Taylor Swift says she was able to ‘fuel my dreams’ at 18 because Kenny Chesney gave her a check ‘for more money than I’d ever seen in my life’

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In 2023, Taylor Swift is Time’s Person of the Year, but in 2007, she was just another country singer looking for her big break.

During a recent interview with the magazine, Swift opened up about her early days in the industry, including a life-changing gift she received from a fellow musician.

When Swift was 17 years old, she was lined up for a huge opportunity to open for the country star Kenny Chesney — presumably for the Flip-Flop Summer Tour, which was the second-highest-grossing concert series of that year.

“This was going to change my career,” she told Time. “I was so excited.”

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Unfortunately, the tour was sponsored by a beer company, which disqualified Swift due to her age. When her mom broke the news, Swift said she was “devastated.”

When Swift turned 18 in December 2007, she opened a birthday card from Chesney with a check inside. He had written, “I’m sorry that you couldn’t come on the tour, so I wanted to make it up to you.”

“It was for more money than I’d ever seen in my life,” Swift recalled. “I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.”

Kenny Chesney and Taylor Swift onstage in 2015. Rick Diamond/Getty Images for Kenny Chesney
Chesney was also quoted in the story heaping praise upon Swift, particularly her skill as a songwriter.

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“She was a writer who had something to say,” he said. “That isn’t something you can fake by writing clichés. You can only live it, then write it as real as possible.”

The two musicians have remained friends over the years and invited each other to share the stage on numerous occasions.

Chesney made a cameo during Swift’s 2011 Speak Now World Tour, while Swift was a surprise guest on the opening night of Kenny Chesney’s The Big Revival Tour in 2015. Their live duet of “Big Star” was also included on his 2017 tour album, “Live in No Shoes Nation.”

After Swift’s interview with Time was published on Wednesday, Chesney took to X (formerly Twitter) to share his congratulations.

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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. It’s been awesome watching you shine! Congratulations on being @TIME’s Person of the Year. I’m glad TIME sees what I’ve… pic.twitter.com/edlKvqRWQW

— Kenny Chesney (@kennychesney) December 6, 2023
“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.”