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Drifting Cowboy

Dillon Weldon
Drifting Cowboy
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  • Waylon Jennings' Band The Waylors
    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
    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
    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
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    51:33
  • Blackberry Smoke's Charlie Starr
    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
    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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About 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 every week.
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