I love sad songs.
When I’m sad and I want help to feel the maximum amount of sadness I possibly can. When I’m lonely and I want to know that some other human in the world feels deep things too. When I’m hopeless and I need to hear something that’s so beautiful I can tell what emotion it’s portraying even without any words. When I’m perfectly happy but I just kind of randomly want some synthetic sadness.
Listening to sad songs is the most communal experience I partake in by myself. Tragedy is unrelentingly universal, and sometimes that’s just downright beautiful.
What makes a song sad is wildly subjective, but here are my personal top 10 most favorite, most sad songs.
1. Pulaski at Night – Andrew Bird
This song just sounds beautiful. But something about it also sounds like unfulfilled longing. (Whatever that means.)
2. We’re All In This Together – Old Crow Medicine Show
This song sounds like tiredness. Like a bunch of people admitting their tiredness all together. I think the “This” in the title is referring to being tired. Just some mass exhaustion. But it also sounds oddly hopeful, and that only adds to my desire to cry during the song.
3. Dissolve Me – alt-J
Here’s what I have to say about the band alt-J: if there’s one thing they do well, it’s incoherent mumbling that makes my soul feel a very particular emotion that I’m never able to put into words. The emotion of this one revolves around sadness, with flavors that I don’t quite understand. To try to make more sense out of what this song does to me, I’ve looked up the lyrics… which hasn’t helped. I’m still not sure if the sentiment of the song is sad or happy, but it sure feels sad to me.
4. Agnes – Glass Animals
I’ve had friends argue fiercely with me that this song is not sad. The first time I heard it, I didn't think it was either. But I added it to my playlist, and the more I listened to it, the sadder it seemed. Glass Animals' signature use of weirdly addictive-sounding assonance sounds particularly droopy in this song. And careful listening to the lyrics confirms that the song is sad – it's all about some some sort of loss of a relationship.
5. Boats & Birds – Gregory and the Hawk
This song just sounds small and sad to me. It sounds like the singer is miserable but out of love is pretending to be happy. That’s an extremely sad concept to me. (Also, for what it’s worth, here is a cover that I almost like better than the original… I think I like it more because it sounds even lonelier and sadder.)
6. Cathedrals – Jump Little Children
An aching little ditty about feeling existentially out of place and seeking “home,” with nostalgia sprinkled over it. If that’s not enough to make your heart ache and your eyes swell, then I think I might envy you.
7. Rachel’s Lullaby – dandelion hands
This is an instrumental lullaby. I haven’t been able to find a song that makes me feel so much like crying without even any words. Most lullabies are supposed to gently and peacefully lull you to sleep, but this one seems to say: “I know. I’m exhausted, too. Try to rest now.”
8. My Friends Don’t Know (I Know They Hate Me) – dandelion hands
It’s almost cheating putting the same artist twice on this list, but I figured it was fair to include one with words, too. I don’t really know what the words are saying because they are so faint and sad, but based off the depressing words in the title, I don’t think I want to analyze the lyrics too much.
9. Another New World – Josh Ritter
Most of this list is me interpreting the sounds of certain songs a certain way, but I can confidently say that this one is an intentionally heart-wrenching one. With no chorus, Josh Ritter sings a story, beginning to tragic end, about a man greedy for adventure and his beloved ship. It’s a beautiful, sad story with an even sadder deeper meaning if you look for it hard enough.
10. The Curse – Josh Ritter
Again, this might be cheating, but I think Josh Ritter deserves to be on here twice. This is the only song that has forced me into stinging tears without any of my own sadness to help. Josh Ritter is really good at singing deeply sad, beautiful stories. There was one day when I listened to this song on my way to work, and I really, truly listened to the lyrics for the first time. Luckily my commute was long enough to give my tears time to dry. The lyrics continue to sink deeper and the underlying meaning richer each and every time I hear this song. This should certainly be a go-to for any time you want to intentionally listen to music just to feel deeply.