Code Red Talk: The Stories Behind Country Music with Dylan Weldon (The Drifting Cowboy Podcast)

️ Code Red Talk: The Stories Behind Country Music with Dylan Weldon (The Drifting Cowboy Podcast)

 

In this powerful episode of Code Red Talk, Zach Terry sits down with Dylan Weldon, host of The Drifting Cowboy Podcast — one of the most compelling voices in today’s traditional country revival.

From Waylon Jennings and Merle Haggard to Willie Nelson and Sturgill Simpson, Dylan shares the untold stories, surprising legacies, and hard-won lessons that shaped the sound of American grit.

 

DILLON WELDON BIO: Dillon is from the small, rural town of Sugartown in southwest Louisiana, population 176. He has loved country music as long as he can remember. When he was 3 years old, he asked for a Sony Walkman and a Johnny PayCheck’s Greatest Hits cassette for Christmas. He has always been fascinated with the history of country music, its artists, songwriters and the stories behind the songs. Dillon now lives in Nashville and has made a career out of his passion for country music history, through his social media platform and the Drifting Cowboy podcast where he has sat down with legends such as Jamey Johnson, Travis Tritt, Bobby Braddock, Randy Travis and many more. Dillon believes that the history of country music is as important as the music itself and should be kept alive.

 

Expect deep insight, a few laughs, and a front-row seat to the intersection of faith, culture, and country music — told by two men who live it.

 

️ Timestamps

00:00 – Dylan’s honest prayer before his TikTok breakthrough

01:10 – The Hank Jr. video that changed everything

01:37 – Welcome to Code Red Talk — Zach introduces Dylan Weldon

03:10 – How Dylan built a songwriting community during lockdown

05:05 – The story behind the yellow cap and smart personal branding

06:17 – Branding lessons from Bear Bryant, Waylon, and Lincoln

07:28 – Waylon Jennings’ estate, legacy, and influence

08:55 – Growing up in rhythm: Merle Haggard and family memories

10:10 – Elvis Presley’s estate and the business of legacy management

12:23 – Why preserving musical history matters for future generations

14:09 – Finding forgotten legends like Sonny Throckmorton

15:10 – Johnny Cash & Kris Kristofferson: stories of boldness and friendship

18:00 – Merle Kilgore, “Ring of Fire,” and the deal of a lifetime

20:00 – Jimmy Buffett’s secret business discipline

21:02 – How bad accountants ruined country icons

22:21 – Shooter Jennings and the unreleased Waylon tapes

24:12 – Inside the Songbird album and possible duets to come

27:05 – Willie Nelson’s jazz influence and Django Reinhardt connection

30:20 – What makes country music truly “country”

33:10 – Why “bro country” misses the mark

36:00 – Jesco White and the roots of Appalachian folk dance

38:20 – Dwight Yoakam, Buck Owens, and the Bakersfield sound

40:10 – Hee Haw nostalgia and the decline of TV country shows

41:00 – YouTube beats Netflix: people crave real conversation

43:00 – Why AM radio still holds power for talk and truth

46:05 – How social media changed the path to success in Nashville

48:45 – Advice for young artists: never sign without a good lawyer

50:20 – Record labels that sign artists just to shelve them