Living La Vida Loca and Macerena are both pretty dark.
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Komm Süsser Tod from The End Of Evangelion.
I didn't see wake up boo by the boo radleys in here.
It's about suicide
Mmmmbop
Looks like we all forgot Bruce Springsteen’s Born in the USA.
Adding You Haven’t Done Nothin’ - Stevie Wonder’s bitch slap to Nixon, and CCR’s Fortunate Son.
I mentioned Bruce & CCR in another nested comment a little before you posted, but I don't think I'm familiar with this Stevie song. I'll go check it out.
I'm Only Me When I'm With You by Taylor Swift. Granted, I have no experience with healthy relationships, but the relationship in that song sounds extremely unhealthy and codependent
Paul Thorn - Bull Mountain Bridge
Jonathan Coulton - Shop-Vac®
Charlie's Inferno is about an innocent man being tortured in Hell. It's a 50's style tune reminiscent of Mr Sandman.
Rise Against - Tragedy + Time
Porcupine Tree - Blackest Eyes
Mew - She came Home for Christmas
Straw Hat and Old Dirty Hank by Barenaked Ladies is about the real stalking of a Canadian celebrity by a mentally unstable man who thought she was in love with him.
on melancholy hill - gorillaz
Renai circulation, from the monogatari series. It's super cute but hidden inside is a cry for help.
You’re Gorgeous
I always find it funny how upbeat the Cambodia version by Pulsedriver is. PTSD and dropping bombs on cambodia. What a topic for a dance tune.
Checked out Apoptygma Beezerk's cover?
most of the after laughter album by paramore
also hey ya by outkast is often played at weddings while being about a relationship failing
A lot of Elliott Smith songs.
https://www.youtube.com/watch?v=Kkrb4h4weW4
I can probably put some more but this one has been on me for a while.
On the documentary 'shifty' they claimed that 'the land of make believe' by bucks fizz was written about Margaret Thatcher/Thatcherism. Really puts a depressing spin on it.
Lots of great choices here - I'll throw in Moon Over Marin by Dead Kennedys.
Sounds like a bop, but is actually about the destruction of the environment.
Someone else mentioned this too, but if anyone is into Japanese songs: I think there are probably more songs (especially Vocaloid ones) with extremely messed-up (and convoluted) lyrics than those that do not... I don't think most of them are well-known outside anime/vocaloid circles though. Trying to think about the more "cute and depressing" ones I could find:
NSFL
- Iyowa - Kyu-Kurarin: song is extremely cute. Supposedly implies breakup and suicide
- MikitoP - Shoujo Rei: involves two girls and one of them killed herself
- Mili - Nine Point Eight: one of my all time favorited; the title is somewhat self-explanatory
These are just what I could think of for now... A lot of songs with mentions of depression, suicide, etc... Other forms of messup, Telecaster B Boy is about being trans & not fitting in society I believe (song is a banger)
And this one is not "depressing" as-is, but Senbonzakura (that super famous Japan-esque song sung by Hatsune Miku that everyone has heard of) is about Imperial/WWII Japan sooo... take that as you will
Boys of Summer is about toxic obsession.
Little Foot Big Foot - Childish Gambino