Kenny Chesney Recalls the Moment He Fell In Love with the Island Life

Kenny Chesney has embraced his love for the island lifestyle through his music for 20 years and on Monday morning…


Lauren Jo Black

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February 1, 2021

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Kenny Chesney; Photo by Allister Ann

Kenny Chesney has embraced his love for the island lifestyle through his music for 20 years and on Monday morning (Feb. 1), he opened up about how he initially fell in love with the Virgin Islands during an interview with Bobby Bones on The Bobby Bones Show

As his latest single, “Happy Does,” climbs toward the No.1 spot at country radio, Chesney reflected on the moment he became what Bones refers to as the “island Kenny.” 

“The first time I ever went down the islands, I shot a music video for ‘How Forever Feels,’ the superstar shared. “We had a day off and I took the ferry over to the other island and Bobby, it was crazy. I was walking up the street and there was this bar and they had the door open and I heard George Strait coming out of that bar and I walked in and I stuck my head in, and I said, ‘is that really George Strait?’”

Much to Chesney’s surprise, two men inside the bar recognized him. 

“They went, ‘Yeah, and are you Kenny Chesney?’”

Those two men are from Kansas City and remain Chesney’s friends to this day. The East Tennessee native admitted he was a bit taken back by the fact that they recognized him because it was still so early in his career. 

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Chesney went on to share how a photo he posted on New Year’s Day of him on a boat in 2001 marked the beginning of his “island journey” and told Bones how the folks he knows from St. John don’t know him as an entertainer, just as a neighbor. 

“When they come out to the shows, you know, they only know me as someone they’ve seen on the island for a lot of years now, but when they come out to a show, they’re really confused because they don’t know the other person,” he explained. “They can’t believe it, you know, because they just see me as a local and in their grocery store.” 

Chesney also spoke with Bones about having more than 30 No.1 hits. Click above to listen to the full interview. 


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Chesney’s latest single, “Happy Does” is featured on his chart-topping album, Here and Now.

Written by Brock Berryhill, Brad Clawson, Greylan James and Jamie Paulin, “Happy Does” reminds listeners to embrace what life throws at them and make the most of what they have, even if it may not be much at all.

“Happy is as happy does/ Grab a six-string, find a rope swing/ Hang a palm tree in your truck/ Drink a beer just because/ Steal a slow dance in a rainstorm/ And a kiss from who you love/ Laugh and live with a half-full cup/ Yeah, happy is as happy does,” he sings on the chorus.

The eight-time Entertainer of the Year may not have had a hand in writing the carefree anthem, but he envisioned himself when he first heard the song.

“That line about ‘every pickle jar dollar,’ that was me in college, playing for tips in this little bar in West Virginia,” Chesney previously shared. “I’d rent a pretty basic sound system, go over the line, set up, play three sets, tear down and drive home, so I could turn the stuff back in at the music store, go through the drive-in, get a breakfast sandwich and get on to class.”

“To do what you love, to chase a dream is a really special thing,” he added. “When you’re doing that, you find a whole lot of happiness with just a little bit of something. The chorus with the rope swing, the palm tree off the rearview mirror, a kiss from someone you love… With all this unknown and all this who knows, it felt like the song people were going to need this summer. The melody feels good, and the track makes you smile! So ‘Happy Does’ is a pretty good post-it note when you’re having a bad day, or even just a day.”

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Lauren Jo Black

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Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.