Kenny Chesney Surprises Key West Bar Crowd With Impromptu Performance


Kenny Chesney made a surprise appearance at Captain Tony’s Saloon during a recent visit to Key West, Florida.

Captain Tony’s Saloon is supposedly the oldest bar in Florida and has been a notable landmark in Key West since 1851! The bar has hosted numerous singers, songwriters and celebrities including Presidents Kennedy and Truman, Ernest Hemingway, and even Jimmy Buffett who actually got his start at this bar. Captain Tony’s Saloon has been through some wild things since the building was first constructed, but that’s another story for another day.

The “Don’t Blink” singer surprised all in attendance at the local bar when he hopped up to the mic to sing “You and Tequila.”

Wearing a plain white shirt, blue basketball shorts, and a hat flipped backwards, everyone was definitely surprised when the 55 year old took the stage. Chesney proceeded to deliver a beautiful, acoustic performance of the classic song leaving everyone in attendance completely star-struck.

He posted about the performance on social media with a caption that read, “Feeding my creative soul at Capt. Tony’s. Thanks to everyone for allowing me to sit in.”



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“You and Tequila” was certified platinum after its release in 2011 as the fourth single from Chesney’s album, Hemingway’s Whiskey.

The hit song went on to earn two Grammy nominations, two CMA Award nominations, one CMA win, and three ACM Awards.

“You and Tequila” was written by Deana Carter (famous for her hit song, “Strawberry Wine”), and Matricia Berg. The song was penned as a result of a hangover. Seems fitting for a song titled “You and Tequila,” right? The two were supposed to get together to write, but Matricia had been out late the night before and she was suffering from a hangover. This prompted Deana to say something along the lines of “Yeah, it’s just like men … they get in your blood! I can’t drink tequila hardly because it will just get in my blood and it won’t go away. It’s like a guy.”

After more conversation on the subject, the girls started thinking about the meaning behind the phrase, “one is one too many and one more is never enough.” They reached the conclusion that the phrase could include other things in life like men and relationships which ended up sparking the idea for the song.

When Chesney toured with Deana Carter, he heard her sing “You and Tequila” almost every night.

After a painful breakup for Chesney years later, “You and Tequila” became one of his favorite songs. Deana said, “He just sort of nursed his broken heart listening to that song.”

When Kenny decided to record the song, it meant a lot to Deana.

“He said to me, that the song meant a lot to him during that time and it got him through a lot,” she said of Chesney. “So how sweet, first of all. He’s a dear, sweetheart of a friend anyway, so it meant a lot to me that it meant something to him.”

Chesney knew he wanted this song to be a duet; that’s where Grace Potter comes in. Chesney fell in love with the rock singer’s voice, and asked her to sing the song with him. Although it’s not her typical style, she agreed and the rest is history.

Watch the official music video for “You and Tequila” below.