Amanda Palmer/Tear Jerker

Amanda Palmer, be it with or without The Dresden Dolls, can make some pretty sad songs.

Let's talk about the Dresden Dolls for a moment. Even the name is depressing. Highlights include about ninety percent of their debut album (listen to the lyrics of "Half-Jack" closely and marvel at what you're hearing), "Delilah," "Sing" (which manages to be both one of the most somber songs ever written and one of the most triumphant), and "Me & the Minibar," the last line of which will make your jaw drop with depression overload. Imagine something so depressing you can't help but laugh and dial it back exactly enough to keep it completely serious.
"The Point of it All" from Amanda Palmer's solo album, Who Killed Amanda Palmer? "But no one can stare at the wall as good as you, my baby doll/and you're aces for coming along/you're almost human, after all..."
- Obnoxious title aside, "Strength Through Music" can still make some people bawl. How many songs are there about school shooters? How many artistic works in any medium that make you pity them?
  - Made somewhat narmful if you know that the sample in the beginning is from Stringberg and Helium, however.
- The cover of "What's the Use of Wond'rin'?" puts the song in a whole new (and disturbing) perspective.
- Pretty much the entire album of Who Killed Amanda Palmer? counts. It was produced by Ben Folds, for whom this trope may be an actual superpower.
"Trout Heart Replica" a song Amanda wrote while on tour after seeing a dead trout's still beating heart, at several shows when she played this, the entire audience was in tears.
- Named after a Captain Beefheart song, fyi.
This blog post, written in the aftermath of the 2011 Christchurch earthquake. If Mrs. Palmer's tour was on time, she would have been right at ground zero. The tone, the content, the links to the NZ Red Cross, the poem at the end... well, it can really get you sobbing.
Off of the new collaboration, 8in8, we have "Because the Origami," a duet between Ben Folds and her about a runaway son. Grab a box of tissues, and take a listen.
The final verse of Amanda's parody of Friday.