Originally Posted by Captain Awesome

You know there's more to rap than "sad songs" and "party songs". Anyway, I wouldn't class rhymefests bullet as a sad song you seem to be talking about songs with meaning rather than the usual pop rap nonsense.

I'd suggest these (from the top of my head);

Cuban Link - letter to pun (a tribute to big pun, whom cuban link was good friends with)
Fort Minor - the hard way
Masta Ace - dear diary
Non Phixion - say goodbye to yesterday
Jedi Mind Tricks - black winter day
Bliss n Eso - bullet and a target
Hilltop Hoods - fifty in five (a recap of the last fifty years in five minutes).
Lowkey - rise and fall
Pez - heavenly (not so much a sad song, just a beautiful track dedicated to his parents).
Ludacris - runaway love
Rhyme Asylum - lost
Zion I & The Grouch - make u fly
Proof - kurt kobain
Respek BA - hope
Tech N9ne - the rain
Royce 5'9 - life
Xdash - Foolish Games (I actually know the guy who produced this. well not in real life but through forums from a long time ago lol).