18. "Fearless" (2008)
Oh Fearless, it's easy to take you for granted sometimes. The first time I heard her sophomore record (the record company literally played it over the phone for me because they were so afraid of it leaking) I thought, "Holy cats, this is a perfect pop album. She'll never top this." Then she topped it four times in a row, to the point where it's one of history's most curiously overlooked perfect pop albums. The title anthem gathers so many of her favorite tropes in one chorus – rain, cars, fancy dresses, boys who stare at her while driving instead of watching the damn road, shy girls posing as brave and faking it till they make it – and builds up to a swoon.
Best line: "You're just so cool, run your hands through your hair / Absent-mindedly making me want you."