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The all around prick
I love listening to video game soundtracks, not because I like the songs themselves, but because I recall the events surrounding the music and the impact it had on me as a player at the time. That's why a lot of what I listen to is pretty simple and not melodic-intensive.

Four songs that really stuck with me since I first heard them:

Just in case I haven't somehow made it clear enough, ICO is my favorite game of all time, hands down. When grabbing these links, I've come to the realization that these two songs are a huge factor in my opinion. They play at the perfect moments in the game to really drive home the emotional impact of the scenes, and cemented my conviction that no only is sound design crucial in a game, but how the most powerful pieces need to be unlike anything the rest of the game's soundtrack has to offer.

Even now, fifteen playthroughs later, these two tracks still get me. And I know they always will.

For me, the final fight with Pyramid Head in Silent Hill 2 was the most powerful moment in a game chock full of powerful moments. The raw emotion of James Sunderland finally accepting and conquering his inner demons shines through in this track, and stands out as a stark contrast to the creepy, panic-y, and depressing tone of the rest of the music.

Not saying this track isn't creepy in and of itself though. Far from it. That metal scraping really completes the piece. I've heard the music without it, and it feels much more empty.

I'll end off with a track in a game I've recently finished: Majora's Mask:

Holy. Mother. Of. God. Did someone break Nintendo's favorite toy when this game started development? Majora's Mask was such a stark contrast to every other game in the series I've played (even the more gloomy Twilight Princess) and that's almost entirely because of the Moon.

Having a hero fail to save the world in time over and over and over again is already depressing enough, but hearing this in the final hours of each three day cycle, knowing that there's nothing you can do to stop it except go back in time and undo all the good deeds you've accomplished thus far, really drives home the bleakness of the end of the world. Wandering around Clock Town and seeing its residents either succumb to panic or face their impending deaths head on brings out a surprising amount of depth to the NPCs that not many games can replicate.

I'll stop now before I bore you all with my ramblings. What about you? What are your favorite music tracks from games? You certainly don't have to explain yourself in as much detail as I did, and maybe you just like listening to the tracks rather than remember what was happening at the time? That's fine too.
Songs means there has to be singing right. So here are some personal favourites.

Anything from most Castlevania games, really :D
Usually random picks when I draw or work.
Stand back. Artist at work. I paint with enthusiasm if not with talent.
doesn't live here anymore
Meta choice:

BBQed to death:

I don't know if I can post my FAVORITE track, but, in fairly recent memory, here's a battle track from Mystic Ark (which is a flawed snes gem if you haven't played it) that pulled me up by the shirt collar and said, "I know you're trying to play the game, but how about you stop and listen to me, you FUCK."

The change around :22 is what got me.

Legend of Mana has a great soundtrack; this one sticks in my head a lot:

Also, I love me some Paladin's Quest/Lennus 2 for how unique they sound:

My unquestionable devotion to the glockenspiel (and melodic percussive stuff in general) is due in large part to that franchise.
"Eyes on Me" because it's one the first actual songs I ever heard in a videogame.

Also, "Luna's Boat Song"

And the intro from Suikoden 3 is just awesome. I love this kind of 'worldly' music.
The TM is for Totally Magical.
After ages of thinking. I had to boil it down to these.

There are plenty more, but we'd be here all day.
You expect me to /choose/ ?

Same here. Though my personal pick ATM would be the MIDI Power X68000 collection.
never been able to put this into words.
i picture someone floating in space, alone.
helplessly watching the world end.
tears float inside there helmet.

this one's battle music.

this ones. cornerias theme.

Moon Music is still the best
I wanna marry ALL the boys!! And Donna is a meanc

I have a thing for final boss music--
The 524 is for 524 Stone Crabs
Not really in-game, but the accompanying vocal tracks of Earthbound Zero (Mother 1) move me.

... ESPECIALLY this one:
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