If you’re looking for music that will result in a good cry, The Quietus has this list of sad songs–or at least songs that make their writers cry. There’s some weird ones here–“Common People” by Pulp? Really?–but there are plenty of honest-to-god tearjerkers.
I’d like to add one more. How can anyone listen to “The Band Played Waltzing Matilda” by The Pogues and not get all verklempt?
(Thanks to Fouad for the link.)