The most depressing song u like?

For me, theres something so gut wrenching about "Don't Fear The Reaper" by the Blue Oyster Cult. I also get this same feeling listening to "New Mistake" by Jellyfish. Both of these songs are not necessarily "sad" songs per se, but they give me a feeling I can't put into words. 

I wanna know ur depressing bops, I like listening to these when I write xP

"Swamp thing" by the Chameleons, as well as "The Painted Bird" by billy vincente. they both have their own unique haunting sounds, but man, besides swamp thing being one of my favorite songs of all time, it's such a desperate piece. and painted bird's lyrics are simple, but effective when you just feel, stuck. 

edit: also "Half Life" by trocadero. it's a fun one, a belter if you're in the right mood, but yeah, the singer/subject is not. having a good time smjdfkjsgsajd. 

 i'll change for you by mitski 

Anything by dead butterflies really

the light behind ur eyes by mcr 

Sorry kids, but your music sucks today. The only thing depressing about it is having to listen to it. 😂

Shouldn't we begin with the obvious?

let down and things to do and like idk dtmf and pumped up kicks

Each passing verse gets darker and darker. When you're thinking 'wow, this is messed up. It can't get worse than this', and then the next verse is worse! 

anything by mitski to be honest, her songs are incredibly gut-wrenching

This may sound a little odd but “not my responsibility” makes me disassociate SO HARD. Like I like the song but I can’t listen to it otherwise everything will seem not real and I will feel like I’m just watching everything without feeling like I’m actually there

This is kind of silly but one of my favorite depressing songs is actually a salsa song of the  70. It's called El día de mi suerte (The day of my luck). It talks about a persons who's became orphan and beging to wait for his luck to change.

well fuck me, i accidentally closed the page and i have to write this again

'synafolden' by apati, 'dark winter depression' by drowning the light, 'eufori' by apati, 'the longing' drowning the light, 'ord fran graven' by apati, 'the hope' by blade and bath, 'frozen in melancholy' by wintercult, 'how much for the hope' and 'eyes of a homeless dog' by psychonaut 4, 'sorrow' by kekht arakh* and ofc all things by none and intig

i wouldn't say this go by the conventional sound of sadness but i hold them very near and dear to my heart and i love the chemicals they cook in my brain. even though they could ruin my day i find myself coming back to them like a druggie

*i hate what kekht arakh has become and to be honest, apart from 'sorrow',
'through the branches to eternity' and his earliest stuff i don't think
he has much good music. and god especially now.
if i could i'd spit on him

forgot about this one but it's another candidate

I think Teen Love by No Trend is pretty sad. It's about these two teens who find interest in each other and build their relationship based off of societal standards and cliches, as if there were no true connection/emotions, they then both die a tragic death via car accident. The instrumentals make it sound really upbeat, and it's just really pleasant to listen to 

just about anything by adrianne lenker (hah) gets to me, but this cover of her song "anything" always makes my chest heavy. songs by her just reverberate through me like a bell. i've also been listening to the "Nothing's about to happen to me" album by mitski a lot lately.

Smiley Wonderful is underrated.

Jordan River by Nastyona is my all time favorite 

for sure black star by radiohead. it speaks to me a lot as a mentally ill person who's been through several relationships and all of which have failed in some form. my longest relationship was about 2 years, and during one of the worst moments in my life, i decided to break up with my partner at the time, but we still remain good friends.

and i listen to the lyrics of this song and search up the meaning and the moment it clicks, i begin sobbing like crazy.

"troubled words of a troubled mind
i try to understand what is eating you"

and i so desperately want people to get that i'm struggling. i'm so sick of hiding what i really feel deep down. but at the same time i don't want to be a burden, a heavy load. and especially not for someone who i adore, because what if after everything i tell them, they don't want to be with me anymore? what if i say too much and weird them out? they're probably not ready for such a huge commitment yet. to carry this burden with me. but god, i'm so sick and tired of being alone and carrying everything on my own.

a helping hand wouldn't hurt. moral support wouldn't hurt.

sorry for the long ass comment but this song truly means a lot to me in so many ways. i'm grateful for music and its existence. without it i don't think anyone would be here today.

This is a good question so I wrote out a list and tried to narrow it down. One isn't happening so, forgive me, here's a few songs that specifically bum me out (in a good way...?):

Reservations by Wilco
Two Daughters and a Beautiful Wife by Drive-By Truckers
Pretty Good Year by Jay Bennett (originally by Tori Amos)
Narcolepsy by Ben Folds Five
Good Times by Jim O'Rourke

There's fifty or so more where those came from, but for now that's my one(s).
Also as an aside, cool to see Jellyfish mentioned in the op, they don't get near enough love.