79. "Crazier" (2009)
Her ballad from Hannah Montana: The Movie, snagging her a cameo in the film. (But the highlight of the soundtrack will always be "Hoedown Throwdown.") This is where Taylor and Miley crossed light sabers – although they'd meet again. Great title, too – even Taylor might probably admit Miley had her beat in this department, at least until the "Blank Space" video.
Best line: "Every sky was your own kind of blue."