Ashley Cooke’s ’10-Year’ Dream Comes True Thanks To Her ‘Absolute Idol’ Kenny Chesney

Ashley Cooke fulfilled a decade-long dream when she joined Kenny Chesney on stage for a special performance during the Tortuga…


Lauren Jo Black

| Posted on

April 17, 2023


1:40 pm

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Kenny Chesney, Ashley Cooke; Photo via Instagram

Ashley Cooke fulfilled a decade-long dream when she joined Kenny Chesney on stage for a special performance during the Tortuga Music Festival over the weekend.

Chesney, who closed out the three-day beachside festival, took to the stage at 10PM to deliver his headlining set after a brief rain delay. It was then that he invited Cooke to join him to perform his chart-topping hit, “When The Sun Goes Down.”

“I watched side stage as he had [the crowd] in the palm of his hands… until the lightning came, and the stage managers had to pull him off,” Cooke explained. ”We all went back to his tent by the bus and took cover while it rained. We waited about 45 mins, and everyone said Kenny would be able to go back on around 10pm. Out of nowhere, someone from his team pulls me out of the tent crowd and very calmly asks, ‘Hey, do you wanna sing ‘When The Sun Goes Down’ with Kenny?’”

“Next thing you know, I’m side stage when ‘When The Sun Goes Down’ starts and Kenny yells ‘Ashley! Come here, baby!!’” she continued. 

Wearing a pair of loose-fitting jeans and a tank top, Cooke joined Chesney on stage for a moment she’ll never forget. 

“I ran out, barefoot and buzzing on both backstage espresso martinis and teenage dreams and got to take the Main Stage with the absolute idol that is Kenny Chesney,” she recalled. 

The unforgettable experience served as a full-circle moment for Cooke, a Florida native who previously attended Tortuga Music Festival as a fan.

“Sunday night was pulled straight from a 10-year-long manifestation dream. I watched Kenny Chesney from the sand on the Main Stage at Tortuga in 2013 and dreamed of one day getting to play on that stage. Here we are in 2023 and not only did I get to play an entire set on that stage… Kenny also very last minute pulled me up during his set.”


10 years ago watching @kennychesney from the crowd —> tonight, singing with him on stage. thankful for new friends and memories. 🤍

♬ original sound – Ashley Cooke

Following their performance together, Cooke shared her gratitude for the eight-time Entertainer Of The Year. 

“Artists like him are the reason the country music genre is truly a family. He isn’t afraid to take a bet on the next generation. He wants to love greatly and pass down all he’s learned along the way. They say to never meet your heroes – but I say if your hero is anything like Kenny Chesney… Soak up every damn moment you can.”

Cooke also posed for a photo with Chesney backstage before taking a cold plunge in Chesney’s tour ice bath. “Did an ice bath with Kenny Chesney. Guess how long I lasted,” Cooke wrote. 

Kenny Chesney, Ashley Cooke; Photo via Instagram
Kenny Chesney, Ashley Cooke; Photo via Instagram

Chesney also took to social media to graciously thank Cooke for joining him on stage.

“Thank you, Ft. Lauderdale and @festivaltortuga for another fun night by the ocean. Our fourth time playing this festival and even the weather couldn’t stop the party. Special thanks to @theashleycooke for coming up on When The Sun Goes Down. What a blast.”

The fast-rising country star is a longtime fan of the “American Kids” singer, who she previously revealed is her dream duet partner.

“Kenny Chesney because I’ve always fangirled over his music and I’m from Florida so I love his island vibe,” she told previously Music Mayhem in an interview.

Cooke often shares clips covering Chesney tunes on her TikTok. She recently covered “Everyone She Knows” and “Knowing You,” a song she said “wrecks me to my core.”

Additionally, Ashley Cooke is serving as support on Brett Young’s headlining 5, TOUR, 3, 2, 1 tour, produced by Live Nation. The 17-city tour kicked off on March 30 in Columbus, Ohio and wraps up on May 20 in Los Angeles, California at the Greek Theatre.

Following the Brett Young tour, Cooke will join Luke Bryan on select dates of his Country On Tour. In between shows with Young and Bryan, Cooke is also headlining several of her own concerts.

Cooke is also scheduled to perform at several festivals throughout the summer, including CMA Fest, Tailgate N’ Tallboys Bloomington, Bonnaroo, Country Jam Colorado, Wild West Fest, Cavendish Beach Music Festival, Country Concert and more. 

Meanwhile, Kenny Chesney is in the midst of his I Go Back Tour, which kicked off on March 23 in Charlottesville, Virginia and continues through May 27. The trek features support from Kelsea Ballerini. 

Presented by Blue Chair Bay Rum, the I Go Back Tour finds Chesney returning to his roots as he visits arenas and cities that he played on his rise to superstardom.

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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.