I Like to Make Lists
Eight songs that crack me open.
I’m so good at tamping down my feelings that sometimes the only way to let go a little, to let myself feel my feelings, is to deploy one of The Songs. These are songs that I know will crack me open and possibly/maybe/definitely make me ugly-cry in my car. It’s not a particularly exciting list full of obscure bands or recent discoveries but a few of these songs are ones that recently reappeared in my life via Apple Music who’s apparently never not trying to get a reaction out of me. Here’s the current list:
“Graceland” by Paul Simon. This song got served to me in a playlist a few months ago and reminded me how much I’d liked it back in the 80s. I started listening to the whole album1 during the long drives back and forth from Richmond and now that I’m in my 50s, it hits totally different and the title track is just living rent free in my brain. These lines in particular:
She said, "Losing love
Is like a window in your heart
Everybody sees you're blown apart
Everybody sees the wind blow"
Oof. It just kills me because that’s exactly what heartbreak and grief feels like to me, like everyone can see right into me.
“Youth” by Daughter
I discovered this song years ago and it’s really haunting and sad. It really nails depression and the raw disillusionment that can come with it. But also, is just a beautiful song? It’s a good one to listen to if you want to FEEL SOME SHIT.
“Matilda” by Harry Styles
This one is my favorite song from Harry’s House. a surprisingly insightful and empathetic song about childhood trauma and emotional neglect. It’s beautiful and it makes me cry, so there you go.
“Birdhouse In Your Soul” by They Might Be Giants. I feel like this is a song that gets to a lot of people (at least, those who appreciate nerdy 80s music) but lately it’s been stabbing me right in the heart. It’s literally a song from the perspective of a blue canary shaped nightlight but it’s got a wistful loneliness to it and an important message - protect yourself and protect those that protect you. Also, I have to be careful with how often I let myself listen to this one because it likes to get firmly stuck in my head and then run on repeat when I’m trying to fall asleep.
“Oregon Hill” by Cowboy Junkies
I think I wrote about this one a few years ago. This is a beautiful song about a very cool and slightly disreputable neighborhood in my hometown, circa the 80s. It makes me homesick and therefore makes me cry without fail.
“Everyone Says ‘Hi’” by David Bowie
You won’t know this one if you stopped listening to Bowie in the 80s but Heathen, which came out in 2002, is an excellent album and you should give it a listen. It’s so good and “Everyone Says ‘Hi’” is probably my favorite track. He wrote it as a way to process his father’s death, though it had been decades:
“I had the sense of when my father died, and it seemed he had only gone away for a while and it was some time for me to reconcile that he wasn’t coming back.”
“Feel of the World” by Tift Merritt
This one is a sweet, nostalgic song about memories and the journey through life. If you don’t know Tift Merritt, start with Tambourine and then move on to See You on the Moon. See her live if you ever get the chance, she’s so underrated!
“Little Talks” by Of Monsters and Men
Such an upbeat, tragic journey of a song! The more you listen, the sadder it gets. And yet, still such a bop. I just never get tired of it.
‘Cause though the truth may vary, this
Ship will carry our bodies safe to shore
There was a fair amount of controversy about this album at the time but y’all, it’s beautiful and joyful and wistful. It has really stood the test of time. Give it a listen if you haven’t in a while (or ever.)



Great list! I recommend Noah Kahan for some good sad songs.
The summer that Graceland came out my family went to so many neighborhood barbecues where that was just playing in the background. I asked my mom "why don't we have a copy of that?" and she said "because if we want to hear it we can just go to a barbecue!"