I'm curious to know what songs mean the most to you.
For me, it would be the song My Immortal. It's one of the many songs that remind me of my ex-best friend/sister. She wasn't my real sister, but she was like one. I loved her to death because she always accepted me. Then one day she stopped talking to me, and wanted nothing to do with me. I tried to get her back so many times, but she refuses to talk to me. This song is one of the ones that holds a special place in my heart because of her. Because I've tried so hard to tell myself that she's gone, yet she's still with me all this time. It's really hard to explain. :/
Another song that means a lot to me is Try by Simple Plan. This song saved my life. I was literally ready to die when someone mentioned it on Tumblr. I literally started bawling when I heard it.
I have a lot of songs that mean a lot to me, but those are two that I can think of right off the bat.