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Drifting Cowboy
Dillon Weldon
47 episodes
4 days ago
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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Music Interviews
Music
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All content for Drifting Cowboy is the property of Dillon Weldon and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
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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Music Interviews
Music
Episodes (20/47)
Drifting Cowboy
Alex Miller

Patreon Clip:


https://www.patreon.com/posts/alex-miller-x-142520479?utm_medium=clipboard_copy&utm_source=copyLink&utm_campaign=postshare_creator&utm_content=join_link


From American Idol to sharing the stage with Hank Williams Jr., Tracy Byrd, and Emily Ann Roberts — country artist Alex Miller is living proof that real country music is alive and kicking.In this episode of Drifting Cowboy, Dillon Weldon sits down with Alex to talk about his journey after American Idol, what it’s like recording with Tracy Byrd, performing with Emily Ann Roberts and Belle Frantz, and why traditional country is making a long-awaited comeback.Alex opens up about his roots, his songwriting process, and what it means to stay authentic in a world chasing trends. If you love genuine country storytelling and honky-tonk soul, this one’s for you.Alex Miller, Alex Miller American Idol, Dillon Weldon, Drifting Cowboy Podcast, Emily Ann Roberts, Belle Frantz, Hank Williams Jr., Tracy Byrd, traditional country music, country music comeback, real country music, country podcast, Nashville country, honky tonk, country singer interview, American Idol country singers, modern country music, classic country revival, country storytelling podcast, country artist interviews, Dillon Weldon podcast, country music 2025

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3 days ago
51 minutes 33 seconds

Drifting Cowboy
Blackberry Smoke's Charlie Starr

Blackberry Smoke’s Charlie Starr joins Drifting Cowboy for one of the wildest interviews yet. He opens up about recording with the legendary George Jones, life on the road, and the barroom brawl that left him bloodied with a broken beer bottle and a shard of glass in his head.From unforgettable nights in honky-tonks to lessons learned from icons, Charlie shares raw, unfiltered stories that every country and Southern rock fan needs to hear. Whether you’re a die-hard Blackberry Smoke follower or just love behind-the-scenes stories from the country music world, this episode has it all.


Charlie Starr, Blackberry Smoke, Charlie Starr interview, Blackberry Smoke interview, George Jones stories, George Jones recording, Charlie Starr bar fight, Blackberry Smoke bar fight, country music podcast, Southern rock podcast, Drifting Cowboy podcast, Dillon Weldon podcast, Charlie Starr George Jones, Blackberry Smoke George Jones, Charlie Starr Bloody Bar Fight, Nashville country music stories, Southern rock stories, country music legends

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1 week ago
1 hour 4 minutes 11 seconds

Drifting Cowboy
Craig Campbell

Country star Craig Campbell sits down with Drifting Cowboy for his most unfiltered interview yet. From exposing how Nashville’s big labels really operate, to opening up about his Grindstone Cowboy coffee shops (and the controversy it sparked with the writer of “Rhinestone Cowboy”), Craig doesn’t hold back.We dive into his early days playing piano alongside Luke Bryan and Tracy Byrd, his wild memories opening shows for Merle Haggard, and the lessons he’s learned from years inside country music’s toughest industry machine.If you love real stories straight from the artists who lived them, this is an episode you don’t want to miss.Craig Campbell, Craig Campbell interview, Craig Campbell podcast, Grindstone Cowboy coffee, Rhinestone Cowboy controversy, Nashville record labels, country music industry secrets, country music podcast, Craig Campbell Luke Bryan, Craig Campbell Tracy Byrd, Craig Campbell Merle Haggard, Nashville country music, country music podcast 2025, Drifting Cowboy podcast, Dillon Weldon podcast

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2 weeks ago
46 minutes

Drifting Cowboy
Joe Nichols

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

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3 weeks ago
1 hour 15 minutes 7 seconds

Drifting Cowboy
Marcus King

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

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1 month ago
44 minutes 52 seconds

Drifting Cowboy
Dusty Slay

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



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1 month ago
1 hour 21 seconds

Drifting Cowboy
Shooter Jennings

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

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1 month ago
1 hour 29 minutes 13 seconds

Drifting Cowboy
William Lee Golden of The Oak Ridge Boys

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

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2 months ago
1 hour 9 minutes 15 seconds

Drifting Cowboy
Ben and Noel Haggard

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

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2 months ago
32 minutes 29 seconds

Drifting Cowboy
Keith Stegall, Roger Murrah and Jim McBride

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 music


If 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

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2 months ago
1 hour 4 minutes 40 seconds

Drifting Cowboy
Larry Gatlin

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

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2 months ago
1 hour 42 minutes 11 seconds

Drifting Cowboy
Sam Williams

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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2 months ago
48 minutes 17 seconds

Drifting Cowboy
Murder on Music Row: Sammy Sadler's Story

In this powerful episode, country artist Sammy Sadler opens up about his remarkable career, the infamous "Murder on Music Row", and how the tragic event changed the course of his life. From his rise in the '80s country scene to surviving one of Nashville’s darkest moments, Sammy shares raw insights, untold stories, and what’s next in his musical journey. Don’t miss this emotional and revealing conversation with one of country music’s most resilient voices.Sammy Sadler, Murder on Music Row, country music podcast, country music history, Nashville murder, country music interviews, true crime in country music, 80s country music, country music stories, Drifting Cowboy Podcast, country music legends, Sammy Sadler interview, country music Nashville, Music Row history, country music documentary.

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3 months ago
26 minutes 33 seconds

Drifting Cowboy
Jamey Johnson

Jamey Johnson joins Dillon Weldon for one of his funniest and most candid interviews to date. They swap stories about Hank Cochran, Dean Dillon, Willie Nelson, and Toby Keith, and Jamey shares hilarious behind-the-scenes moments from his wild journey through country music. It’s a rare glimpse into the lighter side of one of the genre’s most respected voices.

Hit that like button, subscribe, and let us know your favorite story in the comments!

#JameyJohnson #CountryMusicPodcast #OutlawCountry #WillieNelson #DeanDillon #RealCountry #DillonWeldon #TobyKeith #HankCochran #CountryMusicLegends #DriftingCowboyPodcast #TraditionalCountry #ClassicCountry #JameyJohnsonInterview #CountryStorytelling

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3 months ago
1 hour 12 minutes 27 seconds

Drifting Cowboy
Mac McAnally

In this episode of the Drifting Cowboy Podcast, legendary songwriter and musician Mac McAnally shares wild behind-the-scenes stories from life on the road with Jimmy Buffett, his early days growing up in Mississippi, and how he first got into music. Mac opens up about his close friendship with Buffett, memories of country icons like John Prine and Toby Keith, and the songwriting journey that led to countless hits. If you're a fan of heartfelt stories, classic songwriting, and country music legends—this one's for you.

🎙️ Topics Covered:

  • Touring and recording with Jimmy Buffett

  • Mac’s Southern childhood and musical roots

  • Stories about John Prine and Toby Keith

  • Songwriting insights and industry secrets

📌 Don’t forget to like, comment, and subscribe for more stories from the legends of country music!

#MacMcAnally #JimmyBuffett #CountryMusicPodcast #JohnPrine #TobyKeith #DriftingCowboyPodcast #SongwritersCircle #SouthernStorytelling

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4 months ago
1 hour 13 minutes 54 seconds

Drifting Cowboy
Special Episode: Tyler White of Love on the Spectrum

Tyler White, best known for his appearance on Love on the Spectrum, had no idea that agreeing to do a podcast would lead to the biggest surprise of his life — a moment on the Grand Ole Opry stage.This documentary-style special of the Drifting Cowboy podcast takes you behind the scenes of a once-in-a-lifetime journey: from a heartfelt podcast conversation to a standing ovation at country music’s most sacred stage.You’ll witness the raw emotion, the nerves, the music, and the magic — all building to a powerful moment that Tyler will never forget.This is more than just a story about music. It’s about dreams coming true, inclusion, and how a single act of kindness can ripple through an entire industry.🎙️ Hosted by Dillon Weldon (Drifting Cowboy Podcast)🎵 Featuring: Tyler White, Randy Travis, Eryn Cooper (WSM), and the Grand Ole Opry family📍 Filmed in Nashville, Tennessee💬 If this moved you, please like, comment, and share to help spread Tyler’s story to the world.#LoveOnTheSpectrum #GrandOleOpry #TylerWhite #CountryMusic #AutismAwareness #InclusionMatters #DriftingCowboyPodcast #SurpriseMoment

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4 months ago
21 minutes 21 seconds

Drifting Cowboy
Lukas Nelson

Lukas Nelson joins the Drifting Cowboy podcast for an unforgettable conversation. He shares the moment Kris Kristofferson told him, “You have no choice but to write songs,” and opens up about the weight of legacy, songwriting, and forging his own path in music. Lukas also talks about working on A Star Is Born, becoming a licensed pilot, and even plays a little music live during the show.🎙️ Hear stories about growing up as Willie Nelson’s son, country music legends, and what Lukas has planned next.🔥 Subscribe for more rare interviews, wild stories, and music history straight from the legends themselves.Tags: Lukas Nelson interview, Kris Kristofferson songwriting, A Star Is Born Lukas Nelson, Lukas Nelson pilot, Willie Nelson family, Lukas Nelson music, country music podcast, Drifting Cowboy, Lukas Nelson 2025, live music podcast, outlaw country stories, country music storytelling

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4 months ago
45 minutes 14 seconds

Drifting Cowboy
Clay Walker

In this episode of the Drifting Cowboy Podcast, Clay Walker sits down with Dillon to share deeply personal and never-before-heard stories from his legendary country music career.From the emotional moment when Merle Haggard broke down in tears on stage, to wild memories with George Jones and Johnny Paycheck, Clay gives an unfiltered look at the legends of country music — and the real-life moments that shaped them.Clay also opens up about his ongoing battle with multiple sclerosis, the faith that keeps him grounded, and what it truly means to endure in the world of country music, as well as the upcoming biopic on Randy Travis' life, where Clay will portray Randy.🎙️ Topics Covered:• Merle Haggard's emotional duet with Clay• Wild stories about George Jones and Johnny Paycheck• Clay’s MS diagnosis and life perspective• Behind-the-scenes of his biggest hits and career🔔 Subscribe for more legendary country music stories, interviews, and behind-the-scenes moments.#ClayWalker #MerleHaggard #GeorgeJones #JohnnyPaycheck #CountryMusicPodcast #DriftingCowboyPodcast #RandyTravis #movie

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5 months ago
1 hour 15 minutes 4 seconds

Drifting Cowboy
Cledus T. Judd

🎙️ In this explosive episode, country comedy legend Cledus T. Judd opens up like never before. From getting hit with cease and desist letters from Michael Jackson and Don Henley, to battling frostbite during his early days, his friendship with Toby Keith, and having his heart broken by the Grand Ole Opry — this is the raw, unfiltered story behind country music’s most beloved parody artist.We dive deep into the highs and lows of his caree, and what it really takes to survive in the music industry when you're pushing boundaries. Whether you’re a longtime fan or just discovering Cledus, you won’t believe the stories he shares.#CledusTJudd #MichaelJackson #CountryMusicPodcast #DonHenley #GrandOleOpry #CountryComedy #DriftingCowboyPodcast #MusicIndustry #BehindTheScenes

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5 months ago
1 hour 12 minutes 39 seconds

Drifting Cowboy
Ray Wylie Hubbard

Ray Wylie Hubbard sits down for a raw, unfiltered conversation about the legendary outlaw country era — sharing personal stories about Willie Nelson, Waylon Jennings, Townes Van Zandt, Guy Clark, Blaze Foley, and Jerry Jeff Walker.From the chaos of the road to the poetry of songwriting, Ray reveals what really went down during country music’s most untamed era.👉 Don’t forget to like, comment, and subscribe for more untold country stories from the people who lived them.

🎙️ The Drifting Cowboy Podcast

🔔 New episodes every week

📍 Filmed in Nashville, TN


Ray Wylie Hubbard, Willie Nelson, Waylon Jennings, Townes Van Zandt, Guy Clark, Blaze Foley, Jerry Jeff Walker, outlaw country, country music podcast, Ray Wylie interview, country legends, wildest era in country music, Drifting Cowboy Podcast, Nashville podcast, Texas country, Americana music, songwriter stories, country music history, southern storytelling, country music 2025

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5 months ago
1 hour 1 minute 48 seconds

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.