Watch a brief clip of Taylor Swift performing the opening number on the first night of her "Reputation" stadium tour in Glendale, Arizona, Tuesday, May 8, 2018. Arizona Republic


Rick Flatt was hosting an employee picnic at Sleepy Hollow Sports Park when his phone rang.

A Des Moines country music station, 97.3 KHKI, wanted to know if the park was booked that afternoon. They had a young singer and her mother in the studio and they wanted to throw a pop-up show for a few local fans.

Sure, said Flatt, the park's owner. Why not?

About 15 people — park and radio staff plus a handful of fans — mingled an hour later under a shelter house to hear the teen.

Some exchanged small talk. Others cleaned as the crowd dwindled.

Then she started singing. That’s when everyone paused … and listened.

“I remember specifically the first song,” Flatt said. “She introduced it by saying, ‘I just recently wrote this song. It’s kind of odd because the song is titled after someone, but it’s really not a song about the person.’ ”

The song? “Tim McGraw.”

But … how?

Taylor Swift playing at Sleepy Hollow started the way many things in country music start — with a local radio station.

She spent most of 2006 — the year she played the park, organizers recall — shaking hands and signing autographs for country stations coast-to-coast. That included a stop at KHKI “NASH” FM, then known as The Hawk.

Big Machine Label Group, her label, released “Tim McGraw” to radio that June, with a self-titled debut album dropping in October.

Related: 'My loyalties are here': Longtime Des Moines radio host looks toward life after KIOA

“Radio tours for most artists last six weeks,” she told CMT in December that year. “Mine lasted six months. That’s because I wanted it to. I wanted to meet every single one of the people that was helping me out.”

And a decade ago, it wasn’t uncommon for an up-and-coming artist to campaign face-to-face for airplay, said 92.5 KJJY morning show host Eddie Hatfield.

Hatfield’s seen the story play out time and again in his three decades of broadcasting.

One time, it’s Rascal Flatts playing the Perkins on Hickman Road (with $0.92 all-you-can-eat pancakes, of course) and on another occasion, it’s Alan Jackson signing records in the Merle Hay Mall.

“You find (artists) who are all excited and then it slides into a job,” Hatfield said. “No matter how great being a star is, it’s still a job.”

“But some people don’t lose that excitement — and Taylor’s one of them.”  

More: Rascal Flatts coming to Des Moines, this time as a restaurant

At the shelter house

A tall teenager with curly blonde hair and an acoustic guitar, Swift played about a half-dozen songs that afternoon, including the never-released number “Permanent Marker.”

Her songwriting entranced the intimate audience, Flatt said.

It’s what he remembers most from the afternoon.

“She was so heartfelt in the songs,” he said.

A songwriter before a star, Swift captured a generation’s coming-of-age story by singing through love, heartbreak and the melodrama in-between. And Des Moines native Darby Elliott, daughter of former KHKI morning host Andy Elliot, was one of the first to take her side.

She saw firsthand at Sleepy Hollow Swift’s personalized touch on and off stage — something she would be known for in the years following that radio tour.

Elliott spent that day with Swift, dancing in restaurant parking lots (a trip to La Pizza House followed the show) and keeping company as the singer personalized each autograph.

“I was sitting next to her, she was signing autographs, and I said, ‘You’re not gonna be able to do that forever,” Elliott, 23, recalled.  “And she said, ‘Oh, OK. Yeah, right.’ And now she’s Taylor Swift and probably doesn’t even have time to scribble her initials."

Related: Iowa’s ‘Idol’ winner Maddie Poppe is playing a home state concert in August (and it’s free!)

Still, she showed appreciation that day for the chance to share her songs with a few new faces, Flatt said.

“She opened and finished by saying ‘I’m Taylor Swift. I hope to someday be doing something big with my career,’ ” Flatt said. “That was kind of it.”

That was it … until she returned in 2009, playing to a sold-out Wells Fargo Arena crowd of 13,620. She returned again in 2010, 2011, 2013 and 2015. Each show? Sold out.

Now a 28-year-old woman playing back-to-back Soldier Field shows in Chicago this weekend, it’s old stories from a shelter house and new songs of a “big reputation” that keeps a generation of fans wanting more from their pop star.

“I miss her in country music, for sure, but I know every word to every song of all her albums,” Elliott said. “... I still love it. I love all of it.”

"So, About That Time…," a new series from the Register’s Matthew Leimkuehler, highlights Iowa’s obscure and overlooked musical moments. Have a story you’d like to share? Reach him at or by phone at 515-284-8358.

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