- Pretty much all of the album Electro-Shock Blues, especially "Dead of Winter" and the final track "P.S. You Rock My World" ("...everyone is dying, and maybe it's time to live"). The whole album may be THE most depressive album ever, and is his best work.
- "Last Stop: This Town". It helps if you know beforehand that it's about the suicide of the songwriter's sister.
"What if I was not your only friend in this world? Will you take me where you're going if you're never comin' back?"
- "Somebody Loves You" is another one.
- Then there is "I Need Some Sleep", an extremely sad song.
- "Things The Grandchildren Should Know" is another big one. The song can hit really hard, in particular this line:
"I do some stupid things, but my heart's in the right place, and this I know."
- "Flower", "Manchild" (both from Beautiful Freak), "Climbing to the Moon", "Railroad Man", "If You See Natalie", "I'm Going to Stop Pretending that I Didn't Break Your Heart", "A Line in the Dirt", "Little Bird"... the list goes on and on.
- Especially "A Line in the Dirt," a song from the point of view of a man watching his marriage decay, realizing he and his wife don't love each other anymore.
- "Elizabeth On The Bathroom Floor", a song taken from his sister's diary, from an entry about a failed suicide.
"And I could try, but waking up is harder when you want to die.""'Cause I think that I am going to a place where I am always high.""My name's Elizabeth. My life is shit and piss."
- "Your Lucky Day In Hell" from Beautiful Freak, particularly the line:
And no-one will know my name until it's on a stone.
Tear Jerker / Eels
This alternative rock band has so many incredibly sad songs. Songs ranging from his sister, his mom, his father, himself, lost love, death, sickness and a whole lot of things. Some are even sung along really catchy and poppy tunes, however there are a lot of songs that are slow and depressive.