I'm relistening to my soundtrack album of Hedwig and the Angry Inch. These songs are all superb, and a number of them are very emotionally engaging. "Wicked Little Town," "Midnight Radio," and "Wig in a Box" really get to me. Another melancholy song that I like a lot is "Long Grift" - it packs an awful lot of pain and disillusionment in a few words and chords. Here is an excerpt:

I'm just another john you've gypped,
another sucker stiffed,
a walk on role in the script
to your long, long grift.
The love that had me in your grip
was just a long, long grift.