* "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.
* "[[http://info.benfolds.org/FredJonesPart2Lyrics 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.
* "[[http://www.youtube.com/watch?v=5CCUtcnexEY 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 "[[http://www.songmeanings.net/songs/view/33/ Cigarette]]", which packs a heck of a lot of tragedy into a SingleStanzaSong. 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.
* [[http://www.youtube.com/watch?v=Wt5EHAqhR1c "Brick"]]. It's especially horrible if you know the [[http://en.wikipedia.org/wiki/Brick_%28song%29 backstory.]]
* Not to mention Ben Folds' simple, personal lament to Elliott Smith, "Late". *Sigh* "The songs you wrote... got me through a lot, just wanna tell you that... But it's too late."
* "Still Fighting it" is a song about how teenage years are hard. Depends on your interpretation: others might read it as an ode to parental failure.
* "[[http://www.youtube.com/watch?v=EAQhLJmrGS4 Picture Window]]"
* "Evaporated" is a pretty strong tear magnet.
* [[http://www.youtube.com/watch?v=hP0mFcHek9M Carrying Cathy.]]
* Maybe it's just me, but I find [[http://www.youtube.com/watch?v=X5peqCDJi0A From Above]] to be depressing as hell. [[LyricalDissonance Don't let the catchy tune fool you,]] just read the lyrics without any musical influence:
--> It's so easy [[TitleDrop from above,]]
--> You can really see it all,
--> People who belong together
--> Lost and sad and small.
--> But there's nothing to be done for them,
--> It doesn't work that way.
--> Sure we all have soul mates, but
--> We walk past them everyday.
** And the music video doesn't help either.
* "Belinda" from ''Lonely Avenue''. Oh, God, "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 OverTheHedge 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.