32. Taylor Swift, Fearless
How much heartbreak can anyone cram into 18 years? If you’re Taylor Swift, a lot. Boys are to this Nashville blonde what booze is to Homer Simpson: the cause of, and solution to, all of life’s problems. The kicky twang pop on her second album shows she’s country by accident as much as by design; if her parents had moved to L.A. instead of Tennessee, she could have been Avril Lavigne. But Avril never wrote a song as smart as “That’s the Way I Loved You.”
Download “You Belong With Me,” “Fearless,” “That’s the Way I Loved You”