Swift's second studio album, Fearless, was released on November 11, 2008.[66] 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[52] and number one in Australia.[67] "You Belong with Me" was the album's highest-charting single on the Billboard Hot 100, peaking at number two.[68] All five singles were BillboardHot Country Songs top-10 entries, with "Love Story" and "You Belong with Me" peaking at number one.[69] Fearlessdebuted at number one on the Billboard 200 and was the top-selling album of 2009 in the U.S.[70] The Fearless Tour, Swift's first headlining concert tour,[71] grossed over $63 million.[72] Journey to Fearless, a three-part documentary miniseries, was aired on television and later released on DVD and Blu-ray.[73] Swift also performed as a supporting act for Keith Urban's Escape Together World Tour in 2009.
That year she won five American Music Awards, including Artist of the Year and Favorite Country Album.[81] Billboard named her 2009's Artist of the Year.[82] The album ranked number 99 on NPR's 2017 list of the 150 Greatest Albums Made By Women.[83] At the 52nd Annual Grammy Awards, Fearless was named Album of the Year and Best Country Album, and "White Horse" was named Best Country Song and Best Female Country Vocal Performance. Swift was the youngest artist to win Album of the Year.[a] 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 honor.