In my opinion, most Mountain Goats songs. John Darnielle is an amazing songwriter, and he tackles very difficult subjects, especially in his earlier stuff. The Sunset Tree album is all about growing up with an abusive step-father, Tallahassee about a couple who fall apart, Full Force Galesburg about a small town you can disappear in, etc. Some of my favorites include “The Mess Inside” about two people that can’t find the love they lost, “No Children” about a couple that hate each other, and “Jeff Davis County Blues” about a sort of meditative experience after a breakup. I’d give it all a listen. To go even deeper, the albums All Hail West Texas and In League With Dragons have sort of companion podcast seasons (I Only Listen To The Mountain Goats) where Darnielle and Joseph Fink of Welcome to Nightvale go through each song, the inspiration, the meaning, stuff like that.

Billy Joel songs tend to have that character.

The entire Nurture album by Porter Robinson. Deals with loss, existence, joy, AI, etc.

The Wreck of the Edmund Fitzgerald

Don’t go boating in a storm, folks.

Walk like a warrior - Dead Prez

Nonviolent protest will never win what needs to be won

Paramore - This is why

If you have an opinion
Maybe you should shove it
Or maybe you could scream it
Might be best to keep it

To yourself (to yourself)

As I hurtle towards middle age, I find Time by Pink Floyd more and more relevant

Ticking away the moments that make up a dull day
Fritter and waste the hours in an off-hand way
Kicking around on a piece of ground in your home town
Waiting for someone or something to show you the way

Tired of lying in the sunshine staying home to watch the rain
You are young and life is long and there is time to kill today
And then one day you find ten years have got behind you
No one told you when to run, you missed the starting gun

And you run and you run to catch up with the sun but it's sinking
Racing around to come up behind you again
The sun is the same in a relative way, but you're older
Shorter of breath and one day closer to death

Every year is getting shorter, never seem to find the time
Plans that either come to naught or half a page of scribbled lines
Hanging on in quiet desperation is the English way
The time is gone, the song is over, thought I'd something more to say

Home, home again
I like to be here when I can
And when I come home cold and tired
It's good to warm my bones beside the fire
Far away, across the field
The tolling of the iron bell
Calls the faithful to their knees
To hear the softly spoken magic spell 

Avatar - Going Hunting - world vs self

Ozzy Osbourne - See You On The Other Side - loss of others

Iron Maiden - No More Lies - the inevitable end

Also maybe some Alice in Chains songs from the Layne Staley era, but for me those depend heavily on the mood I’m in.

Wrong Ones by Julliette Reilly

I find one line particularly powerful, and it’s been used in a couple famous songs.

Jenny Lou Carson (1944), made popular by Willie Nelson (1966)

I’d trade all of my tomorrows for just one yesterday For what good is life without the one you love I’d trade all of my tomorrows, they’re worthless anyway If my arms can’t hold the one I am dreaming of

Just an empty world is all I have before me I’d give anything if you were with me now I’d trade all of my tomorrows for just one yesterday I don’t want to live without you anyhow

Kris Kristofferson Me and Bobby McGee (1969)

And I’d trade all of my tomorrows For one single yesterday Holdin’ Bobby’s body next to mine Freedom’s just another word for nothin’ left to lose Nothin’ left is all that Bobby left me.

I like The Christians And The Pagans by Dar Williams. It’s a simple song about a multi faith extended family being able to just enjoy and celebrate Solstice/Christmas with understanding and openness and without drama. Like, we really all could get along if everyone chilled.

As I grow old and struggle with the break up of a marriage of ~19 years: Both Sides Now, from Joni Mitchell

It’s a bit long to paste here, so just Google it if you care.