what is the most heartbreaking song in your opinion?

These probably aren't in your generation of listening but : 1. Crazy - Patsy Cline 2. Crying - Roy Orbison and KD Lang 3. I Want to Know What Love Is - Wynonna

To a Friend (Adventure club remix) by alexisonfire

Who I am by smile empty soul

insomniatic meat by finch

Blue by a perfect circle

Locked In by Scary kids scaring kids

there a shet ton more but i can't think of them at the moment.

Hurt- christina A

subjectively speaking, "Father of Mine" by Everclear or Johnny Cash's version of "Hurt". Also, "Make Believe" by The Burned.

without a doubt. Bright Eyes- it's cool we can still be friends(listen to it you will understand)

and another white lies - change ( dawn golden remix)

Those song that talks about banging different women :P.

Evanescence - my immortal

It's different and unique.