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

We sit down with country singer-songwriter Kelsi Mayne to talk about her latest singles “Someone Who Knows” and “For The Record,” and the winding road that’s shaped her career.

Kelsi opens up about growing up in Windsor, Ontario, balancing music with life as a nationally ranked track athlete and registered nurse, and how playing bar gigs helped spark the realization that music was more than just a side passion. She reflects on releasing her debut album As I Go at the onset of the pandemic, the viral success of its Mad Max–inspired video, and why working closely with her brother has become such a big part of her creative process.

We dive deep into the emotional core of “Someone Who Knows,” written in the aftermath of a cancelled wedding and recorded almost immediately, and how embracing vulnerability has led to her most honest music yet. Kelsi also talks about her high-energy live shows, her infamous “shots and squats” pre-show ritual, performing marathon sets at the Calgary Stampede, and what fans can expect as she looks ahead to 2026.

Jonathan’s Drinking: Penelope Rio

We catch up with country artist Jon Wolfe as he returns to the show to talk about his most personal project to date, Barstool Therapy: Session One, which is out now. Jon opens up about the winding road that took him from a finance degree and the oil industry to the heart of the Texas country scene, and how he found his sound.

Jon dives deep into the concept behind Barstool Therapy, an eight-song collection built around honesty, reflection, and emotional release. We break down the stories behind standout tracks like the title song “Barstool Therapy,” the autobiographical “The Older I Get (More Country I’m Gettin’ to Be),” and his collaboration with Randy Rogers on “Tequila Cowboys.” He also talks songwriting, his trusted co-writing circle, staying proudly independent, and why wearing boots on stage still matters.

Plus, Jon shares how launching his Juan Lobo tequila brand connects to his music, what keeps him relentless after two decades in the industry, what being on stage means to him today, and what fans can expect heading into 2026.

Jonathan’s Drinking: 2XO American Oak

We sit down with indie-folk artist Hunter Metts to talk about his new EP A Crater Wide and the journey that took him from a musical childhood in Nashville to finding his artistic voice after American Idol. Hunter reflects on growing up in a creative family, stepping away from music to pursue software development, and the pull that kept bringing him back to songwriting.

He opens up about the emotional depth behind tracks like “Abielene” and “Blue Ridge Run,” his writing process, the artists who inspire him, and how a viral moment with his breakout single “Weathervane” changed everything. We also get into recording at The Blasting Room, playing multiple instruments on the EP, and the experience of wrapping his first headlining tour and hitting the road with James Bay.

Plus, Hunter shares what being on stage means to him, the stories behind his most personal songs, and what fans can expect heading into 2026.

Jonathan’s Drinking: Three Chord Bourbon Hard Pressed Tennessee Whiskey