I'll admit to it:
Iris, by the Goo Goo Dolls, gets me misty-eyed.
The Rain King, by Counting Crows, sort of reminds me of a friend whom I've not seen in almost ten years. Yeah, I miss you, Goldenrod, wherever you are.
The Lady of Shallott, and The Highwayman, sung by Loreena McKennitt. Because, seriously. Just. Just listen to them and try to stay dry. If you do, I declare you heartless.
Serafina, by A Covenant of Thorns. 'Cause I'm a sap.
Song to the Siren, This Mortal Coil. Not always, but often.
Airships, VNV Nation. It makes me think, for some reason, of a friend who is no longer here, a friend who I feel I wronged, and never got to apologize to.
Hm. This list is far too long.