I always thought Free Four by Pink Floyd fit that category well.
this post was submitted on 03 Sep 2025
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Ye, Renew the Plaintiff by Of Montreal
Hey Jealousy by The Gin Blossoms comes to mind.
Bullet by Hollywood undead.
Singing about killing himself in a super upbeat song, even has kids at the end going "I wish that I could fly, way up in the sky", the part where he was singing about jumping off a skyscraper.
The Motown hit Keep Me Hanging On by the Supremes is the classic example of this.
It was even recognized for its pathos and turned into a sadder slow version by psychedelic band Vanilla Fudge
This is probably a controversial opinion, but Ive always felt a little bad for the guy this song is about.
I think it's unfair for her to say he doesn't care a thing about her. He obviously does. If he didn't he wouldn't want her to still be a part of his life.
This song is just about two people who want different things out of their relationship, and the singer is just unable to accept it.
She has the ability to cut him out of her life if that's what she really wants, same as he does. She should cut herself free if it's too painful for her to be his friend.
I feel that. Maybe this song is her way of cutting herself free? Or by telling him to make a decision, she's giving him more autonomy than if she just left. Like she's saying, "Look, we need to commit to a decision, no more up and down, which way would you have it?"
Or by telling him to make a decision, she’s giving him more autonomy than if she just left. Like she’s saying, “Look, we need to commit to a decision, no more up and down, which way would you have it?”
I can see that, though it feels to me like from the context of the song they have already had that discussion at least once before.
I know that it hurts when you feel a certain way about someone and they don't feel that way about you- it can hurt a lot and it can take time to come to terms with it- and I don't' think removing yourself from their lives is an unreasonable solution if you are having trouble dealing with it- so I definitely feel empathy for the singers pov as well.
May I introduce you to The Smiths. Rusholme Ruffians and There is a Light That Never Goes Out are great examples, but really it describes most of their catalogue.
Rise Against - Tragedy + Time
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?
Charlie's Inferno is about an innocent man being tortured in Hell. It's a 50's style tune reminiscent of Mr Sandman.
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.
Brown Sugar
A lot of that album was pretty subversive but hidden behind upbeat rock. The olds didn't realize what the kids were listening to because they just heard pop rock.
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
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.
Little Foot Big Foot - Childish Gambino
You’re Gorgeous
Boys of Summer is about toxic obsession.
on melancholy hill - gorillaz
Renai circulation, from the monogatari series. It's super cute but hidden inside is a cry for help.
A lot of Elliott Smith songs.
Porcupine Tree - Blackest Eyes
Mew - She came Home for Christmas
Love - Forever Changes. The whole album.
https://youtube.com/playlist?list=OLAK5uy_lIfiGGgw0nJ6H3UcVvp1UbFhwr0LGPiBE
Like half of Fall Out Boy's discography. "Hum Hallelujah" gets a special mention for literally being about a suicide attempt. Also "Dance In the Dark" by Lady Gaga, "Stomach Vs Heart" and "Humor of the Situation" by Barenaked Ladies ("Angry People" as well), "Slip Slidin Away" by Paul Simon, "When I Come Around" by Green Day...suffice it to say, I enjoy this trope a lot :P