I'm a big fan of sad music!
From games, in no particular order...
The only song with vocals in To the Moon.
The strangely eerie main theme from Cubivore.
The diary music from Yume Niki.
The refugee camp from Xenoblade.
Lonely Rolling Star from Katamari Damacy.
Roaslina's story book theme from Super Mario Galaxy.
The memory music from Super Mario Mario.
If we include anime...
The Memory of my First Love from The World God Only Knows.
I'm Losing You from Space Dandy.
Abyss of Despair from Persona Trinity Soul.
Anohana ending.
Ichiban no Takaramono from Angel Beats.
And extending that to regular songs...
Stories by Trapt.
Heart Rate by Shounen T.
Bullet by Hollywood Undead.
What Sarah Said by Death Cab for Cutie.
Especially the lyrics to Skies by Protest the Hero.
5 Year Time by Noah and the Whale.
From games, in no particular order...
The only song with vocals in To the Moon.
The strangely eerie main theme from Cubivore.
The diary music from Yume Niki.
The refugee camp from Xenoblade.
Lonely Rolling Star from Katamari Damacy.
Roaslina's story book theme from Super Mario Galaxy.
The memory music from Super Mario Mario.
If we include anime...
The Memory of my First Love from The World God Only Knows.
I'm Losing You from Space Dandy.
Abyss of Despair from Persona Trinity Soul.
Anohana ending.
Ichiban no Takaramono from Angel Beats.
And extending that to regular songs...
Stories by Trapt.
Heart Rate by Shounen T.
Bullet by Hollywood Undead.
What Sarah Said by Death Cab for Cutie.
Especially the lyrics to Skies by Protest the Hero.
5 Year Time by Noah and the Whale.