2008 to 2010 :

                   Fearless and acting:
Swift's second studio album Fearless was released on November 11, 2008.The lead single, "Love Story", was released in September 2008. It peaked at number four on the Billboard Hot 100 and number one in Australia.Four more singles were released throughout 2008 and 2009: "White Horse", "You Belong with Me" "Fifteen" and "Fearless". "You Belong with Me" was the album's highest-charting single on the Billboard Hot 100, peaking at number two. The album debuted at number one on the Billboard 200 and was the top-selling album of 2009 in the United States. The album received promotion from Swift's first concert tour, the Fearless Tour, which grossed over $63 million.Taylor Swift: Journey to Fearless, a concert film, was aired on television and later released on DVD and Blu-ray. Swift also performed as a supporting act for Keith Urban's Escape Together World .
In 2009, the music video for "You Belong with Me" was named MTV Video Music Award for Best Female Video.Her acceptance speech was interrupted by rapper Kanye West. The incident was the subject of controversy and frequent media attention, resulting in many Internet memes. James Montgomery of MTV argued that the incident and subsequent media attention turned Swift into "a bona-fide mainstream celebrity". Also that year, she won five American Music Awards, including Artist of the Year and Favorite Country Album. Billboard named her 2009's Artist of the Year.The album ranked number 99 on NPR's 2017 list of the 150 Greatest Albums Made By Women.

At the 52nd 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 ever to win Album of the Year. During the ceremony, Swift sang "You Belong with Me" and "Rhiannon" with Stevie Nicks. Her vocal performance received negative reviews and a media backlash. Jon Caramanica of The New York Times found it "refreshing to see someone so gifted make the occasional flub" and described Swift as "the most important new pop star of the past few years". Swift became the youngest ever artist to be named Entertainer of the Year by the Country Music Association.Fearless also won the Association's Album of the Year award.

Swift contributed backing vocals to John Mayer's "Half of My Heart"a single featured on his fourth album, Battle Studies (2009).She co-wrote and recorded "Best Days of Your Life" with Kellie Pickler, and co-wrote two songs for the Hannah Montana: The Moviesoundtrack—"You'll Always Find Your Way Back Home" and "Crazier". Swift also provided vocals for Boys Like Girls' "Two Is Better Than One". She contributed two songs to the Valentine's Day soundtrack, including "Today Was a Fairytale", which became her first number one on the Canadian Hot 100 chart.While filming her cinematic debut Valentine's Day in October 2009, Swift began a romantic relationship with co-star Taylor Lautner, but they broke up later that year.The romantic comedy, released the following year, saw her play the ditzy girlfriend of a high school jock, a role in which Los Angeles Times found "serious comedic potential". In a scathing review, the critic for Variety deemed her "entirely undirected", arguing that "she needs to find a skilled director to tamp her down and channel her obviously abundant energy".



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