Inside Uncle Kracker’s Songbook: The Stories Behind the Songs (feat. Uncle Kracker)

This week I’m joined by Uncle Kracker as we dive into the stories behind the songs that span his entire discography—from his early days to his latest releases. 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 also discuss how his time as the DJ for Kid Rock’s Twisted Brown Trucker helped prepare him for a successful solo career, and what it was like performing at the infamous Woodstock ’99 festival. Uncle Kracker shares memories of collaborating with Dobie Gray on the beloved cover of “Drift Away,” co-writing “Letter to My Daughters” with outlaw country legend David Allan Coe, and teaming up with Kenny Chesney on country hits like “When the Sun Goes Down” and “Last Night Again.”

We dive into the story behind his genre-crossing hit “Smile,” and how it became a chart-topping success in both adult contemporary and country formats. Plus, we talk about the shift from major label to indie for his 2012 album Midnight Special, and highlight the new music he’s been releasing since.

Whether you’re a longtime fan or new to his music, this episode gives everyone a reason to smile!

🎙️ Subscribe now on Apple Podcasts, Spotify, or your favorite podcast platform—and don’t forget to leave a 5-star review to help more music fans find the show! Then, scroll down to hear all of the songs discussed in this episode! 👇