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Drifting Cowboy

Author: Dillon Weldon

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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.
51 Episodes
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T. Graham Brown

T. Graham Brown

2024-12-2248:25

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!
TG Sheppard and Payton Dale

TG Sheppard and Payton Dale

2024-11-2601:14:15

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
Elizabeth Cook

Elizabeth Cook

2024-10-1152:25

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!
Bobby Braddock

Bobby Braddock

2024-08-0156:52

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

Gary Gentry

2024-05-2201:06:15

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

John Paycheck

2024-05-1549:34

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

Dale Watson

2024-01-0701:06:47

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!
Mickey Raphael

Mickey Raphael

2025-11-2040:43

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
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
Jake Owen

Jake Owen

2025-11-0648:51

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
Alex Miller

Alex Miller

2025-10-3151:33

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_linkFrom 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
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
Craig Campbell

Craig Campbell

2025-10-1646:00

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
Joe Nichols

Joe Nichols

2025-10-0901:15:07

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
Marcus King

Marcus King

2025-10-0244:52

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
Dusty Slay

Dusty Slay

2025-09-2501:00:21

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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