Remember When Kenny Chesney Had a No. 1 Hit With Uncle Kracker?

Kenny Chesney is well-known for his laid-back beach songs, and he crossed genre lines when he teamed with Uncle Kracker for “When the Sun Goes Down.”

Uncle Kracker’s real name is Matthew Shafer, and he got his start in music as a deejay for Kid Rock, serving as a turntablist in his fellow Michigan native’s backing group, Twisted Brown Trucker.

He joined Chesney on “When the Sun Goes Down” in 2004, and scored his first-ever country hit when the title song and second single from Chesney’s album of the same name reached No. 1 on Billboard‘s Hot Country Singles & Tracks chart on April 3 of that year.

Though Uncle Kracker saw success in country music with his first outing, he admits the genre was a stretch for him initially.

“I had always thought about country, but it’s a very tricky thing,” he tells the Boot. “I remember entertaining the idea of dabbling around with the country stuff after the Chesney thing, and I thought, you know what, I’ve seen so many guys come through and try to do country records and just jump on the country bandwagon without giving it the respect it deserves.

“And I said to myself, if I ever did something like that, you always have to pay respect to the people you need to pay respect to, not just in country music but in life. And I’ve always been a firm believer that with just the right idea, maybe further down the road I’ll get there the right way.”

After scoring a No. 1 hit with Chesney on “When the Sun Goes Down,” Uncle Kracker would go on to release “Smile,” from his Happy Hour album, in 2009. The song became a multi-platinum hit and reached the Top 10 on both the country and pop charts.

Uncle Kracker followed that single with a duet with Kid Rock, “Good to Be Me,” which reached the Top 30 in both genres.

In 2024, Uncle Kracker joined Zac Brown Band and Megan Moroney on the road with Chesney to open his 2024 Sun Goes Down Tour.