Taylor Swift Embarks on First Headlining Tour (April 2009)
Following the November 2008 release of sophomore album "Fearless," Swift made a big move in becoming the touring phenom she is today by announcing her first-ever headlining tour, a 52-city trek that began in April 2009. Eventually, the Fearless tour would make its way across the U.S., United Kingdom, Canada, Australia and even Japan before concluding in June 2010 with a grand total of 105 shows and a gross of $62.6 million, according to Billboard Boxscore. Long before her "Speak Now" global dominance, Swift was becoming one of country music's most accomplished road warriors.
Kanye West Interrupts Swift's VMA Speech (September 2009)
One of the defining moments of Taylor Swift's career had nothing to do with the country star's own actions: at the 2009 MTV Video Music Awards, Kanye West jumped onstage during Swift's acceptance speech for Best Female Video, grabbed her microphone and told the crowd that Beyonce's "Single Ladies" clip was more worthy of the award. The tirade left Swift stunned onstage, and West was forced to leave New York's Radio City Music Hall shortly after. The unexpected meeting between the rapper and country singer resonated throughout pop culture long after that September night: West effectively disappeared for months and issued Twitter apologies before triumphantly returning in 2010 with "My Beautiful Dark Twisted Fantasy," while Swift deemed the rapper an "Innocent" in a song on "Speak Now."
Taylor Swift Makes History at CMA Awards (November 2009)
At 19 years old, Swift became the youngest Entertainer of the Year winner at the Country Music Association Awards when she first took home the top prize in 2009. Celebrating the year in which "Fearless" became a blockbuster hit, the CMAs graced Swift with trophies for Female Vocalist of the Year, Music Video of the Year for her "Love Story" clip, and Album of the Year for "Fearless." "I'll never forget this moment, because at this moment everything that I ever wanted has just happened to me," a tearful Swift told the crowd. After ceding the Entertainer of the Year award to Brad Paisley in 2010, Swift regained the top prize at last year's ceremony.