Country artist JD Shelburne is back to talk about his latest album Raised on the Good Stuff, his Kentucky roots, and the journey that’s taken him from small-town stages to the Opry. JD reflects on growing up in Taylorsville, performing in church, and teaching himself guitar after a life-changing moment in his grandmother’s house that sparked his passion for music. He shares stories from his early days chasing a dream in Nashville, playing more than 3,000 shows, and building an independent career driven by relentless work ethic and strong fan connection.

JD dives into collaborating with songwriter Mark Nesler and recording with legends like the Oak Ridge Boys and Crystal Gayle. He also talks about his partnership with Inclusion Bourbon, the nerves and excitement of making his debut at the Grand Ole Opry, memorable onstage mishaps, and what fans can expect from him in 2026.

Jonathan’s Drinking: Bardstown Bourbon Bottled-in-Bond

Country singer-songwriter MaRynn Taylor joins Bar Conversations to talk about her journey from growing up in Michigan to releasing her self-titled debut album. MaRynn shares how performing for her family at just four years old with a plastic microphone sparked her love for music, the artists who influenced her early on, and how small-town life shaped both her songwriting and identity. She reflects on visiting Nashville at age 12, moving there at 17, and missing out on traditional high school milestones in order to chase her dream in Music City.

MaRynn also opens up about her breakthrough moments, including signing her record and publishing deals live on air, making her Grand Ole Opry debut, and opening for Kelsea Ballerini on her arena tour. We dive into the making of her self-titled album, why it felt like the right time to introduce herself so personally, and the stories behind songs like Small Town Spinnin’, Season 2 of Friends, Dirty Blonde, and She Broke Up With The Boy. Plus, she talks about the importance of connecting with fans, trading friendship bracelets, performing in meaningful hometown venues, and what fans can expect from her in 2026.

Jonathan’s Drinking: Joseph Magnus Triple Cask Sherry & Cognac

Country artist Hayden Baker talks about his journey from growing up in Katy, Texas, to becoming one of the most respected guitar players in modern country music. Hayden shares how early exposure to rural life, sports, and faith shaped who he is, and how picking up a guitar at 16—something he’s called a “God thing”—changed the direction of his life. He reflects on how an unexpected college injury led him to singing and songwriting, the music that influenced him early on, and what it’s like to have Brad Paisley call him his “new favorite guitarist.”

Hayden also dives into his new album Alive & Well, explaining why he intentionally shifted the focus from guitar flash to growth as a vocalist and storyteller. He talks about working with Brad Paisley and Ronnie Dunn, receiving a gifted 1953 Telecaster, and the story behind Brad’s guest solo on Don’t Meet Your Heroes. We also discuss his decade-long independent career, winning Musician of the Year at the Texas Country Music Industry Awards, standout tracks like Home Into a House, I Had a Headache Once, and Country Ain’t Goin’ Nowhere, and what fans can expect from Hayden in 2026.

Jonathan’s Drinking: Still Austin Cask Strength Bourbon

Country artist Olivia Harms talks about her journey from growing up on a multi-generation cattle ranch in Oregon to appearing on the CBS series The Road. Olivia shares how being raised in a musical family—literally taking the stage at just two days old—set her on a path toward country music, along with the early influences that shaped her sound. She reflects on recording her first album at 16, navigating a more pop-country phase, and ultimately finding her voice.

Additionally, Olivia opens up about being hand-selected by Taylor Sheridan and Blake Shelton for The Road, competing and opening for Keith Urban, and what the experience taught her about herself as an artist. We also dive into her songwriting process, including the stories behind Hey There Cowboy, Kiddie Pool, and This Ain’t My First Rodeo, as well as her 2025 releases Sent from Above and I’m On My Way. Plus, she talks about balancing life on a working cattle ranch with playing more than 200 shows a year, what she loves most about being on stage, and what fans can expect from Olivia Harms in 2026.

Jonathan’s Drinking: Sagamore High Rye Bourbon

Maygen & The Birdwatcher join Bar Conversations to talk about their latest album The Americana Dream, songwriting, and building a band rooted in collaboration. We chat with Maygen Lacey and Noah Neumann to discuss growing up in Minnesota, early musical influences, and how their partnership began. From overcoming a fear of performing live to breaking the rules in piano lessons, they share how writing together helped shape their sound and confidence, as well as the origin of the band’s name and their evolution from a duo into a full six-piece band.

Maygen and Noah also dive into The Americana Dream, described as a “sonic travelogue,” and what it was like working with producer John Fields, who pushed them to trust their instincts in the studio. They talk about balancing music with family and full-time careers, the early success of Moonshine and Bootleggin’ At The Flower Shoppe, and why collaboration remains central to everything they do. Plus, they share favorite songs to perform live and what fans can expect in 2026.

Jonathan’s Drinking: Chicken Cock Ryeteous Blonde

Singer-songwriter Alexandra King shares the story behind her debut EP Across the Pond, blending her New York upbringing with her deep Irish roots. Alexandra talks about growing up surrounded by music, from parents who met through music to having a piano before she was even born, and how summers spent on her aunt’s sheep farm in Ireland shaped her identity and songwriting. She reflects on studying abroad in Galway, nearly becoming a lawyer, and ultimately following her calling to Nashville. Alexandra discusses surviving a life-altering spinal cord injury in 2020, how doctors initially questioned whether she’d ever regain movement, and how music became a vital part of her recovery. We dive into the making of Across the Pond, including original tracks like Freckles (In An Old Pub) and Lose Me to Dublin, as well as her decision to include traditional covers Galway Girl and Willie McBride. Plus, she shares stories about her deaf dog Pillsbury, favorite songs to perform live, and what fans can expect from her in 2026.Jonathan’s Drinking: Wheel Horse x Narragansett Baltic Porter Beer Barrel Finish Whiskey

Bluegrass-folk trio Damn Tall Buildings released their latest album The Universe Is Hungry this fall. We sit down with Avery Ballotta to talk about growing up in Montana, early musical influences, and how a love for music—and the fiddle—started at a young age. We dive deep into the inspiration behind the album, recording process, and the band’s commitment to staying truly independent—self-producing, self-managing, and even running their own music school in Brooklyn.

Avery shares stories from studying at Berklee College of Music, meeting bandmates Max Capistran and Sasha Dubyk, and how the group’s journey began with busking on the streets of Boston before evolving into a decade-long partnership rooted in friendship, craftsmanship, and creative freedom. He also talks about touring with the U.S. State Department, performing bluegrass during cultural exchanges in Ethiopia and Saudi Arabia, and reimagining Roy Orbison’s “Blue Bayou” through a bluegrass lens.

Plus, we discuss the band’s one-microphone live setup, how they decide vocal leads without a frontman, favorite songs to perform on stage, unforgettable moments from 2025, and what fans can expect from Damn Tall Buildings in 2026.

Jonathan’s Drinking: McKenzie Straight Bourbon Whiskey

Country singer-songwriter Jeremy Pinnell talks about his new album Decades, life growing up in Northern Kentucky, and the influences that shaped his music.

From a childhood filled with Christian hymns and classic rock legends to the life-changing moment of seeing Guns N’ Roses’ “Welcome to the Jungle,” Jeremy shares how punk rock energy evolved into his heartfelt country sound. He opens up about his songwriting process, drawing from personal experience while crafting stories that resonate, and reflects on the journey from his first album OH/KY to his latest work, exploring themes of love, loss, and the modern world.

In this episode, Jeremy dives into the making of Decades, including his collaboration with three-time GRAMMY winner Shooter Jennings. He walks us through standout tracks like Barabbas, Dallas, Save You, and Too Much Sugar, sharing the stories and inspirations behind them. Plus, he talks about life on stage, the balance between touring and home life, and what fans can expect from him in 2026.

Jonathan’s Drinking: J Mattingly 6YR Kentucky Bourbon Double Staved