Don't mind me, I'm in a particularly nostalgic mood which tends to leave me prone to a deep sense of longing for days gone by. In turn (or inspired by) how about the songs that break your heart (good or bad) and why?

The 1up Show Ballad

"Goodbye, so long
I bet you'll miss me when I'm gone
Promise you won't stop
You'll keep it on
I'll see you all on the 1up show
That's how I'll always
My friends are going on
and I'll see you all
on the 1up show"

EGM was my favorite magazine back in the day (are any of you kids old enough to remember begging your moms for a video game magazine at the grocery store?). In 2006 I learned about their website, the 1up Network. From there I got into podcasts, the 1up show, and a whole community of like minded people I could feel a sense of kinship with in some way. It's through video game podcasts that I first learned about the brony community, and that triggered me to learn more about it and eventually to be where I am now.

The 1up Show was a series I looked forward to every week with baited breath. I was very sad to see it go, but was happy to see the site and the brilliant people there carried on. This year, 1up finally came to an end. And my memories turned to that watershed year of my life with all the good times and bad. It breaks my heart to know those days will never come again.

Highway Patrolman - Bruce Springsteen

You can always count on Springsteen to write a brilliant song. This song is about two brothers, one good, the other well, not bad, but certainly not good. This song is the tale of those two brothers, and just how far one will go to protect those he loves and what we're willing to look over for the sake of that love. It's a beautifully heartbreaking tale.

Into The West - Annie Lennox
[youtube=http://www.youtube.com/watch?feature=player_detailpage&v=-RDuQfSwKfY#t=28s]
I love Lord of the Rings, the books and the films. This song to me speaks of the tragedy of the story, and the great hopes built upon that tragedy. Its a wonderful song that I've turned to in some of my darker moments.

Farewell and into the Inevitable - Sam Hulik

I'll always have a soft spot for piano and strings. This one is mostly due to the context I heard it in. ME3 fans, you'll know what I'm talking about.

Everything's Alright - Laura Shigihara

I'm not crying... I... I just ate an onion...

On a slightly different note:

Anybody who has spent at least 15 minutes in my presence will tell you that I have a dangerous obsession deep seated love for the protomen, and a giant man crush on their phenomenal singer Raul Panther in particular.
The Will of One is one of two songs in their collection that raises the hairs on the back of my neck with the sheer emotional power behind the singing. All their albums (except the Queen Tribute album) tell a cohesive narrative about a uncaring world trapped under a tyrant. The entire song really works as an emotional build towards the moment towards the end where the protagonist stands at his brother's grave reading the graffiti across it. The moment Panther sings our "Hope rides alone" can still hit me right in the heart when i listen to the whole album straight through. And in light of that, It remains my top pick for any list of heartbreaking songs, despite being very different then the type of song that usually ends up on such lists.

903342>>903504

I listened to this just after reading The Letter. Most of the songs on the CD are sad. This one is about a young couple who have an abortion and start to regret it. A councilor tells them to treat it as the the child died and give it a name and visit the grave.

This is another great one. Don't really know why, but it put me into a three-day depression a while back. Actually, it was shortly after being introduced into the fandom.

903342>>903545

This one doesn't have a particular story behind it outside of being the theme to one of my favorite fictional characters.
The song in general, and especially this version, seems incredibly melancholy, and is one of my go-to song's when I'm feeling down. Needless to say, It's frequently featured on the soundtrack to my life.
Just makes me want to make a cup of black coffee and sip it while looking out at the rain, waxing nostalgic.

904647>>903342

This one isn't like heartbreaking sad, it's more of the "Oh fuck, that happened" sad. The song is the story.

And this one nearly broke me.

905606
Yeah, that second one is one of those songs that just punches you right in the gut.

905619
Then rapes you as you are doubled over and leaves you in the gutter without so much as a kiss.

905709
I mean geez, the least it could do is buy you dinner first.
Maybe bring you some flowers.
A box of chocolates.
Then rape you.

905721
A courtesy kiss would be enough. But NOOOOOOOO.

905940
Some people's children, I tell ya.
Absolutely no sense of manners.
In my day there were things you did when you were going to rape somebody. It was expected.
It was Common damn courtesy.