47. Fiona Apple, When The Pawn... (Clean Slate/Epic, 1999)

A little crazy, a little pretentious (I'll refrain from listing the entire 90+ word title), a little genius. She recorded her fantastic debut, Tidal, when she was just 19; this follow-up, released three years later, is a quantum leap in every imaginable way except for one thing: while accessible, the songs don't immediately grab you. It takes more than a few listens for their complexities to sink in, like the stop-and-start compulsiveness of "Fast as You Can" or the whisper-to-a-scream dynamics of "Limp". When they do, of course, they're unshakable. Consequently, this produced no hits (not even "Paper Bag", Beatles-esque in every best way) but it stands as a frightening, exhilarating puzzle--not least because Apple wears her neuroses on her sleeves but doesn't shy away from trying to make sense of them.