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!

There may be music from Keith Whitley that the world has never heard.In this powerful conversation, Jesse Keith Whitley opens up about his father’s legacy, the possibility of unreleased recordings, and what country fans have been wondering for decades.But this episode goes far beyond that.Jesse speaks candidly about growing up as the son of two country music icons, his relationship with Lorrie Morgan, his own journey through addiction and recent sobriety, and what it’s like carving out a career under one of the most legendary names in country music history. He also shares stories involving Sammy Kershaw, life on the road, finding his voice as an artist, and even the unexpected role cooking has played in his life.This is an honest, emotional, and revealing look at legacy, redemption, and the enduring impact of Keith Whitley on country music.If you’re a fan of classic country, outlaw stories, and untold music history, this is one you don’t want to miss!Keith Whitley unreleased music, unheard Keith Whitley songs, Jesse Keith Whitley interview, Keith Whitley lost recordings, Lorrie Morgan interview, country music podcast, classic country music stories, Sammy Kershaw story, country music legacy, Keith Whitley vault, outlaw country history, country music sobriety story, Jesse Keith Whitley sober, 90s country music, traditional country music, country music legends

Rodney Crowell was there.Before the myth. Before the legend. Before the Outlaw era became a T-shirt.In this episode of Drifting Cowboy, Rodney Crowell reflects on his time inside one of the most influential circles in country music history — alongside Johnny Cash, Guy Clark, Townes Van Zandt, Jerry Jeff Walker, Rosanne Cash, and the writers who shaped an entire generation.From the raw reality of the Outlaw movement to the deeply human moments behind the music, Rodney shares what it was really like in the rooms where these songs — and these legends — were born. We talk about songwriting, loyalty, Nashville in its wildest years, and the difference between the public image and the private truth.This isn’t nostalgia. It’s perspective from someone who lived it.If you care about country music history, the outlaw era, and the real stories behind the icons, this conversation is one you won’t forget.Subscribe for more deep dives into the legends, the lore, and the untold stories of country music.country music podcast, Rodney Crowell interview, Johnny Cash stories, Guy Clark stories, Townes Van Zandt interview, outlaw country era, Nashville songwriting history, Rosanne Cash, Jerry Jeff Walker, classic country music, country music history, Drifting Cowboy podcast, legendary songwriters, behind the scenes country music, outlaw movement Nashville, 1970s country music, Texas songwriters, country music legends, storytelling in country music

Rick Trevino was one of the defining voices of 90s country music. With major radio hits, national tours, and a presence during one of country’s biggest boom periods, he lived the life many artists dream about. But at the height of the era, something shifted.In this episode of Drifting Cowboy, Rick Trevino reflects on the rise of 90s country, the pressure of fame, navigating Nashville as a bilingual/Latino artist, and the pull that brought him back to his roots. He opens up about identity, industry expectations, touring during the golden era of country radio, and what it really felt like behind the spotlight.This is a thoughtful look at one of country music’s most transformative decades — and the personal crossroads that changed everything.If you love 90s country, classic Nashville stories, and honest conversations about fame, culture, and legacy, this one is for you.Subscribe for more in-depth country music interviews and untold stories from the artists who shaped the genre.rick trevino, rick trevino interview, 90s country music, 1990s country, latino country artist, bilingual country singer, nashville country music, drifiting cowboy podcast, country music podcast, country music history, los super seven, 90s country radio, 90s country stars, country music fame, country music industry, classic country interviews, country music legends, texas country music, hispanic country music, country music storytelling

Bobby Bare doesn’t just remember country music history — he helped shape it.In this rare, in-depth interview, Bobby Bare reflects on a career that places him at the center of country music’s most important moments. From his role in the early creative culture that helped influence the Fender Stratocaster, to discovering and supporting artists like Waylon Jennings and Billy Joe Shaver, to firsthand stories involving Johnny Cash, Tom T. Hall, and Chet Atkins, this conversation captures living history from one of the genre’s most influential figures.Bobby shares stories you don’t hear in documentaries or highlight reels — the behind-the-scenes moments, the creative risks, the personalities, and the decisions that quietly changed the course of country music. This isn’t a highlight package or a greatest-hits recap. It’s a firsthand account from someone who was there when modern country music was taking shape.If you care about country music’s roots, the people behind the legends, and how the genre truly evolved, this is a conversation worth preserving.Subscribe for more long-form interviews and deep dives into country music history, storytelling, and legacy.bobby bare, bobby bare interview, country music history, rare country music interview, waylon jennings, johnny cash, tom t hall, chet atkins, billy joe shaver, classic country music, outlaw country, nashville music history, music row nashville, country music legends, country music documentary, fender stratocaster history, guitar history, drifting cowboy podcast, country music podcast, classic country stories

Most people know Dan Seals as a country music legend — but before the hits on country radio, he was England Dan, one half of the massively successful duo England Dan & John Ford Coley.In this episode of the Drifting Cowboy Podcast, John Ford Coley sits down with me to tell the real story behind his partnership with Dan Seals, the rise of England Dan & John Ford Coley, and the honest, human reasons the duo ultimately broke up. John opens up about Dan’s transition into country music stardom, life after the split, and what it was really like navigating success at the height of the 1970s music industry.John also shares incredible firsthand stories from touring with Elton John, opening for Led Zeppelin, sharing stages with Three Dog Night, and how his career unexpectedly shifted into acting after the duo came to an end.This isn’t gossip or revisionist history — it’s reflection, perspective, and music history told by the man who lived it.If you’ve ever wondered why Dan Seals walked away from England Dan, or how one of the biggest soft-rock duos of the 1970s came to an end, this conversation finally fills in the blanks.Dan Seals, England Dan, John Ford Coley, England Dan and John Ford Coley, Dan Seals country music, Dan Seals England Dan, why Dan Seals left England Dan, Dan Seals breakup, John Ford Coley interview, Dan Seals story, country music history, classic country music, 70s soft rock, yacht rock stories, Elton John tour stories, Led Zeppelin opening act, Three Dog Night tour, country music podcast, music history podcast, Drifting Cowboy Podcast, country music interviews, classic hits behind the scenes, music legends interview, Dan Seals legacy

What really inspired “The Ride” — one of the most haunting songs in country music history?Songwriter Gary Gentry (“The Ride,” “The One I Loved Back Then,” and more) tells the unbelievable true story behind the song that has puzzled and fascinated fans for decades. After a night of heavy drinking, drugs, and reckless curiosity, Gary and a group of friends held a seance to provoke the spirit of Hank Williams.What happened next would stay with Gary forever.In this podcast, Gary recounts seeing what he believes was Hank Williams’ ghost — an encounter that later shaped the writing of “The Ride,” a song that feels less like fiction and more like a message passed down from country music’s past.This is not a rumor.This is not a legend told secondhand.This is the story straight from the songwriter himself.If you love:• Country music history• Nashville songwriting stories• Hank Williams folklore• Dark, strange, and unforgettable moments in music…this conversation is for you.Gary Gentry, The Ride song, Hank Williams ghost, Hank Williams seance, The Ride Gary Gentry, country music folklore, songwriting stories, Nashville songwriter, paranormal country music, haunted country music, Hank Williams legend, outlaw country history, The One I Loved Back Then, David Allan Coe songwriter, country music podcast, Drifting Cowboy podcast, strange country music stories, music history podcast, Hank Williams mystery, supernatural songwriting

In this powerful and intimate conversation, Georgette Jones opens up about what life was really like growing up as the daughter of two country music legends—George Jones and Tammy Wynette. Beyond the headlines, hit songs, and public struggles, Georgette shares personal stories, family memories, and behind-the-scenes moments that reveal who George and Tammy truly were when the lights were off and the world wasn’t watching.From childhood memories inside one of country music’s most famous families to honest reflections on love, fame, and legacy, this episode offers a rare, human look at two icons whose lives were as complicated as their music was timeless. This is not the tabloid version—it’s the truth, told by the person who lived it.If you care about country music history, real storytelling, and the people behind the legends, this is a conversation you don’t want to miss.George Jones, Tammy Wynette, Georgette Jones, George and Tammy, George Jones documentary, Tammy Wynette documentary, country music history, classic country music, outlaw country, country music legends, George Jones stories, Tammy Wynette stories, behind the music, country music podcast, Drifting Cowboy podcast, Nashville country music, real country stories, music legacy, country music family, country music interviews, classic country icons

Ray Benson of Asleep at the Wheel joins Drifting Cowboy for a deep-cut conversation about the people and moments that shaped country music history. Ray shares rare stories about his close friendships with Willie Nelson and Merle Haggard, including the time he watched Merle cuss out his label head Rick Blackburn. He talks about living in the same neighborhood as Townes Van Zandt and Blaze Foley, crossing paths with Stevie Ray Vaughan and Jimmie Vaughan before superstardom, and how Naomi Judd got the name Wynonna from Asleep at the Wheel—then legally renamed her daughter at 14 years old. This episode dives into outlaw country, Texas music, Americana, the Austin scene, Nashville politics, songwriting culture, and the unfiltered truth behind the legends. If you care about real country music stories, this is one you don’t skip.Willie Nelson podcast, Merle Haggard stories, Ray Benson interview, Asleep at the Wheel podcast, Townes Van Zandt stories, Blaze Foley stories, Stevie Ray Vaughan interview, Jimmie Vaughan stories, Naomi Judd Wynonna name origin, outlaw country history, Texas country music, Americana podcast, country music storytelling

Country songwriter Ward Davis joins Drifting Cowboy for a raw, no-filter conversation about his path through modern outlaw country — including the unbelievable moment Willie Nelson and Merle Haggard both recorded his song “Unfair Weather Friend.”Ward tells the full story behind how that song came together, what it meant to have two all-time legends cut the same song, and how that moment reshaped his career. He also talks about his longtime friendship with Cody Jinks, recording with Clint Black, and navigating success outside the Nashville system.Along the way, Ward shares a powerful story about meeting Kris Kristofferson and performing a show with him, offering rare insight into one of country music’s most respected icons.This episode is about songwriting, grit, loyalty, and the quiet moments that define a career — the parts most people never hear.If you care about real country music, the writers behind the songs, and the stories that live off the radio dial, this episode is for you.🎙️ Drifting Cowboy PodcastHosted by Dillon WeldonNew episodes featuring legendary artists, songwriters, and untold stories from country music history.Ward Davis, Ward Davis podcast, Ward Davis interview, Willie Nelson, Merle Haggard, Willie Nelson Merle Haggard song, Unfair Weather Friend, Kris Kristofferson, Ward Davis Kris Kristofferson, Cody Jinks, Ward Davis Cody Jinks, Clint Black, outlaw country, modern outlaw country, country songwriting, songwriter podcast, country music podcast, behind the songs country music, Texas country music, independent country artists, Drifting Cowboy podcast, Dillon Weldon, country music history, Nashville songwriting