What Was She Like Before She Was Famous?

This week, Billboard is publishing a series of lists and articles celebrating the music of 20 years ago. Our 2006 Week continues here with a collection of stories from people who knew Taylor Swift during her first year on the music scene.

Wise beyond her years. Smart as a whip. An extraordinary talent.

When you ask industry insiders who crossed paths with Taylor Swift back in 2006 – the year she released her self-titled debut album – many of the same phrases come up again and again. All of them are descriptors you’d generally expect to hear of the person who, in 20 years, would be the biggest artist in the world, and all of them are traits she’s continued to exhibit over time not only as an experienced musician but as a person.

What’s more striking than the ways she’s remained exactly the same since then, however, are the ways that, two decades ago, Swift was just like any other teenage girl.

For instance? “Taylor did not know how to peel shrimp,” country radio coach John Shomby tells Billboard, laughing fondly at the memory of meeting her for the first time in 2006.

It had been the evening before Swift was slated to play for listeners of WGH-FM, which Shomby oversaw at the time as Max Media’s operations manager, and she and her fledgling team at label Big Machine had requested to go out to dinner with him at Bubba’s in Virginia Beach. Shomby remembers a driven young artist who asked endless questions, was forthright about her ambition to have a No. 1 song someday and — aside from some concern that her parents selling their Christmas tree farm back home to support her pursuit of a music career in Nashville might end up in vain — was strikingly confident, self-assured and accomplished. There was seemingly nothing she couldn’t do.

Until the server set her food down at the table.

“She thought the shrimp was gonna be these little round things that you get in Pennsylvania, where she grew up, at TGI Fridays or something like that,” Shomby says, smiling. “Then they walked in with this big plate of shrimp that were the size of her hand.”

He mimes how her famous blue eyes widened at the sight. “She went, ‘Oh, my. How do you eat these things?’”

Shomby’s wife, Marilyn, went about teaching Swift which parts of the shrimp to peel, eat and avoid, and just like that, the cuisine was the latest of many challenges she had conquered. The next day, she would play debut single “Tim McGraw” for Shomby’s team at the station, and afterward, when he told her that the performance had convinced the team to add the song to their on-air rotations, Shomby says: “You’d think we gave her a million dollars.”

This was how Swift spent much of her first year out – traveling the country, meeting different radio executives and, if she was lucky, getting them to play her music. Oftentimes, she succeeded. If the quality of her early songs didn’t win people over, her natural charm usually did. And if not, she didn’t react with any trace of embarrassment or self-doubt – it was simply on to the next.

That’s how Big Machine’s former west coast promoter Rick Barker, who became Swift’s manager for two years after she signed to the label and accompanied her on those radio visits, remembers it.

“She didn’t know any better,” he says, citing one time when they’d planned a big visit to a station and ordered several pizzas for the occasion, just for three people to show up. “You would have thought there were 300. She went up, shook hands, looked them in the eyes and played her heart out in the conference room.”

“She would just always say things like, ‘Do you think they like me? Do you think they’re gonna add my record?’” Barker continues, remembering how their downtime between tour-bus strategy meetings was filled with talk of Swift’s crushes, MySpace posts and Grey’s Anatomy DVD marathons. “I said, ‘Taylor, I’ll [always] be 100% honest with you, as long as you show me you can handle it. If not, I’ll just blow smoke … and tell you how good you are. She goes, ‘No, I want to know. I want to know what I can do better.’”

Swift was also down to try anything. WGN Radio 720’s Lisa Dent, who conducted one of the singer’s very first major radio interviews in 2006 while working at Chicago’s WUSN, says Swift had no hesitations about spending all day on the air speaking unscripted to countless listeners (most of whom likely had no idea who she was), or about taking a microphone out to Michigan Avenue and asking strangers whether they were Cubs or Sox fans for a segment of the broadcast.

“She’s always been fearless,” Dent says incredulously, inadvertently referencing the title of Swift’s massively successful 2008 sophomore record. “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 [with you]. That’s just a part of her DNA.”

Audacy vp of country programming Tim Roberts, who met Swift when she stopped through Detroit on her radio tour, has similar memories. Again, her team had asked to meet for dinner – this time dining at P.F. Changs – and again, she requested to play her music for on-air consideration. Perplexed, Roberts offered to ask the waitstaff if they had a CD player they could borrow.

“She goes, ‘No, I want to play you the songs on my guitar,” he recalls. “Let’s just go out to the parking lot, and I’ll sit in the back of your truck.’”

Outside, she ran through “Tim McGraw” and two other tracks that would become singles from her debut album: “Teardrops on My Guitar” and “Should’ve Said No.” When she was done, Swift – snapping back into teen-girl mode, so to speak – requested to see 8 Mile, the famous namesake and setting of one of her favorite movies she couldn’t stop gushing about over dinner. (Later, when opening for Rascal Flatts in Detroit, she’d play an acoustic-guitar cover of leading man Eminem’s “Lose Yourself.”)

Roberts obligingly took Swift to visit the stretch of road, and “after she left,
I looked at my wife, and I go, ‘Every song she played to me sounded like a No. 1 hit. Maybe it’s just because we spent so much time with her.’ And my wife’s like, ‘No, absolutely. They’re all No. 1s.’”

They were almost right. The first two tracks Swift played would reach No. 2 on the Hot Country Songs chart, after which “Should’ve Said No” became one of Swift’s nine No. 1s on the chart to date.

It’s hard not to notice how certain parts of these memories foreshadow future hallmarks of Swift’s career. In Roberts’ story, she didn’t have a stage on which to perform – so she made her own, evidently spotting his truck at some point before dinner and remembering it later that evening to create an essential opportunity using only what she had at her disposal. That’s not so surprising for someone who would later turn her inability to buy back her own masters into a billion-dollar profit through a series of “Taylor’s Version” releases and her historic Eras Tour.

Then there’s Shomby’s anecdote from the seafood restaurant, which included how “all these guys started looking over” at the tall, blonde and traditionally beautiful young girl he’d walked in with, “but she was completely oblivious.” Instead, she was solely focused on making a good impression with the radio executives – a symbolic counter to how the public would later label her “boy crazy” in dismissal of her talent, meanwhile her career was always the real love of her life (a title fiancé Travis Kelce now shares, of course).

And in Dent’s tale, Swift, after finishing for the day at the Chicago station, taught the radio personality how to take one of those newfangled “selfies.” “That was the first time I’d seen that done,” Dent says, chuckling. “There had to be somebody else in the room, but she took control and said, ‘No, let’s do this.’ It was, I think, an early sign of her controlling her image.”

There are also specific calling cards linking each story. Every person, for instance, volunteers – all unprompted – that 16-year-old Swift followed up each visit with a handwritten thank-you note. (For Dent, Swift went to a nearby stationary store, bought supplies and created a custom piece of colored-pencil art that she then personally delivered to WUSN the next day.) Everyone also remarked on Swift’s “scary good” memory, with Shomby saying, “She knows everybody’s name and everybody’s wife or husband’s name, and their kids.”

“When she played here at Nissan Stadium [in 2019], a bunch of us were backstage,” he continues. “She comes, we’re getting ready to take a picture, and she looks over, and there’s a bowl of shrimp over there. She looks at me and goes, ‘This is kind of ironic, isn’t it?’”

And of course, there’s Andrea. In the periphery of each story from Shomby, Barker, Dent and Roberts, a calm, supportive figure is present in the form of Taylor’s mother, who accompanied her daughter on every step of the radio tour and on most of her journey after that. She served as a constant, protective force (at one point drawing the line that Taylor must wear a coat if she was going to insist on signing autographs for fans lined up in a snowstorm in Utah, Barker remembers). But she also always let the younger Swift take the reins.

“You could tell that she wasn’t, like, a momager,” says Shomby. “Taylor did her thing. Taylor was Taylor.”

At the heart of all these stories is an almost supernaturally determined young girl that was both ravenous for success and deeply interested in forging real connections with the people who could help make that happen. As her star has risen and exploded over time, many have been unable – or unwilling – to reconcile one with the other. She’s been called calculated, manipulative, disingenuous.

But ask the people who knew her from the start, and they’ll tell you something different.

“When she would start winning awards, and people would mock her facial expression or her surprise, it really offended me,” says Dent, whose now-adult son Liam has an autographed poster from Swift – one of his earliest playmates from times spent backstage with her after that initial radio visit – calling him her “favorite boy.” “That was not fake. It wasn’t put on. That was genuine surprise and gratitude.”

Roberts stresses that Swift wasn’t just kind in the moment – she also always remembered who’d helped her and found ways to pay it forward. A few years after meeting at P.F. Changs, she played Palace of Auburn Hills on her Fearless Tour, where a member of her team found Roberts in the crowd mid-show and escorted his party to the end of the stage. Moments later, his face was on the big screens.

“[She] says, ‘This is the song I started my career with, and these people are 100% responsible for me being what I am today,’” Roberts recalls her saying before launching into “Tim McGraw.”

There are also those who attempt to explain away Swift’s success by pointing to her upper-class upbringing or her uber-supportive parents. While certainly helpful, those things are infinitesimal in the long run, argues Barker. After he left his management post with Swift to spend more time with his family – later funneling his experience with her into his book, Music Business for Parents – he started consulting for Sony, where he really got to see, by contrast, just how rare Swift was at 16.

“All these oil dads from Texas were showing up with a blank check and a teenage daughter, thinking that was the magic secret,” he says. “If it were that easy, there would have been a thousand Taylor Swifts.”