When I was in college – and infinitely more dramatic than I am now (no seriously) – I used to make a lot of mix CDs.
I still have ’em, actually. And almost every single one of them is filled with songs that are OK to listen to when you’re sad but really just kind of re-enforces everything you’re already feeling because that song is exactly your situation.
I’ve gotten over that – thank God – and now when I’m sad I don’t listen to depressing songs, I just take a nap.
But if I had to pick one now, I’d say “Landslide.” Stevie Nicks version, then Dixie Chicks, then Glee.