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