Taylor Swift's blue eyes are still putting "those Georgia stars to shame" 20 years later.
The "Tim McGraw" singer's self-titled debut album arrived Oct. 24, 2006, introducing country music to a 16-year-old songwriter with big dreams, curly blond hair and a notebook full of songs about love, heartbreak and finding her place in the world.
Two decades, 12 studio albums and a record-breaking Eras Tour later, Swift's beginnings in Nashville are the subject of a new Tennessean documentary, "Taylor Swift Finding Her Place in This World: Celebrating 20 Years of Her Debut Album."
In 2023, USA TODAY Co. hired me as its first Taylor Swift reporter. Over the next three years, I conducted interviews with people who knew Swift during her first era, hearing firsthand
stories about the rising star before she became one of the biggest names in music.
The documentary, out now, features interviews with Swift's first manager, Rick Barker; early songwriting collaborators Liz Rose and Robert Ellis Orrall; Washington Post journalist and author of "Taylor Swift: The Debut Years," Emily Yahr and Kevin Evers, a Harvard Business Review editor and author of "There's Nothing Like This."
Together, they revisit the decisions, relationships and relentless work that helped launch one of music's biggest careers.
Swift's team did not respond to emailed requests for comment.
'A place in this world'
Before Swift signed with Big Machine Records, she had a development deal with RCA Records. But executives were skeptical that a teenage girl writing songs about her own experiences could succeed in a country music industry dominated by adult male performers.
"She knew how to write a song by herself like no one I'd ever met at that age," Orrall recalls.
After leaving RCA, Swift performed at Nashville's Bluebird Cafe, where she caught the attention of Scott Borchetta, who was preparing to launch Big Machine Records. He promised to support her vision of recording songs she had written.
Rose remembers Swift arriving for songwriting appointments after school, usually Tuesdays around 4:30 p.m., ready to work.
Their collaborations produced some of the debut's defining tracks, including "Tim McGraw," "Teardrops on My Guitar" and "Mary's Song (Oh My My My)."
Shaking a million hands
Getting Swift's early songs heard required more than a record deal. Barker, who helped introduce Swift to country radio before becoming her manager, remembers taking the teenager into radio stations and unconventional venues across the country.
At one smoky bar in Boise, Idaho, he instructed Swift to perform for an hour. By the end, adults who had never heard of her were lining up for photographs and autographs.
The strategy helped challenge assumptions that Swift's music would appeal only to teenage girls.
"Shake a million hands, make a million fans" became an early philosophy behind her growing audience.
Swift also embraced MySpace, communicating directly with listeners at a time when social media was beginning to transform the relationship between artists and fans.
Teardrops on her guitar
The documentary also revisits the making of "Teardrops on My Guitar," including how Swift recruited "One Tree Hill" actor Tyler Hilton to play her crush, Drew.
Hilton remembers meeting Swift backstage at a small show in California before she invited him onstage and surprised him with an offer to appear in her next music video.
The video was filmed at Nashville's Hume-Fogg High School, with fans appearing alongside Swift.
"I didn't even know what was happening," Hilton recalls. "It was just Taylor and I goofing around and hanging all day."
'Taylor Swift' 20 years later
Swift's debut would eventually earn an eight-times platinum certification from the Recording Industry Association of America, representing 8 million album-equivalent units in the United States.
The anniversary also arrives amid continued anticipation for "Taylor Swift (Taylor's Version)." Although fans have speculated about a 20th-anniversary release, Swift has not announced plans or a date for the rerecording.
For the people who knew her before the stadium tours, the documentary offers a look at the teenager behind the songs.
"She's a songwriter first," Rose says. "Always has been."
And Orrall, reflecting on the passing decades, remembers the young artist who arrived in Nashville knowing exactly what she wanted to accomplish.
"It's not for me to say I'm proud of her, but I am," he says. "I'm proud of my role in it early on."
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This article originally appeared on Nashville Tennessean: Taylor Swift's debut album turns 20 | Exclusive new documentary
