Taylor Swift and Detroit: The story of her early Motor City ties

Long before the globetrotting tours, the tabloid headlines, the Beatlesque frenzy that's driving desperate parents to spend $12,000 for concert tickets, Taylor Swift got a crucial career break in a suburban Detroit parking lot.

In spring 2006, Swift was 16 years old when she made her first trip to metro Detroit. Beyond the fringes of Myspace and certain corners of the country music business, she was virtually unknown.

But the Pennsylvania-born singer-songwriter was precocious, confident and ambitious. And she’d flown to Detroit to wine and dine one of the most influential men in country radio.

It was at the P.F. Chang's on Haggerty Road in Northville Township that WYCD-FM program director Tim Roberts had his first encounter with the young woman who’d go on to become one of popular music's all-time superstars.

"During that dinner, she was the most charming, intelligent young adult I’d ever met in my life," Roberts said. "So far beyond her years, so mature in an intellectual way."

Swift and Roberts were joined that evening by Swift's mom — her constant chaperone in those days — and Jack Purcell of Big Machine Records, the Nashville label that had signed the promising young artist a year earlier. Swift's self-titled debut album was due later in 2006, and its first single, a tender bit of teen romance titled "Tim McGraw," was up first.

After dinner in P.F. Chang's, they headed out to the parking lot. There, on the spur of the moment, Swift fetched an acoustic guitar to perform a personal, impromptu set for the WYCD exec.

"I got in the car later with my wife," Roberts recounted. "And I said, ‘Is it just me, or did those all sound like monster hits?’ "

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Roberts promptly placed "Tim McGraw" into heavy rotation at WYCD, becoming the first major-market radio station in the United States to play Taylor Swift.

Detroit fans headed to Ford Field this weekend for Swift's sold-out concert doubleheader should be aware — and proud — that she has a deep, important history in southeastern Michigan, including some early moments that proved crucial to her career.

Several months after that P.F. Chang's milestone, Swift played the first official tour date of her career, performing at Pine Knob, the summer venue then known as DTE Energy Music Theatre.

Swift was inconspicuous going into that evening of Aug. 25, 2006, but there she was — bottom of a bill featuring Phil Vassar and openers Emerson Drive and Steve Azar. Tickets for the amphitheater show were $10 and $20.

Still, the 16-year-old made sure to stand out for the concertgoers making their way to their seats: Swift kicked off her set with an acoustic rendition of Eminem's "Lose Yourself," shrewdly courting an audience in the rapper's backyard.

Swift was a big Eminem fan, and at the dinner with Roberts that spring, she had discussed her fascination with the movie "8 Mile" and its iconic 8 Mile Road namesake.

"We were blocks away from 8 Mile Road on that side of town," Roberts recounted. "So I took her to Haggerty and 8 Mile, where there's this giant Meijer shopping center."

Leafy, suburban Northville doesn't have quite the gritty Detroit ambience portrayed in Eminem's film.

"She goes, ‘This is 8 Mile?’ " Roberts recalled with a laugh. "I told her, ‘Yeah, but it's a little different if you go east of here. The farther you go that way, the less it looks like this."

"Tim McGraw" was still inching its way up the charts in 2006 when Detroit Lions personnel began plotting out details for the team's traditional Thanksgiving Day game.

"We were looking for an anthem singer, which is always a big deal, because that game is nationally broadcast," said Brandon Bissell, who oversaw the Lions’ game-day entertainment. "We always wanted to make sure we had somebody who's good for that moment."

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Bissell and his colleagues kicked around potential performer names.

"But honestly none of them jumped off the page until Taylor surfaced," he said. "At the time, she only had her one song. That's all the radio play she was getting."

Still, something about the young country singer stood out.

"In sports, we’re always trying to reach a bit younger demographic," said Bissell, who today handles entertainment production for the NFL, MLB and other leagues. "You’ve got this cute young girl, looking like an all-American girl next door, and it just kind of fit, especially with a holiday like Thanksgiving. It worked all the way around."

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And so on Nov. 23, 2006, at Ford Field — where this weekend she’ll hold court for 100,000 fans — 16-year-old Swift, blond ringlets down her shoulders, stood ready to make her national television debut.

"I remember talking to her on the sidelines," Bissell recounted. "I said, ‘Hey, this is cool. You’re taking off, you got this hit going. Has it been a whirlwind? Is it hard for you to manage this new popularity?’ "

Swift didn't skip a beat.

"As straight-faced and confident as a 16-year-old on the planet could be, she said: ‘Oh, no, I knew this was coming. I already have 200 songs written. This was just a matter of time,’" Bissell remembered. "She was so far down that path already."

Risa Balayem, then communications director at Ford Field, watched as Swift delivered "The Star-Spangled Banner."

"She seemed like a tiny child out there. Her guitar was bigger than she was," said Balayem. "Inside Ford Field, watching her standing there on the 50-yard line, it was like: ‘What is this?!’"

Swift and her family were treated to a Thanksgiving spread, complete with turkey, in a Ford Field suite.

"It was a great day," Bissell said. "And who would have known? It's been so interesting to see her career evolve."

Swift would eventually make her Ford Field headlining premiere in 2011, a year after selling out two nights at the Palace of Auburn Hills. On the way, she’d logged plenty of opening dates around town, including several Palace and Pine Knob shows in support of artists such as Brad Paisley, Rascal Flatts, Keith Urban and, fittingly, Tim McGraw.

That early WYCD bond had proved fruitful. Swift became close with the station's drive-time team, "Dr. Don Morning Show with Rachael & Grunwald," frequently appearing in studio, where she was game for impromptu bits on the air.

"She bonded with everybody at my radio station early on. She had a way of doing that — one visit, and and everyone was on Team Taylor," Roberts said. "It was just remarkable how she was able to do that. And I think it's because she was so transparent, honest, innocent, curious and fun all at the same time."

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Swift even wrote a custom version of "Tim McGraw" in honor of the WYCD morning show, but because of the rhyme scheme, she hadn't worked in the word "Rachael." The radio cohost put up a pretend fuss.

"And so during the commercial break, Taylor wrote a sequel on the spot, called ‘I’m Sorry, Rachael,’ " Roberts said. "It shows you her musical genius, that she could come up with something in two minutes. And it was pretty good!"

Roberts and the rest of the music world watched as the young singer-songwriter grew by leaps and bounds, album by album, eventually transitioning from country music to become the world's reigning pop superstar.

As Swift traverses North America on her Eras Tour, Roberts often thinks back to that day in 2006 outside P.F. Chang's.

"She's the most driven person I’ve met in my entire life. She's the most focused," he said. "She just has an insatiable thirst to be creative."

Contact Detroit Free Press music writer Brian McCollum: 313-223-4450 or [email protected].