Uncle Kracker Has an Amazing Kenny Chesney Confession [Interview]


Uncle Kracker brought new music and new stories to his first-ever interview with Taste of Country.

The “Follow Me” singer revealed why his entire team hated on him for that mega-hit and shared a Kid Rock secret that is still confounding.

He also tuned us into the Jelly Roll collaboration he recorded a decade ago, admitting that he’d followed the “Save Me” singer’s career ever since and found his success to be very satisfying.

Related: The Uncle Kracker + Jelly Roll Song You Never Knew Existed

Uncle Kracker (real name Matt Shafer) is good natured and honest about his life and music. For example, when we asked why it took 12 years for him to record new music, he didn’t try to tell us some story about waiting for his moment or aligning his inner artist with the moon and stars.

  • Uncle Kracker’s Coffee & Beer album dropped in 2024.
  • “Follow Me” and “Drift Away” are his big pop hits, but “Smile” and “When the Sun Goes Down” with Kenny Chesney were hits on country radio.
  • He also co-wrote Kid Rock’s signature hit “All Summer Long.”

“I didn’t even realize there was a gap,” he tells Taste of Country Nights Evan Paul. “I just ended up in a spot where I was no longer on a major label and … all of a sudden, I was just in a spot where nobody was asking for that no more.”

More on Coffee & Beer in a moment — this interview was months in the making, and ToC Nights host Evan Paul had all kinds of questions about the 50-year-old’s life, nickname, family and famous friends. He answered everything!

“It’s always seems like people just think, like, Kid Rock spit me out of his womb and I ended up in Kenny Chesney’s lap,” Kracker jokes.

It is true that his oldest friend introduced him to the country singer, however. Chesney was looking for special guests for a show he had planned in Knoxville, Kracker recalls. “But I didn’t know at the time who Kenny Chesney was,” he adds.

He took the call anyway and was impressed by Chesney’s promise to send his private jet to pick him up. A little while later, they were going to record “When the Sun Goes Down” together.

Sturgeon General Records

Sturgeon General Records

“I started listening to a couple things, and I’d listen to that ‘She Thinks My Tractor’s Sexy’ song. So coming out of ‘When the Sun Goes Down,’ they wanted some ad lib.”

“So it was all just like Uncle Kenny, whatever I could come figure out in the vocal booth, you know?”

The official ad-libbed lyric from the 2004 is “Uncle Kenny’s hotter when the sun goes down.” It’s a treat for anyone who bought the album.

Uncle Kracker Kenny Chesney

Kevin Winter, Getty Images

“You know, we talk all the time — two times a week, easily,” Kracker says. “But just to make sure everybody’s up, you know?”

“We’re all getting older, and it feels like that’s all I’m doing these days is calling and checking in. How are you? Are you feeling good?”

Look for more feel-good on Coffee & Beer. It’s been more than a decade, and Kracker says fans of his old music will appreciate the new.

“Not reinventing any wheels over here, you know,” he says. “Whatever feels good for the day.”

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Gallery Credit: Sterling Whitaker

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Graham Haring

Graham Haring is a versatile writer with a knack for capturing the heart of country music and the stories that surround it. Covering everything from new song releases by icons like Tim McGraw to unexpected cultural phenomena like "The Waffle House Index," his articles bring a mix of humor, depth, and curiosity to the table. Graham’s work often explores the personal side of country music, highlighting the community, family moments, and heartwarming stories behind the headlines. Whether it’s about Keith Urban's benefit shows or a quirky note from the past, Graham's writing resonates with country fans who appreciate a touch of authenticity and a good story.

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