The process of listening to depressing songs can either be horribly triggering or wonderfully cathartic, and for me it is often both. I absolutely adore sitting down with a pair of headphones to indulge my innermost melancholic machinations. Depending on how you personally respond to sad songs, this list will either be a collection of the most beautifully evocative tunes that you should absolutely check out if you haven’t, or a cautionary curation of tracks to avoid like the plague. Should we even say “avoid like the plague” anymore?
Kicking off this list with a Phoebe Bridgers song almost feels like cheating. Her rise to prominence as the millennial queen of depressing songs and self-aware tweets is inescapable. While I could have picked just about any one of her songs, I had to go with “Funeral” because of the juxtaposition of its narrative setup with its incredibly on-the-nose chorus.
The lines “Jesus Christ I’m so blue all the time, and that’s just how I feel, always have and I always will” are so melodramatic, but they work so well only because they are preceded by the harrowing idea that she’s going to perform at a funeral tomorrow of a kid who’s only a year older than her. Her vulnerable voice combined with the sparse indie-folk instrumentation is just so immediate that even the Boston Dynamics dancing robot would have to lie down.
My inclusion of this song is actually almost completely removed from the lyrics themselves. They’re minimalistic and straight forward in their depiction of desperation as a relationship draws to a close. What really sells this depressing dirge is the signature vocal delivery of Robert Smith and the haunting beauty of the instrumental. Just zone out, nod your head, and pretend for five minutes that everything is definitely not going to be alright.
Alright, strap in for this one. This nine-minute piece comes from the album “Hand Cannot Erase,” a concept album inspired by the true story of a British woman named Joyce Carol Vincent who died in her apartment and not a single person noticed for almost three years. With inspiration as somber as that, there were bound to be some depressing songs on the track list.
However, “Routine” simply exists in a higher plane of emotion than its counterparts. The guest vocals from Ninet Tayeb are transcendently powerful and the music video depicts the story of a wife and mother who lost her husband and two sons in a school shooting, yet she continues her daily routine as if they are still alive, even cooking meals for them. It will harvest your tears.
I could populate an entire list of the most depressing songs from the golden age of emo pop-punk, which I like to refer to as “sad boi classics.” Instead I’ll just provide the most immediate track of them all. It’s a two-minute piano ballad that sounds exactly how the title suggests it would. It may be aggressively corny, but cancer is the inevitable reminder that life is never fair. It touches everyone’s life sooner or later, and I defy anyone to listen to this song and not feel either reverent or broken-hearted about a loved one who lost their battle.
Easily the most mysterious entry on this list, Sleep Token is an anonymous band that is said to worship the deity understood by humans to be simply called “Sleep.” While their gimmick may sound off-putting and impersonal, their sound is vulnerable and heartfelt. This track is especially moving because of the tortured conviction of the vocals, and it even wraps up with the sound of the singer actually crying. I’m right there with you, my guy.
Sometimes context can elevate an ordinarily woeful tune into one of the most depressing songs imaginable, and this is a great example. Without explanation, this song is still moving in its own right; its somber, almost country-like timbre laments the inability to communicate with a lost loved one. However, the abject sadness gets turned up to eleven with the knowledge that the song is about the band’s fallen drummer, Jimmy “The Rev” Sullivan. The track was released less than a full year after his tragic death at just 28-years old.
Remember what I just said about context? It applies here but in a much different way. While the previous song was about a fallen friend, “Lazarus” was Bowie’s goodbye to the world. He knew he was dying when this song was written, and in fact he did pass merely a few days after the release of the “Blackstar” album. The music video takes place in a hospital room and is somehow both tragic and uplifting at the same time. It was a legend turning his own death into a remarkable work of art.
If my picks for this list didn’t already make it obvious, I’m not the biggest fan of modern pop music. It’s just generally not for me, but even a curmudgeon like myself can’t deny the haunting beauty of this duet, and omitting Billie Eilish from a list of depressing songs would just be willfully ignorant. She’s the voice of a new generation growing up with a much different understanding of mental health.
Jumping back in time about 45 years, these lyrics leave far more room for interpretation than most traditionally depressing songs, and that’s what’s so great about it. Whether you think it is about original Pink Floyd member Syd Barret, a breakup, growing apart from old friends or anything else, you’re right. The imagery of the lyrics “We’re just two lost souls swimming in a fish bowl year after year” is just so undeniably evocative, and I’m still not even really sure what it means! Just let this transcendent song fill your ears, and let your mind wander.
I had to do it. We’re finishing off this list with a song that is not a recommendation at all, and in fact I implore you all that no one ever listens to this song again. Ever.
If somehow by now you’ve still never seen the ASPCA commercials that combine McLachlan’s somber tunes with images of abused animals in order to extract your guilt for donations, then you should consider yourself extremely lucky. I’m not even going to link this song. Seriously, don’t listen to it. I’m listening to it right now, and those poor animals are burned on my retinas. There’s no turning back for me, but there’s still hope for you!
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