Fast Car
Pumped Up Kicks
Flowers on the Wall
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Fast Car
Pumped Up Kicks
Flowers on the Wall
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
Charlie's Inferno is about an innocent man being tortured in Hell. It's a 50's style tune reminiscent of Mr Sandman.
That's like Paul Simon's entire schtick. Alongside downbeat songs with uplifting lyrics.
Little Foot Big Foot - Childish Gambino
Hey Jealousy by The Gin Blossoms comes to mind.
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.
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
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
The entirety of hissing fauna are you the destroyer by of Montreal
Ruru's suicide stream ? Would that one count ? Damn it's like all the songs flew out of my brain the moment I read this question ahahahh
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
Boys of Summer is about toxic obsession.
Just Ain't Gonna Work Out - Mayer Hawthorne

https://www.youtube.com/watch?v=Kkrb4h4weW4
I can probably put some more but this one has been on me for a while.
You’re Gorgeous
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
Mmmmbop
Club America by The Cure