Raise Your Glass by Pink. I actually like just about everything by Pink.
#12 - A Song No One Would Expect Me to Love
Heaven (Where True Love Goes) by Yusuf Islam. Now, I love the Cat, but generally I'm not into denominational music or denominational anything. I just kind of close my ears at the points where it talks about being saved and knowing His name, and this song really is beautiful.
#13 - A Song that Describes Me
Only Happy When It Rains by Garbage. This probably described me more when I was young, maybe between 16-24--back when I had time and energy to enjoy it when things were complicated. Still, great memories about this song (this whole album, really).
#14 - A Song I Used to Love But Now I Don't
Let the Drummer Kick by Citizen Cope. I still kind of like this song, particularly the opening, but I REALLY don't like the stream of "tion" words masquerading as lyrics. But, it's still a good hook.
#15 - A Song From My Favorite Album
High and Dry by Radiohead. Best album, and one of the best bands. Seriously, this whole record is just perfect.
#16 - A Song For Angry Times
Positive Tension by Bloc Party. We saw these guys at the Orpheum in Boston and they were awesome. I listened to this song a lot when I lived in Boston, and I felt angry a lot in Boston, so I suppose the connection forged itself.