"She goes, 'No, I want to play you the songs on my guitar. Let's just go out to the parking lot, and I'll sit in the back of your truck’”: Back in 2006, a “fearless” Taylor Swift took a hands-on approach to getting her music played on the radio

Whether you believe that Taylor Swift deserves her current level of superstardom or not, few would deny that she’s worked hard for it, and the lengths that she went to to get her early music on the radio have now been revealed.

To mark almost 20 years since the release of Tim McGraw, Swift’s debut single, Billboard spoke to various people who came into her orbit right at the start of her career, and all tell a tale of someone who was fiercely determined to do what it took to get to the top.

In particular, they highlight Swift’s willingness to build relationships with radio stations so that they’d play her music – and that usually involved performing it to staff in person.

When visiting Detroit, for example, she dropped in at Audacy and met up with VP of country programming Tim Roberts, who recalls that Swift asked if she and her team could meet them for dinner. Once there, she said that she wanted to play Roberts some of her songs – including Tim McGraw – so he asked the restaurant staff if they had a CD player he could borrow.

Swift, though, had other ideas: "She goes, 'No, I want to play you the songs on my guitar," says Roberts. "’Let's just go out to the parking lot, and I'll sit in the back of your truck.’”

WGN Radio 720's Lisa Dent, meanwhile, says that, when she hosted Swift in 2006 at Chicago’s WUSN, she was happy to engage with listeners both on air and in person.

"She’s always been fearless,” she says. “She engages people, and she does that by listening intently - even at that age, you would feel like you were the only person in the room when she made eye contact. That's just a part of her DNA."

Which isn’t to say that everyone knew right away that Taylor Swift was going to become the biggest pop star on the planet. However, speaking to Music Week in 2020, Tim McGraw co-writer Liz Rose recalled that there was always something about her.

“I first met Taylor Swift when I played a writers’ room at a record label and she was there,” she revealed. “She heard a couple of my songs and asked if I would write with her. That’s what I’ve learned in this business: you’re never too big to write with a new artist. We had a great time the first day we wrote and we just kept writing and writing. There’s nothing like songwriting with her.

“Did I think she’d become the biggest star in the world? You don’t think that, but I did know that she was special. With her drive and her talent, I knew that she was going to do something, absolutely.”