A timeline of Taylor Swift and Kenny Chesney's friendship (2024)

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Chesney met Swift when she was an unsigned teenager.

According to a 2017 interview with Taste of Country, Chesney and Swift met at an airport before she'd even inked her first record deal at the age of 15.

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Chesney wanted Swift to open for his 2007 tour, but she was too young.

When Swift was just 17 years old, she was slated to join Chesney on the road — either for the 2007 Flip-Flop Summer Tour or the 2008 Poets & Pirates Tour, based on the timeline.

However, the country superstar had recently signed a sponsorship contract with Corona.

"There was some sort of legal, contractual thing where people weren't comfortable with having an alcohol-sponsored show and having a 17 or 18-year-old on the show," Chesney recalled during a radio interview in 2011. "So, I had to call Taylor and tell her that she couldn't do that tour. And I gave her, as a 'I'm sorry' present, I gave her a lot of money."

At the time, Swift was still in the early stages of her career; she hoped the tour would be her big break. She told Time she was "devastated" when she couldn't open for Chesney's tour.

However, she also said his generous gift changed her life.

"It was for more money than I'd ever seen in my life," Swift told Time. "I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams."

Not long after, Swift and Chesney were both nominated for entertainer of the year at the 2009 CMA Awards. Swift took home the top prize, becoming the youngest artist ever to do so.

"So, I'm backstage and I come up behind her and gave her a hug and said, 'I want my money back,'" Chesney recalled. "I haven't gotten it back yet, but maybe I will one day, who knows."

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They continued to interact at country music events and spoke highly of each other in interviews.

"He is one of the coolest, most affectionate, gracious people that I've met in the music industry, and he's always reaching out to me to say 'hey' and check up on me and see how I'm doing," Swift said of Chesney in 2011, per Taste of Country. "It seems like he has this weird intuition to know when I need someone to stop in and say, 'How are you.'"

During an interview on the Country Countdown USA radio show in 2011, Chesney also revealed that he and Swift were e-mail buddies.

"Taylor and I are very good friends and I've known her for a while, and I know the ups and downs that an artist goes through," he said.

Chesney made a cameo during Swift's 2011 Speak Now World Tour.

During a tour stop in Nashville during the "Speak Now" era, Swift invited Chesney to share the stage for a duet of his 2003 single "Big Star."

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Swift returned the favor during Chesney's 2015 Big Revival Tour.

Swift flew to Nashville to surprise Chesney for the opening night of The Big Revival Tour, which also happened to be Chesney's 47th birthday.

Once again, they performed a duet of "Big Star," with Swift arriving halfway through the song to surprise the crowd.

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Their live duet of "Big Star" was featured on Chesney's 2017 live album.

Swift is featured on track three of Chesney's 2017 tour album, "Live in No Shoes Nation."

Their live rendition of "Big Star" was recorded during her surprise cameo on his 2015 tour. When her vocals kick in, you can hear the audience start to scream.

"She surprised me on my birthday and we were able to capture that moment for this record," Chesney told Taste of Country in 2017. "I wanted to surprise the audience. She was surprising me and I wanted to surprise the audience and honestly, Taylor Swift needs no introduction."

Chesney also said "Big Star" is a special song for the duo because it echoes Swift's own life.

"It's still an incredible moment because, in a way, that song represents her story," he wrote on Facebook. "I'm grateful for her friendship and for topping off an incredible birthday."

The "Big Star" lyrics tell a story about a small-town girl with a big musical talent, determined to become a star.

"She doesn't care anymore that her high school girlfriends cut her down," he sings in the bridge. "The only thought she entertains is where they are / And where she is now."

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Chesney praised Swift when she was named Time's Person of the Year in 2023.

Chesney was one of several artists quoted heaping praise upon Swift in her cover story for Time.

"She was a writer who had something to say," he told the magazine. "That isn't something you can fake by writing clichés. You can only live it, then write it as real as possible."

Swift expressed her gratitude for Chesney on social media.

"I was blown away to see quotes from people I adore and admire like Stevie Nicks, Greta Gerwig, Shonda Rhimes, Phoebe Bridgers, Natalie Maines, Kenny Chesney, and Lucian Grainge," she wrote on X (formerly Twitter) when she shared the article link.

Chesney also reiterated his admiration with his own post on X.

"Taylor, I knew looking in your eyes that first time on stage with us, you had 'it.' The hunger, that something special… A gift not everyone has to connect," he wrote. "It's been awesome watching you shine!"

"I'm glad TIME sees what I've always loved about your music, your art & you as a human being," he added. "I'm so proud of you & I love you."