This week, I’m joined by Uncle Kracker for a wide-ranging conversation that dives deep into the stories behind the songs across his entire discography. We explore the evolution of his sound across rock, country, hip-hop, and pop, and how his unique style has continued to resonate with fans for over two decades.

We talk about how his early years touring with Kid Rock as the DJ for Twisted Brown Trucker helped shape his instincts as a solo artist — including lessons learned on the road and behind the scenes. Uncle Kracker also shares his firsthand experience at Woodstock ’99, the story behind teaming up with Dobie Gray for his beloved cover of “Drift Away,” and what it was like co-writing the deeply personal “Letter To My Daughters” with David Allan Coe.

We dig into his collaborations with Kenny Chesney on “When The Sun Goes Down” and “Last Night Again,” the unexpected adult contemporary and country crossover success of “Smile,” and the transition from a major label to an indie release with 2012’s Midnight Special. We also wrap things up by talking about the new chapter of his career — including his latest songs “Reason To Drink,” “Sweet 16,” and “Crusin’ Altitude.”

If you’ve ever wondered how these songs came together — or how an artist navigates decades of change in the industry — this is one you won’t want to miss.

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