Drifting Cowboy

Whisperin’ Bill Anderson joins The Drifting Cowboy Podcast for a deep dive into one of the most legendary careers in country music history. From writing timeless songs like Whiskey Lullaby and Give It Away to sharing the stage with icons like Roger Miller and Faron Young, Bill opens up about the stories, struggles, and moments that shaped a lifetime of hits. He also talks about hosting Country Fam...

Founding Eagles member Bernie Leadon joins me to share the real story behind one of the most important chapters in American music. Bernie talks about his early years with Gram Parsons and the Flying Burrito Brothers, his memories from Altamont Speedway, and the musical and personal moments that shaped the rise of The Eagles. We dive deep into writing classics like “Witchy Woman,” the band’s early...

Legendary harmonica player Mickey Raphael joins me for a deep dive into life on the road with Willie Nelson — including an unbelievable story about the night Willie’s crew ended up getting a ride to a show from the Hells Angels. Mickey also talks about working with iconic songwriters like Guy Clark and Townes Van Zandt, his memories from decades of touring, his solo projects, and the exciting new...

Join Patreon for Exclusive Content:https://patreon.com/DillonWeldon?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_creator&utm_content=copyLinkStep inside the world of Waylon Jennings like you’ve never heard it before. In this episode, the legendary members of Waylon’s band sit down and tell ALL — the untold, unbelievable, and downright wild stories from life on the...

Sign Up on Patreon for Exclusive Content: https://patreon.com/DillonWeldon?utm_medium=unknown&utm_source=join_link&utm_campaign=creatorshare_creator&utm_content=copyLinkJake Owen sits down with me for one of the most honest and wide-open conversations of his career. We talk Brooks & Dunn telling him to pump the brakes, Alan Jackson moments that shaped him, and why he’s doubling dow...

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 Cowb...

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 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 memo...

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 w...

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 indus...

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 hu...

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 in...

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...

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...

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:...

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 t...

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...

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...

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, subscr...

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 t...

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 m...

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 st...

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...

🎙️ 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...

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...