Any songs that you think are really sad? What point do you think it's the saddest?
My entry: https://youtu.be/lRhQPomD-I4
Saddest bit:
Chara: "If I could only hit you once it would be over,"
Frisk: "But the consequences last forever!"

This one is quite sad

Hawkind - Infinity

https://www.youtube.com/watch?v=Kj2Ttis3D3c

Sad lyrics

'I used to be of human kind, I had a life to lead.
But now I'm frozen in a dream, my life is lost it seems..."

And later on

"I met her in a forest glade, where star-beams grew like trees,
I did not take her for a witch, she wasn't what she seemed...
She turned the key of endlessness and locked me in a dream."

And this one

2000 light years from home

https://www.youtube.com/watch?v=wcy8o0gj-A0

"It's so very lonely, you're 2000 light-years from home"

Pretty sure this isn't that sad, but it's amazing: https://www.youtube.com/watch?v=B7xai5u_tnk

This one is sad but here we go! It is not a song so..

https://www.youtube.com/watch?v=3ueDnx5ONII

I have a few:
Shadow of the Day by Linkin Park: https://m.youtube.com/watch?v=8H7ZwDawsb4
"In cards and flowers on your window
Your friends all plead for you to stay
Sometimes beginnings aren't so simple
Sometimes goodbye's the only way, oh"

World So Cold by Three Days Grace: https://m.youtube.com/watch?v=0DQimvlEpjY
"Living in a world so cold
Wasting away
Living in a shell with no soul
Since you've gone away
Living in a world so cold
Counting the days
Since you've gone away
You've gone away
From me"

Iridescent by Linkin Park: https://m.youtube.com/watch?v=gUmtn-BMB6o
"Do you feel cold and lost in desperation
You build up hope but failure's all you've known
Remember all the sadness and frustration
And let it go, let it go."