all—opening up about his struggles with addiction, why he once thought he wouldn’t live past 25, and how sobriety changed everything.But it’s not all heavy. Joe also shares hilarious stories about smoking pot with Gary Allan, hunting trips with Hank Williams Jr., and the wild life of being a young country star on the road. From heartache to humor, this episode shows a side of Joe Nichols fans have never heard before.If you love real stories from country music legends—equal parts raw and entertaining—you don’t want to miss this conversation.🔔 Subscribe for more in-depth interviews and country music storytelling with today’s biggest and most legendary artists.Joe Nichols interview, Joe Nichols podcast, Joe Nichols tells all, Joe Nichols addiction, Joe Nichols sobriety, Joe Nichols wanted to die young, Joe Nichols Hank Jr., Joe Nichols Gary Allan, Joe Nichols hunting, Joe Nichols country music, Joe Nichols 2025, Joe Nichols funny stories, Joe Nichols untold story, Joe Nichols live interview, Drifting Cowboy podcast, Dillon Weldon
Marcus King

Marcus King

2025-10-0244:52

Marcus King sits down for an honest, unfiltered conversation about his struggles with addiction, his journey to sobriety, the influence of music in his life, and how love gave him a new sense of purpose. In this exclusive interview, Marcus opens up about the battles he’s faced, the artists who inspired him, and the role his wife Briley has played in his story.From raw truths about the music industry to heartfelt reflections on recovery and resilience, this is Marcus King like you’ve never seen him before. Whether you’re a fan of his music, interested in stories of overcoming addiction, or simply looking for inspiration, this episode delivers.🔔 Subscribe for more in-depth country music interviews, stories, and behind-the-scenes conversations with today’s most important artists.Marcus King interview, Marcus King podcast, Marcus King sobriety, Marcus King addiction, Marcus King Briley, Marcus King wife, Marcus King story, Marcus King opens up, Marcus King country music, Marcus King live, Marcus King love story, Marcus King struggles, Marcus King music influences, Marcus King 2025 interview, Drifting Cowboy podcast, Dillon Weldon
Dusty Slay

Dusty Slay

2025-09-2501:00:21

Dusty Slay joins me for one of the funniest podcasts I’ve ever recorded.We go deep on country music, ask the burning question of what McDonald’s beef really is, trade insane stories, and I even get something off my chest. This episode is hilarious, raw, and guaranteed to make you laugh while maybe teaching you a thing or two.Dusty is one of the sharpest comedians in the game, and mixing his humor with country music talk made for pure gold. If you love stand-up, country music, or just want to hear two guys crack each other up about life, this is your jam.👉 Don’t forget to like, comment, and subscribe for more podcasts!#DustySlay #CountryMusic #ComedyPodcast #StandupComedy #FunnyPodcast #McDonalds #AirbnbStories #CountryMusicPodcast #HilariousPodcast #ComediansTalking #PodcastClips #DriftingCowboyPodcast #DustySlayPodcast
Shooter Jennings

Shooter Jennings

2025-09-1701:29:13

Shooter Jennings joins the Drifting Cowboy Podcast for an unfiltered conversation about his father Waylon Jennings, the spirit of Outlaw Country, and the legacy that still shakes Nashville today. We dive into never-before-heard stories about Waylon and Jessi Colter, reflections on Johnny Cash, and the future of artists like Charley Crockett who are carrying the torch. Shooter also gives insight into the new Waylon albums and what they mean for fans of real country music.This episode is packed with history, storytelling, and Shooter’s own perspective on where country music has been—and where it’s headed. If you love Outlaw Country, you won’t want to miss this one.Shooter Jennings, Waylon Jennings, Outlaw Country, Johnny Cash, Jessi Colter, Charley Crockett, Drifting Cowboy Podcast, Waylon Jennings albums, Waylon Jennings new albums, Shooter Jennings interview, country music podcast, outlaw country music, Waylon Jennings legacy, Shooter Jennings Waylon, classic country music, outlaw country revival
Step inside the life and legacy of William Lee Golden—the legendary Oak Ridge Boy with the iconic beard. In this exclusive conversation, we dive into untold stories of the Oak Ridge Boys, behind-the-scenes moments from country music history, the making of classic hits, and the family project that’s redefining his career, The Goldens.We talk about his brand-new book, his time on the road, and even how The Dukes of Hazzard crossed paths with the Oaks. From timeless gospel harmonies to rowdy country hits, William Lee Golden opens up about a life lived at the heart of American music.If you love country music history, storytelling, and the legends who shaped it, this is one you don’t want to miss.William Lee Golden, Oak Ridge Boys, Untold Stories Oak Ridge Boys, Oak Ridge Boys interview, William Lee Golden interview, The Goldens band, William Lee Golden book, Dukes of Hazzard Oak Ridge Boys, Oak Ridge Boys hits, Elvira Oak Ridge Boys, Classic country music, Country music legends, Outlaw country stories, Gospel country music, Country music podcast, Drifting Cowboy Podcast
Ben and Noel Haggard

Ben and Noel Haggard

2025-08-2732:29

In this episode of Drifting Cowboy, I sit down with Ben and Noel Haggard—sons of the legendary Merle Haggard—for an unforgettable conversation filled with stories, laughs, and behind-the-scenes memories. We talk about their father’s legacy, growing up in the shadow of a country music giant, and their personal experiences with icons like Kris Kristofferson and The Eagles. From road tales to rare family insights, this episode is a treasure chest for any true country music fan.If you love country music history, untold stories from the road, and a raw glimpse into the Haggard family’s life, you won’t want to miss this one.Merle Haggard, Ben Haggard, Noel Haggard, Drifting Cowboy Podcast, Kris Kristofferson, The Eagles, Country Music Stories, Country Music Legends, Haggard Family, Classic Country, Country Music History, Country Podcast, Drifting Cowboy, Dillon Weldon
Alan Jackson’s career wouldn’t be the same without Keith Stegall, Roger Murrah, and Jim McBride—the powerhouse trio behind some of his biggest hits. From “Chattahoochee” and “Don’t Rock the Jukebox” to “Chasin’ That Neon Rainbow,” “Dallas,” and more, these men helped shape one of the greatest careers in country music.In this episode of Drifting Cowboy, I sit down with these legends to talk about:✅ The stories behind Alan’s iconic songs✅ How they met and began working with Alan✅ Keith Stegall’s role as Alan’s longtime producer✅ Memories from the early days of Alan’s career✅ The impact Alan Jackson made on country musicIf you love country music history, songwriting stories, and behind-the-scenes insight into Alan Jackson’s rise to fame—you won’t want to miss this one.alan jackson, alan jackson interview, alan jackson hits, alan jackson chattahoochee, alan jackson dont rock the jukebox, alan jackson chasing that neon rainbow, alan jackson dallas, alan jackson keith stegall, alan jackson jim mcbride, alan jackson roger murrah, alan jackson producer, alan jackson songwriter stories, alan jackson documentary, drifting cowboy podcast, country music history, country music podcast, 90s country music
Larry Gatlin

Larry Gatlin

2025-08-1301:42:11

Country music legend Larry Gatlin sits down with Dillon Weldon for an unforgettable conversation about his decades-long career, songwriting with his brothers, behind-the-scenes Opry stories, and the wild ride from Texas honky-tonks to the Grand Ole Opry stage. Hear Larry like you’ve never heard him before — full of heart, humor, and country music wisdom. If you love real stories from the legends themselves, this one’s a must-listen.Larry Gatlin, Larry Gatlin interview, Gatlin Brothers, Larry Gatlin podcast, Grand Ole Opry stories, country music legends, country music history, Texas country music, classic country, country music interviews, Dillon Weldon podcast, Drifting Cowboy podcast, country songwriter stories, Opry interviews, Nashville country music
Sam Williams

Sam Williams

2025-08-0648:17

Full Interview with Sam Williams | The Drifting Cowboy PodcastIn this episode of The Drifting Cowboy, Sam Williams — grandson of Hank Williams and son of Hank Jr. — sits down for an unforgettable conversation about life, legacy, and blazing his own trail in country music. Sam opens up about the pressure of carrying the Williams name, the wisdom passed down from his legendary father and grandfather, and his relationship with Merle Kilgore, co-writer of “Ring of Fire” and longtime family friend. But this isn’t just about the past.Sam is a creative force of his own, pushing boundaries and reimagining what music can be. With haunting lyrics, genre-bending style, and raw emotional honesty, Sam is proving he’s not just continuing the legacy — he’s evolving it.If you care about country music history and its future, you won’t want to miss this.Subscribe for more interviews with country legends and the voices shaping tomorrow’s sound.sam williams interview, hank williams grandson, hank williams jr son, sam williams podcast, drifting cowboy podcast, country music legacy, merle kilgore, sam williams country music, innovator in country music, sam williams music, outlaw country, new country artists, country music storytelling, sam williams 2025, country music family dynasty
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