2008

Taylor Swift

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

Taylor Swift

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."

Taylor Swift

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.

Taylor Swift

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."

Taylor Swift

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

Taylor Swift

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.

Taylor Swift

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."

Taylor Swift

October

Taylor Kisses & Tells

With the release of her third album Speak Now (which sells more than a million copies in a week and helps her win the entertainer of the year ACM award!), Swift nabs her first PEOPLE cover, in which she dishes on the guys who inspired her new music. "I will say everything in my music," says the 20-year-old country star. "Sometimes when things impact you so intensely, it takes writing a song to get over them."

Taylor Swift

October

Taylor's Hollywood Hookup

After attending Saturday Night Live together, Swift, 20, is spotted having brunch with 29-year-old actor Jake Gyllenhaal in Brooklyn the next day. "They're cute together," a source close to the actor tells PEOPLE, before the pair hit the singer's hometown of Nashville during their brief romance.

Taylor Swift

December

Easy, Breezy, Beautiful

Joining the ranks of Drew Barrymore, Ellen DeGeneres and Queen Latifah, Swift becomes the latest face of CoverGirl. "I have admired many of the CoverGirls since I was a little girl… great artists and actresses who are confident and still themselves," the singer says in a press release. "It's like a dream come true to be a part of the future of CoverGirl."

Photo Credits

BIOGRAPHY (top to bottom): amazon.com; Courtesy of Rolling Stone; Kevin Mazur/WireImage; Andrew D. Bernstein/Getty; Rick Diamond/Getty; Mark Terrill/AP; INF; Swarbrick/INF; Courtesy CoverGirl

Edited by Julia Wang

Taylor Swift

Celebrity Central / Top 25 Celebs

 

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