Taylor Swift

circa 2003

Country's Determined Darling

At 13, Taylor Swift, who began writing songs at age 5, signs with RCA Records. A year later, she gets out of the contract because she doesn't want to sing other writer's songs. Around that time, she becomes the youngest songwriter to sign a publishing deal with Sony – but doesn't want her songs sung by other artists. "She has a real inner vision, a real inner directedness," says Scott Borchetta, who eventually urges Swift to write and sing under a recording contract with his indie label, Big Machine Records.

2006

Swift's "Tim McGraw"

Swift's breakout single, "Tim McGraw," which she began writing in her freshman math class, hits country radio airwaves. The song is about hoping her love thinks of her when he hears Tim McGraw's music. It peaks at No. 6 on the Billboard Hot Country Songs chart. While performing her hit at the Academy of Country Music Awards in 2007, Swift finally meets McGraw when she walks into the audience to serenade McGraw and his wife, Faith Hill (right).

October 24

Taylor's Self-Titled Debut

Big Machine Records releases the 16-year-old's self-titled debut album. "I didn't come in to this to be baby-sat," Swift tells the AP about having creative control. She also says she isn't afraid of the tough country music industry: "Not by any measure. I'm intimidated by the fear of being average." Her debut eventually sells more than 2.5 million copies.

2007

November 07

On CMA's Horizon

At the Country Music Association Awards, 17-year-old Swift performs her latest hit, "Our Song," before winning the coveted Horizon Award. "I can’t even believe that this is real," she says during her acceptance speech. "I want to thank God and my family for moving to Nashville so I could do this. The fans – you have changed my life. This is definitely the highlight of my senior year!" Past winners include Garth Brooks, The Dixie Chicks and Carrie Underwood.

December 06

Grammy Acclaim for Miss Swift

Called upon to help announce the Grammy nominations, Swift is ecstatic when she hears her own name in the category of Best New Artist. An ecstatic Swift rushes over to fellow announcers, Foo Fighters' Dave Grohl (left) and Taylor Hawkins, and hugs them. "Don't worry, Taylor," Grohl says, "you got it in the bag." At the ceremony, another talented singer-songwriter, the troubled Amy Winehouse, nabs the trophy.

December 13

Taylor Turns 18!

To ring in her milestone 18th birthday, Swift's parents, Andrea and Scott, throw her a pink party in Nashville. The birthday girl parties with some 200 guests, including Kellie Pickler. "This party is our birthday gift to her," her mother tells PEOPLE. "She knows the real gifts in life are relationships." But the best part about turning 18? "I wanted a No. 1 record, and I got that," Swift says of her chart-topper "Our Song." "And I got something I didn't even ask for: a Grammy nomination. It's been a great year."

2008

April

Taylor Covers Blender

Swift appears on the cover of Blender, where she discusses her love life – or lack thereof. "I just don't have the time," Swift says of dating, revealing that she hasn't kissed a boy in almost two years. When asked about her dream prom date, she says, "Perez Hilton! Your prom date is supposed to be fun and hilarious, and I think I'd have more fun with Perez than with anyone else." The country music darling also lands on PEOPLE's Most Beautiful list.

April 14

Taylor Tops CMT Awards

At the fan-driven Country Music Television Awards, Swift – barefoot for most of the show – nabs two major prizes, including Video of the Year. "Are you sure? Are you serious?" Swift says in disbelief as she accepts her first award for Female Video of the Year. Of her lack of footwear, she later tells PEOPLE, "I walked by Faith Hill and I was like, 'This hurts so bad.' And she was like, 'Take them off,' Faith Hill told me to. So I did it."

May 18

This One's For Mama!

"Mom, thank you so much. I love you. This is for you!" Swift tells the crowd as she tearfully accepts the award for Top New Female Vocalist at the 2008 Academy of Country Music Awards. She also gives a dripping wet performance of "Should've Said No," during which water pours on her from the ceiling.

August

Taylor Dates A Jonas Brother

Although Swift says Joe Jonas, 19, is just a friend, the Jonas Brothers cutie fuels rumors when he turns up at her concert. Through her rep, Swift says of Jonas, "He's an amazing guy and anybody would be lucky to be dating him." While Jonas recently said, "She’s a great girl...I think anybody would love to go on a date with her." In October, they call it quits, and Swift writes a track, "Forever and Always," inspired by their breakup.

2008: November 11
Fearless
Swift's sophomore effort, Fearless, tops the Billboard charts with 592,000 copies sold in its first week. Rolling Stone calls Swift "a songwriting savant with an intuitive gift for verse-chorus-bridge architecture. If she ever tires of stardom, she could retire to Sweden and make a fine living churning out hits for Kelly Clarkson and Katy Perry." Fearless resides at No. 1 for more than six straight weeks and earns Swift Album of the Year at the Academy of Country Music awards.
2009: March
Taylor Takes on Rolling Stone
Swift, 19, gets candid on the cover of Rolling Stone, where she says of sex, "I feel like whatever you say about whether you do or don't, it makes people picture you naked. And as much as possible, I'm going to avoid that." Of her love (and breakup) songs, she adds, "I love love. I love studying it and watching it. I love thinking about how we treat each other, and the crazy way that one person can feel one thing and another can feel totally different."
September 13
Swift's VMA Diss
While accepting the MTV VMA for best female video, Swift is interrupted by Kanye West, who comes onstage and takes issue with her win. "Beyoncé had one of the best videos of all time," he says. After, celebs like Kelly Clarkson and even President Obama take West to task. He eventually phones Swift to apologize.
October
Taylor Squared
After Taylor Lautner is snapped at Swift's concerts–including one in which she runs offstage to give him a hug–the Valentine's Day costars attend a hockey game together in Los Angeles. Pressed about their relationship, Swift says, "He's an amazing guy and we're really close."
November 11
Sweeping the CMAs
It's a monumental night for Swift at the 2009 Country Music Awards, where she takes home four awards, including album of the year for Fearless and entertainer of the year. "I will never forget this moment because in this moment everything I have ever wanted has just happened to me," the 19-year-old says after becoming the youngest-ever winner of the CMA's top trophy.
2010: January 31
Grammy Girl
Eight-time Grammy nominee Swift takes home four awards, including the coveted album of the year. "I just hope that you know how much this means to me – that we get to take this back to Nashville," she says in her acceptance speech. At the ceremony, the country hitmaker also scores best country song, best female country vocal performance and best country album.
February 12
Swift Goes Hollywood
Swift makes her big-screen debut in the star-studded movie Valentine's Day with former flame Taylor Lautner. The romantic comedy, which also costars Julia Roberts and Ashton Kutcher, debuts at the top of the box office. "She may win something as an actress very soon," director Garry Marshall predicts of the acting newcomer. "I think she's got a career."