Drifting Cowboy

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!

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

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!

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 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 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 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!

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

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

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

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

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.

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

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 BuffettMac’s Southern childhood and musical rootsStories about John Prine and Toby KeithSongwriting 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