Here's my top six songs (least sad to most sad) on the subject. Why top six? Because I feel like it this time around.
#6.
Ezlo's Past
And then there's
Ezlo's Past from Minish Cap. This was a very sad song when I first heard it, and it completely encompasses the feeling of Ezlo's sadness at Vaati's betrayal of him. It just really strikes me as very sad.
#5.
Song of Healing
The
Song of Healing was sad to be sure. After all, it was used when people died or were dying most of the time (the one and only exception being when you get the Gibdo Mask, but it was still sad that a little girl had to be so brave and stuff, that really gets to me the most out of all the major times you use the Song of Healing). However, the way it sounds towards the end makes it sound very optimistic, almost as though it's like "[character's name you healed here], don't worry, Link will carry on your tasks and finish what you were not able to" which actually is exactly what happens in all of the times you use it, save for when you get the Gibdo Mask.
#4.
Serenade of Water (Rutela Remix)
Then there's the
Serenade of Water (Rutela remix). That's definately one of the top contenders in my book and with good reason. The song is like the living embodiment of sadness, completely encompassing the sadness that Prince Ralis must go through when he regains his health as well as the sadness of Queen Rutela not being able to be with her one and only son any more. That just gets to me so much.
#3.
Aryll's Kidnapping
Aryll's Kidnapping is also incredibly sad. Not for the first 40 seconds, but by the time 0:42 kicks in, the sad part begins and it's like you really feel Link's pain of having his sister kidnapped by a giant bird, never to be seen again.
#2.
Grandma
Another top contender is
Grandma from WW. I don't know whether or not it's my nostalgia speaking, but this is just so sad. To see Aryll, so sweet and innocent, being spirited away by the Helmarock King and then his kind old Grandma break down in sadness until it drives her to be physically ill.
#1.
Ballad of the Wind Fish
There were quite a few contenders for the top spot on my list, ranging from
Princess Zelda's Theme from WW (I swear, Zelda's Lullaby has to be the most remixed song in the series, heck ST had a full three remixes of the darned song) to
Aryll's Theme from WW, but the second I heard
The Ballad of the Wind Fish again, I knew I had found my number one saddest Zelda song.
It just captures that feeling of never being able to come back to Koholint Island, or even being able to see the people you grew fond of (Marin and Tarin for one). It's all around a very sad song.