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The Bobby Bones Show

The Bobby Bones Show

BOBBYCAST #690 - Brothers Osborne on the Scary Future of Country Music, Chris Stapleton's Dad Advice & Why They Wouldn't Make It Today

Oct 22, 2026 · 1h 0m

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About this episode

Brothers Osborne return to the BobbyCast to catch up with Bobby about everything that's changed since their last visit. John opens up about becoming a father to twins and shares some of the best parenting advice he received from Chris Stapleton. The guys also talk about their new album Watertown and why they believe they wouldn't make it if they were starting their careers in today's music industry.They get into the pressure artists face to become social media personalities, why it's harder than ever to make a living in music, and their concerns about the rise of AI-generated songs. Plus, they share stories about John Mayer, Hank Williams Jr., and how some of their biggest songs came…