Steven Fiore – Why Do You Waste Your Breath? While not his saddest song, it’s a pretty sad song but a pretty, sad song. Someone who won’t stop apologizing to him but to everyone else, acts like they’ve done nothing wrong. Perfect for the holiday season.
Young Alumni – Styrofoam Airplane Also perfect for the holiday season—a song about escapism. After the last song, you’ll probably need this one.
Yeasayer – Ambling Alp If you read my Yeasayer article, I needn’t say more. If you've haven’t, go do it. If you have and still haven’t checked out this song, may Cthulhu have mercy on your soul.
The Morning Benders – Excuses (Yours Truly Session) Young love—so beautiful…