Happy Hour with Deb

Get ready for a little country music, real-life stories, and plenty of heart! 

On this episode of Happy Hour with Deb, host Deb Cherella sits down with rising country artist Trey Calloway to talk about his journey into country music, the family that helped shape him, his upcoming songs, and what keeps him chasing his dreams.

Originally from North Carolina and now based in Nashville, Trey started singing in church and was already a seasoned performer by the age of ten. While southern and contemporary gospel were his first musical loves, he eventually discovered a passion for the rocking, boot-stomping storytelling of ’90s country legends. That sound continues to influence his music today.

Trey has shared the stage with country favorites including Joe Diffie, Tracy Lawrence, McBride & The Ride, Pat Green, Edwin McCain, and Craig Campbell. His hard work is paying off, too! Since mid-2023, he has won Songwriter of the Year at the Texas Country Music Awards, had a music video featured on CMT, landed on Spotify editorial playlists, and earned more than three million streams on Spotify alone. 
Support the show
Happy Hour with Deb
Real Talk. Big Feelings. Country Soul.
New episodes weekly — available on Spotify, Apple Podcasts & YouTube
 🔗 Follow us everywhere: @happyhourwithdeb
 📬 For guest inquiries or collaborations: happyhourwithdeb@gmail.com

What happens when heartbreak becomes music, pain becomes a lesson, and you find the strength to move forward? 

On this episode of Happy Hour with Deb, country and Soulful Americana powerhouse Morgan Myles joins Deb for a deeply personal conversation about the stories behind her music, the experiences that shaped her, and the future she's building for herself.

Morgan opens up about her powerful album, "Laced", a 12-song collection exploring love, loss, reflection, connection, and self-empowerment. She shares the heartbreaking story behind the title track and how she navigated the complexities of a toxic relationship, turning difficult experiences into music that connects with people on a deeper level.

We also revisit her unforgettable journey on NBC's *The Voice* in 2022, where she competed on Team Camila Cabello and captured the attention of millions with her incredible vocals and undeniable stage presence.

And that's not all! Morgan talks about her plans for the next five years, what she's working toward in her career, and what it takes to keep moving forward while staying true to yourself. 
Support the show
Happy Hour with Deb
Real Talk. Big Feelings. Country Soul.
New episodes weekly — available on Spotify, Apple Podcasts & YouTube
 🔗 Follow us everywhere: @happyhourwithdeb
 📬 For guest inquiries or collaborations: happyhourwithdeb@gmail.com

A Texas-born country artist, Opry performer, CMT Next Women of Country alum, and Thirty Tigers artist, Kimberly Kelly has built her career around sharp songwriting, classic country charm, humor, and plenty of honky-tonk soul.
In this conversation, Kimberly opens up about how her country music journey began, growing up in Texas, finding her place in the country music world, and what it means to balance life as an artist with being a wife and mother.
We also talk about her music, her 2025 hit “Modern Day Woman,” her upcoming 2026 full-length album, her hilarious new release “Stripper for a Week,” upcoming shows, and what’s ahead for her career.
Kimberly has collaborated with country legends and powerhouse writers, including Steve Wariner and Kix Brooks, while her husband, hit songwriter and producer Brett Tyler, brings his own impressive songwriting history to their country music power-couple story. Brett’s credits include “Dandelion” by Ella Langley, “Man Made a Bar” by Morgan Wallen & Eric Church, “I Know a Guy” by Chris Young, and many more.
From Texas honky-tonks to the Grand Ole Opry and beyond, Kimberly Kelly is proving that being a “Modern Day Woman” can still come with plenty of country heart, humor, and tradition. 
Support the show
Happy Hour with Deb
Real Talk. Big Feelings. Country Soul.
New episodes weekly — available on Spotify, Apple Podcasts & YouTube
 🔗 Follow us everywhere: @happyhourwithdeb
 📬 For guest inquiries or collaborations: happyhourwithdeb@gmail.com

Chandler Flint is back on Happy Hour with Deb! 

We first met Chandler before, but this time we caught up with her at CRS in Nashville and got to go a little deeper.

We talked about what’s coming next in her music, what she’s been working on, and what fans can look forward to. But this conversation also took a more personal turn as Chandler opened up about relationships, life, growth, and the experiences that shape who we are beyond the music.

It’s always different when you sit down with someone for a second time. You get past the surface and have the chance to really talk.

Join Deb and Chandler for an honest, fun, and personal conversation about music, relationships, what’s next, and everything in between. 
Support the show
Happy Hour with Deb
Real Talk. Big Feelings. Country Soul.
New episodes weekly — available on Spotify, Apple Podcasts & YouTube
 🔗 Follow us everywhere: @happyhourwithdeb
 📬 For guest inquiries or collaborations: happyhourwithdeb@gmail.com

What happens when you walk away from the music industry at the height of your career, build a life centered around family, and years later realize that the music is still calling?

On this episode of Happy Hour with Deb, Deb sits down with country music artist and songwriter Cyndi Thomson for a deeply personal conversation about her incredible journey back to music.

Cyndi first made her mark in country music with her debut album My World and the chart-topping hit “What I Really Meant to Say.” After experiencing the intensity and demands that came with her early success, Cyndi made the difficult decision to step away from the industry.

What followed was a completely different chapter of life. Cyndi became a mother, built a family, launched her jewelry company Haybelle Co., and found a new appreciation for the life happening outside of the spotlight.

Now, Cyndi is back.

In this conversation, she opens up about what it really felt like to return to Nashville and the music industry after so many years away, what changed during her time away, and what it means to come back with a completely different perspective.

Deb and Cyndi also talk about motherhood, being present, not rushing through life, and remembering to enjoy the moments along the way. Cyndi’s recent collaboration with Vince Gill on “Eighteen Summers” touches on that same idea of how quickly the years of raising children can pass, making this chapter of her story even more meaningful.

Cyndi’s comeback has included heartfelt new music such as “The Georgia In Me,” “Liar,” “Acres of Diamonds,” and “Five More Minutes,” with her new music reflecting the experiences, relationships, and perspective she gained during her years away. Her official website describes Acres of Diamonds as a new chapter with deeper songs, a stronger voice, and more compelling storytelling.

This isn't just a conversation about making a comeback.

It's about knowing when to step away, knowing when it's time to come back, and learning to appreciate the life you're living while you're living it. 
Support the show
Happy Hour with Deb
Real Talk. Big Feelings. Country Soul.
New episodes weekly — available on Spotify, Apple Podcasts & YouTube
 🔗 Follow us everywhere: @happyhourwithdeb
 📬 For guest inquiries or collaborations: happyhourwithdeb@gmail.com