Whether it's a LonelyPianoPiece or [[LyricalDissonance super depressing lyrics set to a happy tune]], Ben Folds knows how to hit listeners in the gut.

* Technically Darren Jessee's song, but "Magic" by Ben Folds Five is particularly touching if you've ever lost someone to a painful disease.
* "The Luckiest." It's love incarnate.
* "Don't Change Your Plans" is another one.
* "Kylie From Connecticut." That chorus is ''heartbreaking.''
* "Cigarette," which packs a heck of a lot of tragedy into a SingleStanzaSong. Worse, the lyrics are taken verbatim from a newspaper clipping about a man who wanted to divorce his wife because her brain tumor made her "become a different person."
* Then there's the unofficial SequelSong, "Fred Jones, Part 2," about the titular character, an elderly but dedicated newspaper employee, being forced into retirement, fading away, unremarked on by the universe at large.
* "Brick," especially if you know the very real backstory behind it.[[note]]It's about how his high school girlfriend had to get an abortion.[[/note]] There's a reason it's Ben Folds Five's most popular song.
* "Late," his eulogy to the late Music/ElliottSmith. It doesn't say much about the man himself, as Ben didn't know him that well personally, but it says more than enough about why he was important.
--> ''Elliot, man, you played some fine guitar''
--> ''And some dirty basketball''
--> ''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.
* "Picture Window." What sick individual tells their child that they can't afford the hope that she'll get better?
* "Evaporated" is a pretty strong tear magnet.
* "Carrying Cathy," especially if you know someone who's suicidal or eventually committed suicide.
* "SMOKE!"
* "From Above." [[LyricalDissonance Don't let the catchy tune fool you]].
--> 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.
* Dear 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 ''WesternAnimation/OverTheHedge'' soundtrack, a somber reminder than, whether we like it or not, change is going to happen. And the extended version on the album is even worse.
* "Landed" can be this for anyone who realized too little too late that they were the victim of an abusive relationship, and that you ended up shunning your true loved ones as a result.