"Magic", which to give proper credit was written by Ben Fold Five's drummer, Darren Jessee. It's particularly touching if you've ever lost someone to a painful disease.
"Fred Jones, Part 2" is an extremely sad song, which deals with the unfairness of a good man fading away, unremarked on by the universe at large.
"The Luckiest." That's love, love, love.
"Don't Change Your Plans" is another one.
"Kylie From Connecticut" is a great one off his new album that can really get you, especially the heartbreaking cry of the chorus.
And then there's "Cigarette", which packs a heck of a lot of tragedy into a Single Stanza Song. Even moreso when you find out it's taken verbatim from a newspaper clipping. Man, can Ben Folds write an incredibly sad song when he wants to.
"Belinda" from Lonely Avenue. Oh, God, "Belinda"...
Belinda, I love you, Don't leave me, I need you.
The chorus of On Being Frank just sounds hopelessly lost.
And I don't know where I might be going I rode the wind, the wind stopped blowing, Left me on the roadside, thumbing home. But home, for me, was always someone else, you know? How shadows always fall when the sun goes down....
"Still" from the Over the Hedge soundtrack, a somber reminder than, whether we like it or not, change is going to happen.
The actual album version is even worse. It's about three or four minutes longer and has a few extra verses that are even more heartbreaking than the version from the movie.