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PODCAST

Drifting Cowboy

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

music music interviews

All Episodes

00:32:46

Chandler Walters

Drifting Cowboy ·

2025/05/06

In this episode of the Drifting Cowboy Podcast, rising country artist Chandler Walters joins the show to talk about the wild ride he’s on—opening for Post Malone this summer and signing with Ernest’s new label, DeVille Records. But beyond the headlines, Chandler is doing something rare in today’s country music scene: he’s bringing back Western swing in a big way, blending tradition with fresh energy and style.We dive into how he got here, what it’s like working with major names in the industry, and

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02:11:18

Travis Tritt

Drifting Cowboy ·

2025/04/29

🎙️ Country legend Travis Tritt joins Dillon Weldon on the Drifting Cowboy Podcast for a powerful and unfiltered conversation about music, fame, family, and staying true to your roots. In this exclusive full-length interview, Tritt opens up about his outlaw image, his biggest hits, working with legends, and what he thinks about the state of country music today.Whether you're a longtime Travis Tritt fan or just love real country music stories, this episode is packed with behind-the-scenes moments,

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00:47:52

Don Goodman

Drifting Cowboy ·

2025/04/16

In this episode of the Drifting Cowboy Podcast, legendary songwriter Don Goodman takes us on a journey through his incredible career—writing songs that have saved lives, shaped country music, and stood the test of time. From penning timeless hits like Angels Among Us to co-writing Ol’ Red, Goodman shares powerful stories from behind the scenes in Nashville, including a wild moment involving Janis Joplin, a run-in with the law, and how a jail sentence became inspiration for one of country music’s

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00:46:03

Grayson Russell

Drifting Cowboy ·

2025/04/12

🎙️ On this episode of The Drifting Cowboy podcast, Dillon Weldon sits down with actor and country artist Grayson Russell—his close friend and one of Nashville’s rising stars. You know Grayson from his unforgettable roles in Talladega Nights: The Ballad of Ricky Bobby, the Diary of a Wimpy Kid series, and starring alongside Tom Hanks in the World War II drama Greyhound.In this exclusive conversation, Dillon and Grayson dive into everything from Hollywood behind-the-scenes stories to Grayson’s

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00:14:34

Ian Flanigan

Drifting Cowboy ·

2025/04/11

About This EpisodeIn this episode of Drifting Cowboy, Dillon Weldon sits down with powerhouse vocalist and The Voice finalist Ian Flanigan for an in-depth conversation about life, music, and staying grounded while chasing big dreams. Known for his gravel-rich voice and soulful songwriting, Ian shares how his time on The Voice changed his life—and how he's stayed true to his sound ever since.We talk about his journey from playing bar gigs to performing on national television, working with Blake

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00:08:11

Billie Jo Jones

Drifting Cowboy ·

2025/04/10

About This EpisodeOn this episode of Drifting Cowboy, Dillon Weldon welcomes country singer and songwriter Billie Jo Jones, whose honest lyrics and throwback sound are turning heads across the country music scene. Billie Jo shares her journey from small-town beginnings to becoming one of the freshest voices in traditional country, all while staying true to her roots.We dig into her songwriting process, her biggest musical influences, and what it's like being an independent artist carving her own

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00:17:54

Makenzie Phipps

Drifting Cowboy ·

2025/04/09

About This EpisodeIn this special episode of Drifting Cowboy, Dillon Weldon sits down with rising country music star Makenzie Phipps for a heartfelt and revealing conversation. Known for her traditional country sound and powerful vocals, Makenzie opens up about her journey in the music industry, the stories behind her songs, her Appalachian roots, and what it takes to make it in Nashville today.We talk about everything from her viral performances and love for classic country to the challenges facing

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00:29:27

The Malpass Brothers

Drifting Cowboy ·

2025/04/06

Step back in time with The Malpass Brothers on the Drifting Cowboy podcast! In this episode, Dillon Weldon sits down with the traditional country music duo keeping the spirit of classic country alive. From their musical roots and influences like Merle Haggard and Johnny Cash, to their hilarious stories from the road and life behind the scenes, this conversation is full of heart, humor, and honky-tonk soul.Whether you're a fan of old-school country, bluegrass, or just love great storytelling,

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00:10:19

Moe Bandy

Drifting Cowboy ·

2025/04/03

In this episode, I sit down with country music legend and the King of Cheating Songs, Moe Bandy. We talk about his friendships with folks like Joe Stampley and Lefty Frizzell, his hits like Bandy the Rodeo Clown and Just Good Ol' Boys and campaigning for the Bushes. Enjoy!

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00:27:34

Trey Calloway

Drifting Cowboy ·

2025/03/31

In this episode, I sit down with Trey Calloway. Trey is a new artist who is making his way in the traditional country scene. Be sure to check out his music and I hope you enjoy the conversation!

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00:45:38

Randy Travis, Mary Travis and Kyle Lehning

Drifting Cowboy ·

2025/03/29

In this episode, I had the honor of talking with country music legend Randy Travis, his wife Mary Travis, and his career producer Kyle Lehning. We talked about everything from Storms of Life to Randy's acting career, AI, James Dupre and so much more. Enjoy!

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01:11:00

Dickey Lee

Drifting Cowboy ·

2025/03/27

In this episode, I sit down with music legend, Dickey Lee. Dickey has been in for longer then ... well, maybe anyone still living. He signed with the famous Sun Records all the way back in 1957 and went on to have a great career as an artist with songs like Patches and Laurie, and he is also a Hall of Fame songwriter, writing hits like She Thinks I Still Care, Let's Fall to Pieces Together, Keeper of the Stars and many more. Enjoy!

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00:28:20

Duane Allen of The Oak Ridge Boys

Drifting Cowboy ·

2025/03/25

In this episode, I sit down with legendary Oak Ridge Boy Duane Allen. Duane walks us through the colorful history of The Oak Ridge Boys, talks about touring with folks like Ernest Tubb and talks about how the band operates. Enjoy!

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00:35:19

Kelly Lang

Drifting Cowboy ·

2025/03/22

In this episode, I sat down with Kelly Lang and we talked about her childhood touring with Conway Twitty, her battle with breast cancer, Ralph Emory and much more. Enjoy!

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01:40:43

Benjamin Tod

Drifting Cowboy ·

2025/03/19

In this episode, I sat down with Ben Tod and we talked about everything... and I do mean everything! From Dallas Frasier to fixing leaking roofs, this was a fun conversation. Enjoy!

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00:53:56

Mark Wills

Drifting Cowboy ·

2025/03/16

In this episode, I sit down with 90s Country star Mark Wills. Mark had hits like Don't Laugh At Me, 19 Something, Jacob's Ladder and many more. We talk about everything from his career to the Opry. Enjoy!

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00:54:11

Tristan Tritt

Drifting Cowboy ·

2025/03/06

In this episode, I sit down with Tristan Tritt. Tristan has grown up in the country music industry with his father, Travis Tritt. We talk about his music career, Nashville, authenticity and so much more. Enjoy!

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00:48:25

T. Graham Brown

Drifting Cowboy ·

2024/12/22

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!

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01:14:15

TG Sheppard and Payton Dale

Drifting Cowboy ·

2024/11/26

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

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00:52:25

Elizabeth Cook

Drifting Cowboy ·

2024/10/11

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!

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48 results

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