Headlights by Eminem and Nate Ruess. It isn't a very sad song. But it carries the vibe

Let it Go by James Bay.

Jar of Hearts by Christiana Perri is also a nice one.

Big Girls Cry by Sia

Also For the damaged coda by Blonde Redhead.

Blue Eyes by The Who

https://youtu.be/Y6-QvBz9_lY (lying to you)
Or anything by Keaton Henson tbh

The cats in the cradle

The Real Me, and Away in the Sly by MandoPony
Who lives who dies, from Hamilton
Words Fail, from Dear Evan Hansen

It's quiet uptown from Hamilton

Sunshine by monkey majic

Away in the sky by MandoPony. Sorry. Misspelled.

Death of a Bachelor -Panic! at the Disco
It's more bittersweet but still amazing

Most songs by Paloma Faith (my favourites are Only love can hurt like this, New York, and Picking up the pieces)
Dive, or Happier by Ed Sheeran
Not the only one by Sam Smith
Born to die by Lana Del Ray
Amnesia by 5sos

Sad by Maroon 5
December by Neck Deep
When I'm Gone by Eminem

https://www.youtube.com/watch?v=h2pe01hEwUg

Make me cry everytime

Creep by Radiohead

Mockingbird by Eminem too @cakelover. If When I am gone is considered.

fuck love by xxxtentacion.... basically his whole album

You ruin me by The Veronicas
Stone Cold by Demi Lovato
The heart wants what it wants and Same old love by Selena Gomez
Dangerously and Attention by Charlie Puth