Radiohead - Street Spirit (Fade Out) (Most Radiohead songs are depressing, I find this one more so.)
Jeff Buckley - Hallelujah
And even though the message of it isn't depressing, Wires by Athlete is pretty depressing to me.
Oh, and Bobby McFerrin - Don't worry, be happy
EDIT:
Bryan Adams - Sound The Bugle. Can't believe I forgot that one.
Jeff Buckley - Hallelujah
And even though the message of it isn't depressing, Wires by Athlete is pretty depressing to me.
EDIT:
Bryan Adams - Sound The Bugle. Can't believe I forgot that one.