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"Fifteen" with Taylor Swift (2009)

Miley sat in with fellow country-pop prodigy Taylor Swift for a performance of "Fifteen" at the 2009 Grammy Awards, showing off her twangy voice and wiser-than-her-years delivery while providing counterpoint vocals on Swift's tale of second-hand heartbreak. (She also introduced Swift as her "best friend" in the award-presentation spiel that followed.)