I am not a Fiona Apple fan. I don't have anything against her, you understand. It's just that nothing she's recorded has really leapt out at me, from the very beginning to the present day, with one exception: the title track from her 2005 LP Extraordinary Machine.
The first time I heard this was probably December of 2005. I was in Maine, in the backseat of a friend's car on the way to do some skiing, and I couldn't believe it was Apple when he told me it was. He tried to play the rest of the LP for us that ride, and maybe he did a little, but I know I had him play "Extraordinary Machines" over and over, as well.
This song is magical. It's like some alternate-dimension version of what pop music on Earth sounds like. The orchestration, the style of her voice, the lyrics, the rhythm of the vocal part: it's all so distinct, not only from other popular music, but from Apple's other music. The rest of LP reaches for this quality, but never quite gets there. If the top-100 list were to be trimmed to only ten, this track would almost definitely remain. It's special.