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Kenny Chesney<\/a> is well-known for his laid-back beach songs, and he crossed genre lines when he teamed with Uncle Kracker<\/a> for “When the Sun Goes Down.”<\/p>\n Uncle Kracker’s real name is Matthew Shafer, and he got his start in music as a deejay for Kid Rock<\/a>, serving as a turntablist in his fellow Michigan native’s backing group, Twisted Brown Trucker.<\/p>\n 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<\/em>‘s Hot Country Singles & Tracks chart on April 3 of that year.<\/p>\n Though Uncle Kracker saw success in country music with his first outing, he admits the genre was a stretch for him initially.<\/p>\n “I had always thought about country, but it\u2019s a very tricky thing,” he tells the Boot<\/a>. “I remember entertaining the idea of dabbling around with the country stuff after the Chesney thing, and I thought, you know what, I\u2019ve 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.<\/p>\n “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\u2019ve always been a firm believer that with just the right idea, maybe further down the road I\u2019ll get there the right way.”<\/p>\n 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<\/em> album, in 2009.<\/p>\n READ MORE:<\/em> Kenny Chesney Is STILL Mad That This Song Got Away From Him<\/a><\/strong><\/p>\n \u00a0<\/p>\n The song became a multi-platinum hit and reached the Top 10 on both the country and pop charts.<\/p>\n Uncle Kracker followed that single with a duet with Kid Rock, “Good to Be Me,” which reached the Top 30 in both genres.<\/p>\n In 2024, Uncle Kracker joined Zac Brown Band<\/a> and Megan Moroney<\/a> on the road with Chesney to open his\u00a02024 Sun Goes Down Tour<\/a>.<\/p>\n What truly separates Chesney \u2014 a 2025 Country Music Hall of Fame inductee \u2014 from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney’s best were released after<\/em> 2010. It’s there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.<\/p>\n We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff\/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.<\/p>\n<\/div>\n Gallery Credit: Billy Dukes<\/p>\n<\/div>\n Kenny Chesney has sold his 4-bedroom, 9-bathroom, 12,599-square-foot hilltop estate in Tennessee for $11.5 million, and pictures show an opulent Mediterranean villa that is lavish even by the standards of other celebrity mansions.<\/p>\n<\/div>\n Gallery Credit: Sterling Whitaker<\/a><\/p>\n<\/div>\n<\/div>\nWho Is Uncle Kracker?<\/h3>\n
What Was Uncle Kracker’s First Country Hit?<\/h3>\n
What Are Some of Uncle Kracker’s Hits?<\/h3>\n
25 Best Kenny Chesney Songs That Prove He’s Country Music Hall of Fame Worthy<\/h2>\n
PICTURES: See Inside Kenny Chesney’s Spectacular $11.5 Million Tennessee Estate<\/h2>\n