WATCH: Kenny Chesney Delivers Impromptu Acoustic Performance In Key West

“Feeding my creative soul at Capt. Tony’s,” the singer wrote on social media.


Madeleine O’Connell

| Posted on

July 31, 2023


4:48 pm

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Kenny Chesney; Photo via Twitter

During a recent visit to Key West, FL, Kenny Chesney popped up for an impromptu performance at Captain Tony’s Saloon. This famed bar has resided in the beach town since the 1850s and has been frequented by many well-known artists, writers, and celebrities over the years.

The country star recently stepped up to the mic in the midst of the casual hub wearing a t-shirt, shorts, and backwards cap as he delivered an acoustic version of his 2011 hit, “You and Tequila.” His spontaneous performance was captured on video and shared to his social media platforms. 

“Feeding my creative soul at Capt. Tony’s. Thanks to everyone for allowing me to sit in,” Chesney wrote in the caption. 

This certified Platinum hit was penned by Matraca Berg and Deana Carter and recorded by Kenny Chesney with featured vocals from Grace Potter, lead singer of Grace Potter and the Nocturnals. It was unveiled in May of 2011 as the fourth single from Chesney’s 2010 album, Hemingway’s Whiskey. “You and Tequila” went on to receive critically acclaimed praise with two GRAMMY nominations, two CMA Award nominations (and one win), and three ACM Awards. 

In the newly-released clip, Chesney can be delivering the soulful storyline of someone trying their best to forget the pain of a past relationship.

“’Cause you and Tequila make me crazy / Run like poison in my blood / One more night could kill me, baby / One is one too many, one more is never enough,” he sings on the chorus. 

YouTube video

This isn’t the first time the “American Kids” singer has taken a break from the sold-out crowds to recharge his passion for music in the intimate setting of a Key West venue. He previously appeared on the stage of the historic Key West Theater as part of his SiriusXM and Pandora Small Stage Series. Here, he performed songs like “Get Along,” “When The Sun Goes Down,” “Save It For A Rainy Day” “Here and Now,” and more.  

He has also made the longstanding bar, Sloppy Joe’s, a frequent stop on his tours in the past. He brought his shows to the popular stage in 2008, 2009 and 2016.

Kenny Chesney’s most recent headlining I Go Back Tour wrapped up earlier this year after its run across the U.S. with stops in State College, PA., Greensboro, NC, Grand Rapids, MI, Grand Forks, ND, Sioux Falls, SD, Jacksonville, FL, Fort Wayne, IN, Lexington, KY, and more. With this stint of shows, Chesney got to visit arenas that he hasn’t played in several years, which made this trek even more special to the eight-time Entertainer of the Year. 

Kenny Chesney; Photo by Jill Trunnell
Kenny Chesney; Photo by Jill Trunnell

Once he was off the road, the singer/songwriter caught up on some much-needed rest and relaxation on island time. He took to social media to share a glimpse into his time off, which included a post-tour celebration with his longtime friend and tourmate, Kelsea Ballerini. 

He also made sure to share his gratitude for all the fans that came out to see his shows and who have continued to support him through each endeavor. 

“Now that I’ve gotten off island and had a moment to reflect, I want to thank everyone who came to the two shows at @TheWharfAmp in Orange Beach, AL. What a magical couple nights and what a magical tour. The #IGOBACKTOUR with @KelseaBallerini will be ringing in my head for the rest of my life. Thanks to everyone that was a part of it. I love you all,” he wrote at the time. 

Over the summer, Kenny Chesney has continued to perform at a variety of carefree festivals, however, he has yet to announce his next set of tour dates. 

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Madeleine O’Connell graduated from North Central College with a bachelors degree in Journalism and Broadcast Communications before deciding to pursue her studies further at DePaul University. There, she earned her masters degree in Digital Communication & Media Arts. O’Connell served as a freelance writer for over two years while also interning with the Academy of Country Music, SiriusXM and Circle Media and assisting with Amazon Music’s Country Heat Weekly podcast. In addition to Country Now, she has been published in American Songwriter, Music Mayhem, and Holler.Country. Madeleine O’Connell is a member of the Country Music Association and the Academy of Country Music.