When Taylor Swift turned 18, she was handed a life-altering birthday card.

At 17 years old, Taylor Swift landed what she thought would be the opportunity of a lifetime.

It was 2007, a few years before Kanye West would wrestle the microphone from Swift's hands at the VMAs. A year before she would be nominated as the Best New Artist at The Grammy Awards and still months away from playing sold-out concerts where she headlined across the United States.

Back then, she was still just a teenager balancing school with her aspiring music career when she landed the opening slot of country star Kenny Chesney's summer tour. At that point, it was the most significant opportunity of her life.

Watch: Taylor Swift announces her new album at the 2024 Grammy Awards. Post continues after video. 

Video via Grammy Awards.

"This was going to change my career," she told TIME in 2023, having been aptly named the magazine's Person of the Year. "I was so excited."

But then one day she came home to find her mother, Andrea Swift, sobbing on the front steps of their house. Taylor was worried — she thought there had been a family tragedy.

Instead, it had to do with her gig on Chesney's tour. The beer company Corona had sponsored it. Being under the age of 21 meant Swift could no longer be part of the opener.


"I was devastated," Swift recalled. So was Andrea who had supported and nurtured her daughter's musical talents since birth.

"There would always be an escape hatch into normal life if she decided this wasn't something she had to pursue," Andrea told Entertainment Weekly back in 2008 when her career was only really beginning to take off. "And of course, that's like saying to her, 'If you want to stop breathing, that's cool.'"

After all, Swift's mother had been on the road with her since 2006 when she'd made her singing debut onstage at the Grand Ole Opry. They had even moved their family in 2003 when she landed a record deal with Sony/ATV Publishing.

It had been her daughter's dream to go further into the music industry and she, along with her husband Scott Swift, desperately wanted her to succeed. So the opportunity being pulled from beneath her daughter had a profound impact on the entire family.

But the devastation wouldn't last long because she turned 18 years old later that year, in December 2007, and celebrated with a birthday party. While Chesney hadn't been in attendance, his promoter was and handed Swift a card.

It was from Chesney and it read, "I'm sorry that you couldn’t come on the tour, so I wanted to make it up to you."


Inside the card was a cheque with Swift's name on it.

"It was for more money than I’d ever seen in my life," she explained. "I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams."

Taylor Swift and Kenny Chesney, 2015. Image: Getty.

Chesney's support of Swift went far as by 2009, they were both nominated for Entertainer of the Year at the 2009 Country Music 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, per Business Insider. "I haven't gotten it back yet, but maybe I will one day, who knows."

A few years later, Swift said he is "one of the coolest, most affectionate, gracious people that I've met in the music industry."

"He's always reaching out to me to say 'hey' and check up on me and see how I'm doing," she said, 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.'"

Chesney and Swift have been friends for more than a decade now and have performed together since the 2007 disaster that left her "devastated".

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'.

Kenny Chesney and Taylor Swift, 2011. Image: Getty.


And then in 2015, Swift flew to Nashville to surprise Chesney for the opening night of his The Big Revival Tour, which also happened to be his 47th birthday.

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

Their live rendition was recorded during his 2015 tour and later made into a single on his 2017 tour album Live in No Shoes Nation.

"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 confessed that '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 lyrics tell a story about a small-town girl with a musical gift, 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."

Their special friendship, which existed long before Chesney's generous donation was mentioned in a post to Swift from the singer, where he said she had "something special".

"Taylor, I knew looking in your eyes that first time on stage with us, you had 'it,' Chesney wrote following her TIME interview. "The hunger, that something special... A gift not everyone has to connect. It's been awesome watching you shine! Congratulations Person of the Year.

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

Feature Image: Getty.

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