Swift carried out her first headlining tour in support of Fearless. As part of the 105-date Fearless Tour, Swift played 90 dates in North America, six dates in Europe, eight dates in Australia and one date in Asia.^[84] She sang a cover of Justin Timberlake's "What Goes Around... Comes Around" nightly, intertwined with her own "You're Not Sorry".^[85] Swift invited John Mayer, Faith Hill and Katy Perry to perform one-off duets with her at various dates during the North American tour, while Justin Bieber, Kellie Pickler and Gloriana were the support acts.^[86] The tour was attended by more than 1.1 million fans and grossed over $63 million.^[87] Taylor Swift: Journey to Fearless, a concert film, was aired on television and later released on DVD and Blu-ray.^[88] Swift also performed as a supporting act for Keith Urban's Escape Together World Tour.^[89] In addition to tour dates, the singer paid tribute to a number of fellow artists in televised performances. She performed a cover of Alan Jackson's "Drive (For Daddy Gene)" at the CMT Giants: Alan Jackson event, took part in a joint, televised concert with rock band Def Leppard in Nashville, and performed a cover of George Strait's "Run" at a televised ACM event honoring Strait as the Artist of the Decade.^[90] Swift sang her song "Fifteen" with Miley Cyrus at the 51st Grammy Awards and performed a self-penned rap skit with T-Pain at the CMT Awards.^[91] Swift also recorded a number of side-projects. She released a cover of Tom Petty's "American Girl" through Rhapsody in 2009^[92] and made her stage entrance to Petty's recording of the song until 2013.^[93] She contributed backing vocals to John Mayer's "Half of My Heart", a single featured on his fourth album.^[94] She co-wrote and recorded "Best Days of Your Life" with Kellie Pickler^[95] and co-wrote two songs for the Hannah Montana: The Movie soundtrack – "You'll Always Find Your Way Back Home" and "Crazier" – withMartin Johnson and Robert Ellis Orrall, respectively.^[96] Swift also provided vocals for Boys Like Girls's "Two Is Better Than One", written by Martin Johnson.^[97] She contributed two songs – including "Today Was a Fairytale" – to the Valentine's Day soundtrack^[98] and recorded a cover of Better Than Ezra's "Breathless" for the Hope for Haiti Now album.^[99]

Swift performing in Los Angeles during the Fearless Tour in 2010

Swift became the first country music artist to win an MTV Video Music Award when "You Belong with Me" was named Best Female Video in 2009.^[100] Her acceptance speech was interrupted by rapper Kanye West, who had been involved in a number of other award show incidents.^[101] In the event's press room, Swift, a fan of West's music,^[102] denied having "any hard feelings" towards him.^[103][104] The incident received much media attention and inspired many Internet memes.^[105] A few days later, Swift told an interviewer that West offered her a personal apology, which she accepted: "He was very sincere."^[100] She refused to discuss the incident in subsequent interviews so as not to make a "bigger deal" of it: "It happened on TV, so everybody saw what happened ... It's not something I feel like we need to keep talking about."^[106] It has been said that the incident and subsequent media attention turned Swift into "a bona-fide mainstream celebrity."^[107]