Drifting Cowboy

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Rating
4.8
from
44 reviews
This podcast has
60 episodes
Language
Publisher
Explicit
No
Date created
2025/05/11
Latest episode
2026/02/05
Average duration
59 min.
Release period
9 days

Description

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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Bobby Bare
2026/02/05
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
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John Ford Coley
2026/01/22
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
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Gary Gentry
2026/01/15
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
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Georgette Jones
2026/01/01
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
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Ray Benson
2025/12/24
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
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Ward Davis
2025/12/18
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
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Jeannie C. Riley
2025/12/11
Country music icon Jeannie C. Riley sits down for a rare, wide-open conversation about her life, her career, and the stories behind “Harper Valley PTA.” She shares unforgettable moments with Tom T. Hall, Charlie Daniels, and other Nashville legends, while reflecting on the highs, the heartbreak, and what she really lived through in the industry.This is Jeannie C. Riley like you’ve never seen her — honest, sharp, funny, and full of wisdom from a lifetime in country music. If you love classic country, storytelling, or behind-the-scenes history, this two-hour interview is a treasure.jeannie c riley, jeannie c riley interview, harper valley pta, tom t hall, charlie daniels, drifting cowboy podcast, country music history, classic country stories, harper valley pta story, jeannie c riley podcast, nashville legends, 60s country music, female country artists, country music interviews, jeannie c riley untold story, harper valley pta songwriter, tom t hall stories, charlie daniels stories, country music women, jeannie c riley 2025
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Whisperin’ Bill Anderson
2025/12/04
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 Family Reunion, his early days on television game shows and soap operas, and what it truly means to stay relevant in country music for over six decades. 🎧 Full of laughter, wisdom, and never-before-told stories from a Hall of Fame songwriter. 👉 Watch the full interview and subscribe for more conversations with the legends who built country music. Bill Anderson, Whisperin Bill Anderson, Roger Miller, Faron Young, Whiskey Lullaby, Give It Away, Country Family Reunion, Grand Ole Opry, Country Music Hall of Fame, Nashville, Country Music History, Country Legends, Songwriting, Country Songwriter Stories, Drifting Cowboy Podcast, Dillon Weldon, Country Interviews, Behind the Songs, Country Music Icons, Country Music Stories, Traditional Country, 90s Country, Classic Country, Bill Anderson Interview, Bill Anderson Podcast, Country Storytellers, Country Music Hall of Famer
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Bernie Leadon (Founding Member of The Eagles)
2025/11/27
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 chemistry, why he left, and what it was like returning decades later for the History of the Eagles tour. Bernie also opens up about Gram’s death, the California country-rock scene, and the new music he’s creating today. If you love the Eagles, Gram Parsons, real music history, or the roots of country rock, this episode is packed with stories you won’t hear anywhere else.bernie leadon, eagles founding member, the eagles, gram parsons, flying burrito brothers, altamont speedway, witchy woman, eagles interview, gram parsons stories, bernie leadon interview, drifting cowboy podcast, dillon weldon, country rock history, classic rock stories, music history podcast, history of the eagles, california country rock, american music history, gram parsons death, eagles founding story, bernie leadon new music, eagles documentary, country music podcast, rock and roll history
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Mickey Raphael
2025/11/20
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 music he’s working on now. This episode is a front-row seat to country music history from a man who lived it, breathed it, and shaped it beside one of the greatest of all time.mickey raphael, willie nelson, hells angels, hells angels story, mickey raphael interview, willie nelson band, guy clark, townes van zandt, outlaw country stories, country music podcast, drifting cowboy podcast, harmonica player, willie nelson road stories, country music legends, country music history, nashville podcast, dillon weldon, country music interview, willie nelson stories, mickey raphael harmonica, country road stories
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Waylon Jennings' Band The Waylors
2025/11/13
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 road with the Outlaw himself.They share what it was really like working for Waylon, the pranks they pulled on him, how Big Bird actually caught on fire, behind-the-scenes moments from The Dukes of Hazzard, and memories of Buddy Holly and The Crickets, Nashville in the ’60s and ’70s, and the rise of the Outlaw movement.This episode is pure country music history straight from the men who lived it. If you love Waylon Jennings, classic country, or behind-the-scenes stories that feel like opening a hidden vault, this is one you won’t forget.waylon jennings, waylon jennings interview, waylon jennings band, outlaw country, outlaw country stories, buddy holly stories, dukes of hazzard, country music history, waylon jennings podcast, waylon jennings documentary, waymore’s blues band, dillon weldon drifting cowboy, big bird on fire story, classic country stories, nashville history, country music legends, untold outlaw stories, jennings family, honky tonk history, waylon jennings 2025, drifting cowboy podcast
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Jake Owen
2025/11/06
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 down on real country music. Jake also opens up about working with Shooter Jennings on his new album and the shift toward a raw, traditional sound.From his early days grinding in bars to becoming one of the biggest names of the 2000s and 2010s, Jake walks through the highs, lows, left turns, and lessons learned along the way. If you love stories about Brooks & Dunn, Alan Jackson, Hank Jr., traditional country, songwriting, and the evolution of Nashville—this episode is loaded.In this episode:The moment Brooks & Dunn told Jake Owen to STOPJake’s memories of Alan Jackson and the old-school Nashville wayHis deep love for Hank Jr. and classic countryHow working with Shooter Jennings changed his soundWhy his new album leans heavy into traditional country musicStories from throughout Jake’s career—touring, radio, writing, and the moments that shaped his voiceIf you want to see where country music is going—and where it came from—this conversation is a perfect snapshot.Jake Owen, Jake Owen interview, Jake Owen podcast, Jake Owen new album, Shooter Jennings, Shooter Jennings Jake Owen, Brooks and Dunn, Brooks & Dunn, Alan Jackson, Hank Jr., Hank Williams Jr., traditional country, traditional country music, country music podcast, Drifting Cowboy podcast, Dillon Weldon, country music interviews, Nashville stories, country music history, Jake Owen Shooter Jennings, Jake Owen Brooks and Dunn story, Jake Owen Alan Jackson story, 2000s country music, country music storytelling, Jake Owen 2025
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Alex Miller
2025/10/31
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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Blackberry Smoke's Charlie Starr
2025/10/23
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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Craig Campbell
2025/10/16
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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4.8 out of 5
44 reviews
kristerz 2025/12/17
New around these parts
I grew up surrounded by classic country and Tejano music. It wasn’t until I was an adult. I really fell in love with the genre and started to apprecia...
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ruralroutemomma 2025/12/16
Great podcast
What a wonderful podcast to listen to! I’m so glad I found this channel. Thank you Dillon
JohnCzech23 2025/12/09
Dillon is a great host
Awesome guests, great stories, love this pod!
Oaks68 2025/10/20
Thank You
Dillion I just came across your podcast, wow, Duane Allen first and then William Lee Golden, ( Oaks fan since first concert in 1968, at age 10) liste...
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Glen in Kokomo 2025/08/24
Love the show!
Just discovered this podcast. Great guests, inside stories, down home feel…love it all!!
Blkh9878 2025/08/14
Great pod about real country music
10/10 thank you for what you are doing !!!!!!
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