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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

00:17:54

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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00:56:52

Bobby Braddock

Drifting Cowboy ·

2024/08/01

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.

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01:06:15

Gary Gentry

Drifting Cowboy ·

2024/05/22

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.

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00:49:34

John Paycheck

Drifting Cowboy ·

2024/05/15

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.

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01:06:47

Dale Watson

Drifting Cowboy ·

2024/01/07

Dale Watson is the founder of the Ameripolitan music genre as well as the Ameripolitan music awards.www.ameripolitan.org

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00:54:52

Haunted Country Music with Dillan Holliday

Drifting Cowboy ·

2023/10/31

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.

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00:18:10

The Life and Times of Townes Van Zandt

Drifting Cowboy ·

2023/09/11

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.

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82 results

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