This week on The Watering Hole, Rhett and Jager sit down with Texas singer-songwriter Ashton Naylor. Hailing from San Marcos, Texas, Ashton has quickly become one of the rising voices in the Red Dirt and Texas country scene, blending country, blues, Americana, and rock influences into a sound that's uniquely his own. Growing up on everything from Willie Nelson to Pearl Jam, Ashton shares the musical influences that shaped him, his journey into songwriting, and the road that led him from college student to full-time musician.

The conversation dives into the stories behind his debut record Foot in the Door, the challenges and rewards of independent artistry, life on the road, and what keeps him inspired as he continues to build his career. As always, expect plenty of laughs, great stories, and an honest look at the life of a working songwriter.

Check out Ashton Naylor and his music:

https://www.ashtonnaylormusic.com

Sponsors

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Co
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com

Follow The Watering Hole:

Instagram: @wateringholeofficial

Come for the music. Stay for the stories.

This week on The Watering Hole, Rhett and Jager sit down with Texas singer-songwriter Parker Ryan. Known for blending country storytelling with Southern rock energy, Parker shares the journey from his early days in Texas to building a growing fanbase across the Red Dirt and independent country scene. The conversation dives into songwriting, life on the road, musical influences, and the stories behind some of his most popular songs. Parker also talks about balancing authenticity with a growing career and what's next for him as he continues to carve out his own lane in country music.

As always, expect plenty of laughs, road stories, and the kind of honest conversation that makes The Watering Hole feel like pulling up a chair with old friends.

Follow Parker Ryan and check out his music:
https://www.parkerryanmusic.com

Sponsors

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Co
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com

Follow The Watering Hole:
Instagram: @wateringholeofficial

Come for the music. Stay for the stories.

This week on The Watering Hole, Rhett and Jager sit down with cowboy songster, storyteller, poet, and preservationist Andy Hedges. Andy has dedicated his career to keeping the traditions of cowboy music, poetry, and storytelling alive while introducing them to new audiences through his music and his podcast, Cowboy Crossroads.

The conversation dives into Andy's journey growing up in West Texas, his passion for collecting and preserving traditional cowboy songs, the stories behind some of his favorite pieces, and the importance of documenting the voices and history of the American West. They also discuss songwriting, folk traditions, life on the road, and how Andy has built a respected career centered around authentic storytelling.

Whether you're a fan of cowboy culture, folk music, history, or great storytelling, this episode is packed with fascinating conversations and unforgettable tales from the West.

Follow Andy Hedges and check out his music:
https://andyhedges.com

Sponsors

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Co.
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com

Follow The Watering Hole:
Instagram: https://www.instagram.com/wateringholeofficial

Come for the music. Stay for the stories.

This week at The Watering Hole, Rhett and Jager sit down with Texas country artist Kyle Garrett for a conversation about songwriting, chasing the music dream, life on the road, and the stories that inspire his songs. Kyle shares his journey through the Texas music scene, the lessons he's learned along the way, and what continues to drive him as an artist. From heartfelt songwriting to behind-the-scenes road stories, this episode is packed with great conversation and plenty of laughs.

If you're a fan of authentic country music and the artists keeping the tradition alive while carving their own path, you won't want to miss this one.

Follow Kyle Garrett and check out his music:
https://kylegarrettmusic.com

Sponsors

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Co.
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com

Follow The Watering Hole:
Instagram: https://www.instagram.com/wateringholeofficial

Come for the music. Stay for the stories.

Jeff Crosby Joins The Watering Hole

This week, Rhett and Jager sit down with singer-songwriter Jeff Crosby for a conversation filled with stories from the road, the songwriting process, and the experiences that have shaped his career. Jeff shares how growing up in Idaho influenced his music, the evolution of his sound, and the lessons he's learned from years of touring and creating authentic, roots-driven songs.

From life on the highway to the inspiration behind his music, this episode offers an honest look at the journey of an independent artist who continues to connect with audiences through heartfelt storytelling and memorable songs.

Check out Jeff Crosby:
https://jeffcrosbymusic.com

Sponsors

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Company
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

This week on the podcast, we're joined by Charlie Starr, the lead singer, songwriter, and guitarist of Blackberry Smoke. Charlie sits down with us to talk about the band's journey from playing small clubs to becoming one of the most respected names in Southern rock and Americana music. We dive into songwriting, life on the road, the influence of classic Southern music, and what continues to inspire Blackberry Smoke after all these years.

From stories behind some of the band's biggest songs to insights into their loyal fanbase and enduring success, this is a conversation music fans won't want to miss.

Follow Charlie and Blackberry Smoke:
https://www.blackberrysmoke.com

Presented by:

Deep Eddy Vodka
https://deepeddyvodka.com

Double B Hat Co.
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

This week on the podcast, we sit down with Hope MacGregor for a powerful conversation about music, resilience, and the unexpected paths that lead us back to our purpose.

Hope’s story is anything but ordinary—she went from growing up in the Midwest with a love for singing and songwriting, to serving as a U.S. Army helicopter pilot after graduating from West Point. Life took another turn when she transitioned out of the military, attended law school, and then found herself in the middle of personal loss and major life change. In that season, an old guitar resurfaced—and with it, a return to writing music that was honest, healing, and deeply personal.

Today, Hope is carving out her place in the country and Americana scene with songs that blend heartbreak, humor, and hard-earned wisdom. We talk about her journey from the cockpit to the courtroom to the stage, the stories behind her music, and how she turned some of life’s hardest moments into art that connects with people everywhere.

Follow Hope MacGregor:
https://www.hopemacgregormusic.com

Episode Sponsors:
Double B Hat Co.
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Deep Eddy Vodka
https://deepeddyvodka.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com

🎙️ Tune in for an inspiring conversation with Hope MacGregor and her journey through music, service, and self-discovery.

#HopeMacGregor #TexasMusic #Americana #CountryMusic #Podcast #SingerSongwriter #LiveMusic #Storytelling #WomenInMusic

This week on the podcast, we sit down with Cory Morrow for a conversation packed with stories, songwriting, and life on the road. Cory shares the journey behind his career, the highs and lows of the music business, and what continues to inspire him after decades of performing for fans across Texas and beyond.

From the early days of the Red Dirt and Texas Country movement to building a loyal fanbase through authentic songwriting and relentless touring, Cory opens up about the experiences that have shaped both his music and his life. We talk about the songs that connected with audiences, the evolution of the Texas music scene, and what's next for one of the genre's most respected artists.

Whether you're a longtime fan or just discovering his music, this episode is filled with great stories, plenty of laughs, and an inside look at the career of a true Texas music icon.

Follow Cory Morrow:
https://corymorrow.com

Episode Sponsors:
Double B Hat Co.
https://doublebhatcompany.com

CH Lonestar Promo
https://chlonestarpromo.com

Deep Eddy Vodka
https://deepeddyvodka.com

Iron Monk Brewing Company
https://ironmonkbeer.com

Certified Hustler
https://thecertifiedhustler.com

Stilly Vintage
https://stillyvintage.com