2008–2010: Fearless and acting debut

Swift at the 2009 premiere of Hannah Montana: The Movie. She had a cameo appearance in the
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film and wrote two songs for its soundtrack.

Swift's second studio album, Fearless, was released on November 11, 2008, in North
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America, and in March 2009, in other markets. Critics lauded Swift's honest and
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vulnerable songwriting in contrast to other teenage singers. Five singles were released
in 2008 through 2009: "Love Story", "White Horse", "You Belong with Me", "Fifteen", and
"Fearless". "Love Story", the lead single, peaked at number four on the Billboard Hot 100
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and number one in Australia. It was the first country song to top Billboard's Pop
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Songs chart. "You Belong with Me" was the album's highest-charting single on the
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Billboard Hot 100, peaking at number two, and was the first country song to top
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Billboard's all-genre Radio Songs chart. All five singles were Hot Country Songs top-10
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entries, with "Love Story" and "You Belong with Me" topping the chart. Fearless
became her first number-one album on the Billboard 200 and 2009's top-selling album in
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the U.S. The Fearless Tour, Swift's first headlining concert tour, grossed over $63
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million. Journey to Fearless, a three-part documentary miniseries, aired on television
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and was later released on DVD and Blu-ray. Swift also performed as a supporting act
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for Keith Urban's Escape Together World Tour in 2009.
In 2009, the music video for "You Belong with Me" was named Best Female Video at the
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MTV Video Music Awards. Her acceptance speech was interrupted by rapper Kanye
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West, an incident that became the subject of controversy, widespread media attention,
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and many Internet memes. That year she won five American Music Awards, including
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Artist of the Year and Favorite Country Album. Billboard named her 2009's Artist of the
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Year. The album ranked number 99 on NPR's 2017 list of the 150 Greatest Albums Made
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By Women. She won Video of the Year and Female Video of the Year for "Love Story" at
the 2009 CMT Music Awards, where she made a parody video of the song with rapper
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T-Pain called "Thug Story". At the 52nd Annual Grammy Awards, Fearless was named
Album of the Year and Best Country Album, and "White Horse" won Best Country Song
and Best Female Country Vocal Performance. Swift was the youngest artist to win Album
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of the Year. At the 2009 Country Music Association Awards, Swift won Album of the
Year for Fearless and was named Entertainer of the Year, the youngest person to win the
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honor.
Swift featured on John Mayer's single "Half of My Heart" and Boys Like Girls' single "Two
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Is Better Than One", both of which she co-wrote. She co-wrote and recorded "Best
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Days of Your Life" with Kellie Pickler, and co-wrote two songs for the Hannah Montana:
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The Movie soundtrack—"You'll Always Find Your Way Back Home" and "Crazier". She
contributed two songs to the Valentine's Day soundtrack, including the single "Today Was
a Fairytale", which was her first number-one on the Canadian Hot 100, and peaked at
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number two on the Billboard Hot 100. While shooting her film debut Valentine's Day
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in October 2009, Swift dated co-star Taylor Lautner. In 2009, she made her television
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debut as a rebellious teenager in an CSI: Crime Scene Investigation episode. She
hosted and performed as the musical guest on Saturday Night Live; she was the first host
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to write their own opening monologue.