59. "You Belong With Me" (2008)
One of her most pop-friendly early hits, singing in the role of a high school geek crushing on her best guy friend. When he comes out in college, they'll have a few laughs about this. (And never let us forget the wisdom of Alicia Silverstone in Clueless: "Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie."
Best line: "She wears high heels, I wear sneakers/She's cheer captain, and I'm on the bleachers."