Swift's latest studio album, Fearless, was released in the United States on November 11, 2008. The album debuted at #1 on the Billboard 200 Album Chart. Its sales of 592,304 was the highest debut of any country artists in 2008. This is also the largest opening U.S. sales week in 2008 by a female artist in all genres of music, and the fourth biggest overall behind Lil Wayne, AC/DC and Coldplay. Its lead single "Love Story" became a hit on both the country and pop charts.

During the first week of release, more than 129,000 of Swift's sales were sold digitally. This gives Swift the best online start for any country album in history. It also makes Swift the fourth biggest week for a digital album since Nielsen SoundScan began tracking them in 2004. Through its eighth week of release, Fearless has sold more than 338,467 paid downloads, making it the bestselling country album in digital history. In second place, it is Swift's debut Taylor Swift with sales of 236,046 downloads as of April 18, 2009.

In its debut week, seven songs in total on Fearless were charted on Billboard Hot 100, tying Swift with Hannah Montana for the most by a female artist in a single week. With "White Horse" charted at #13, this gave Swift her sixth top 20 debut of 2008, a calendar year record for any artist in the history of the Billboard Hot 100. Of the 13 tracks on Fearless, 11 have already spent time on the Hot 100.

"Change", a song from the album, was selected as part of a soundtrack supporting Team USA's efforts in the 2008 Summer Olympics. The song was also featured as part of the soundtrack of NBC's broadcast package of the Olympics. She also released the lead single from the album, "Love Story", on September 12, 2008. The song is accompanied by a music video that is based on Romeo and Juliet. The song has reached number 2 on iTunes Store Top Downloaded Songs and number four on the Billboard Hot 100. Fifteen weeks after being added to pop radio, "Love Story" also became the first country crossover recording to hit number one on the Nielsen BDS CHR/Top 40 chart in the 16-year-history of list, as well as number one on the Mediabase Top 40 Chart. The second single from Fearless, "White Horse", was released on December 8, 2008. The music video for the song premiered on CMT on February 7, 2009. Though it missed the #1 spot on Billboard's Hot Country Songs as of the week April 11, 2009, "White Horse" claimed the #1 spot atop the USA Today/Country Aircheck chart (powered by Mediabase) in that week. "Forever & Always", another song from the album, was based on Swift's relationship with singer Joe Jonas.

Swift is Billboard's Top Country Artist and Hot Country Songwriter of 2008; she is also country music's best-selling artist of 2008.

Swift ranked seventh on Nielsen SoundScan Canada's top-10 selling artists across all genres in 2008. Fearless and Taylor Swift took the #1 and #2 slots on 2008 Year-End Canadian Country Albums Chart.

Swift sang the Star-Spangled Banner at game three of the World Series in Philadelphia on October 25, 2008.

On January 10, 2009, Swift made her first musical guest appearance on Saturday Night Live, making her the youngest country singer to appear as a musical guest on the show in its 33-year run. Swift's show achieved SNL’s highest adult 18-49 rating and overall viewer total since the November election (in 2008). It was tied for the #7 rating of that week among all broadcast and cable entertainment programs on all networks and outscored all its telecasts of last season in 18-49 and total viewers.

On February 8, 2009, Swift performed her song "Fifteen" with Miley Cyrus at the 51st Grammy Awards.

Since the release of Swift's second album, Fearless, she has released one new song "Crazier" for the soundtrack of the feature film Hannah Montana: The Movie.

At the 44th Annual Academy of Country Music Awards, Swift picked up Album of the Year honors as a performer and producer for Fearless. She is the youngest artist in history to win Album Of The Year award. Swift was also awarded the Academy's Crystal Milestone Award, given for Outstanding Achievement in Country Music. The Academy lauded her for career achievements including selling more albums in 2008 than any other artist in any genre of music, the breakthrough success of her debut album (which spawned five Top 10 hits, more than any in history for a female artist's debut CD), and the worldwide crossover success of her #1 single "Love Story". The Academy also cited Swift's contribution to helping country music attract a younger audience.

As of late April 2009, Swift has sold more than 14 million downloads, as well as three Gold Mobile Ringtones.

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