For fun...
Top whatever number of songs with the most unexpectedly depressing lyrics.
That is, songs where you have to listen to the whole song before you realize just how depressing it is, like, say "Cat's in the Cradle" or "(don't you know that you are a) Shooting Star", as opposed to, say, "Yesterday", where you know what's up from the start, or, say, songs with music that's exceedingly depressing even without any words (most stuff by The Cure, for example...)
So, yeah, to start the ball rolling:
"Cat's in the Cradle"
"Shooting Star"
(I'd probably think of more, but those are the two that I've overheard on the radio recently)
That is, songs where you have to listen to the whole song before you realize just how depressing it is, like, say "Cat's in the Cradle" or "(don't you know that you are a) Shooting Star", as opposed to, say, "Yesterday", where you know what's up from the start, or, say, songs with music that's exceedingly depressing even without any words (most stuff by The Cure, for example...)
So, yeah, to start the ball rolling:
"Cat's in the Cradle"
"Shooting Star"
(I'd probably think of more, but those are the two that I've overheard on the radio recently)