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Swift went to her first Grammys in 2008, but only as a spectator. In 2009, however, she took the stage to perform an acoustic duet with fellow rising star Miley Cyrus. The two showed off their very country roots. Swift was not nominated for any awards that year.
The video quality is poor, but so is the singing. This performance was met with major criticism. It's clear Swift's come a long way since this cringe-worthy duet.
The performance started with an acoustic version of "Today Was a Fairytale." Then, Swift was joined onstage by Stevie Nicks for out-of-key renditions of "Rhiannon" and "You Belong With Me."
Regardless of the iffy live vocals, Swift won Album of the Year for Fearless. She beat out Beyoncé, The Black Eyed Peas, Dave Matthews Band, and Lady Gaga. She went on to win three more Grammys that night: Best Country Album, Best Country Vocal Performance, and Best Country Song.
At the 54th Grammys, Swift took home two awards for her song "Mean" before performing it live. Swift had to make up for her rocky performance with Nicks the previous year, and said her motivation for the song came from the critics of her 2011 performance.
Swift opened the Grammys in 2013 with a playful circus routine that many suspected featured a call-out to her ex Harry Styles. Similar speculations circulated again this year after the release of her "Out of the Woods" music video.
She also won a Grammy for Best Song Written for Visual Media for "Safe & Sound," featuring The Civil Wars.