Tom Waits - "Christmas Card from a Hooker in Minneapolis"
For those of you who don't always anticipate the holiday season with a whole lot of enthusiasm, remember: it could be worse. You could be pregnant. In prison. With lawyers to pay. Tom Waits' original version of this song is chilling, but I've always thought Neko Case's vocals bring the destitution home in a way that Waits' gravelly Oscar-the-Grouch growl just can't (song posted after the jump):
Aretha Franklin - "Blue Holiday"
Yeah, being single during the holidays sucks...
Soul Searchers - "Christmas in Vietnam"
...but as depressing topics go, it's pretty hard to top spending Christmas at war.
This song is such a downer, I haven't even been able to find a video of it -- probably because listening to a song that begins with the line, "I was thinking I could clean up for Christmas" is similar to watching a movie like "Boys Don't Cry": worthwhile, but not an experience you care to repeat on a regular basis.