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[ULTROS!]

Personal favorites:

Silent Hill:
Room of Angel - Probably one of the best music in the Silent Hill series, not to mention one of the saddest.

Please Love... Once More - Very emotional, song played when

Spoiler

Heather's father, Harry Mason, was murdered

Final Fantasy:
Anxious Heart - Music is full of despair. Will definitely remind you of the Midgard slums.

Celes (piano version) - Piano version is awesome, will remind you of

Spoiler

Celes' Leap of Faith

.

 

[Pooya]

Never Forget from Halo 3.
MGS Peace Walker "Zero Allies!"
amazing track really!

 

[yencid]

dearly beloved

to zanarkand (this one is orchestrated tho)

 

[thcsquad]

Suikoden, Theme of Sadness.

Take your pick:
http://www.youtube.com/watch?v=h4ZxNJ7FOGo - Ensemble version
http://www.youtube.com/watch?v=58gHcb5oVUU - Guitar version

 

[SturokBGD]

Silent Hill:
Room of Angel - Probably one of the best music in the Silent Hill series, not to mention one of the saddest.

Saw the topic title, came to post this, saw it was the first thing written. Couldn't agree more.

 

[Whimsical Phil]

Romantic:

Gitaroo Man - The Legendary Theme

 

[Danne-Danger]

Like in every thread about good VG music, there's Outlaws:

http://www.youtube.com/watch?v=mzS600dZbPo

 

[yencid]

Romantic:

Gitaroo Man - The Legendary Theme

had this on psp... such a fun game!

 

[Sacha]

Nier - Grandma

 

[BorkBork]

Mother 3 - Gentle Rain

Mother 3 - Flowers

The game is full of em. More nostalgic/sad/melancholy than romantic of course.

 

[GCX]

Farewell Hyrule King

 

[subversus]

http://www.youtube.com/watch?v=OuhhithTvMI

Witcher - Dusk of a Northern Kingdom

 

[squall211]

Grandia: The Sandy Beach of Ganbo


http://www.youtube.com/watch?v=5hrklmNilNc

 

[DemonNite]

Xenogears
Faraway Promise

Chrono Cross
Reminiscing - Unerasable Memory
The Girl Who Stole the Stars

Yasunori Mitsuda is awesome

 

[bernardobri]

"Sorrow" by Harry Gregson-Williams - MGS4

http://www.youtube.com/watch?v=TOSXygaUxYk

 

[TranceKuja]

Romantic: Love Grows from Final Fantasy VIII.

http://www.youtube.com/watch?v=NBWCTYE3Dcc

And obligatory sad: Aerith's Theme from Final Fantasy VII. Doesn't need a link, everyone and their cat knows it.

 

[VeryGooster]

"Unforgotten" from the Halo 2 soundtrack, volume two:
http://www.youtube.com/watch?v=MXLNB2K-YA0

"Theme of Love" from Final Fantasy IV: Piano Collection
http://www.youtube.com/watch?v=PSRj76Fy2Tk

 

[B.K.]

Arc the Lad II

To Tomorrow

Xenosaga Episode III

Hepatica#3~I Believe in You

 

[SlipperySlope]

Personal favorites:

Silent Hill:
Room of Angel - Probably one of the best music in the Silent Hill series, not to mention one of the saddest.

Please Love... Once More - Very emotional, song played when

Spoiler

Heather's father, Harry Mason, was murdered

Final Fantasy:
Anxious Heart - Music is full of despair. Will definitely remind you of the Midgard slums.

Celes (piano version) - Piano version is awesome, will remind you of

Spoiler

Celes' Leap of Faith

.

Speaking of FF 6...

Spoiler

Was Celes the only FF character to attempt suicide in the series? That whole scene was just sad.

I've seen characters give up their lives to help the party escape/progress (which is actually common in the series), but I've never seen one full on attempt suicide out of despair and hopelessness. Especially one thinking that they're the last person left alive on the planet, and the person they loved most just died.

 

[GCX]

Forgot to mention:

Lost Odyssey - Parting Forever

 

[JoeFenix]

Nier:

Kaine Salvation

Song of the Ancients / Devola

Grandma

In fact I could probably post the whole soundtrack, it's amazing!

 

[Yoshichan]

Silent Hill:
Room of Angel - Probably one of the best music in the Silent Hill series, not to mention one of the saddest.

This is by far the most saddening song.

 

[War Peaceman]

http://www.youtube.com/watch?v=6miaTf1gF4g

Just wonderful.
The Best is yet to come.

 

[Alucrid]

This makes me feel sad...somewhat isolated, yet still kinda happy at the same time. It's a torrent of emotions.

Ico - Heal

Edit: In fact I'm going to say that no song for me has ever captured the essence of a game more so than that song right there.

 

[Solune]

No Chrono Trigger makes me sad.

Chrono Trigger
http://www.youtube.com/watch?v=aQx9QaAxhk8

Xenosaga 1
http://www.youtube.com/watch?v=7uKyELmAKJw

Xenosaga 2
http://www.youtube.com/watch?v=nZBT37NtNZg

Secret of Mana
http://www.youtube.com/watch?v=cjxtV20zy6s

Lufia 2
http://www.youtube.com/watch?v=taYbZWq-fdc

 

[ViolentP]

FFX - Via Purifico

http://www.youtube.com/watch?v=J_JiRpDJJRU

 

[yencid]

most of the neir soundtrack could be put in here... its amazing <3

 

[ULTROS!]

Here's another despair sounding one:

The Man Who Is Torn Apart

 

[Kowak]

Never Forget from Halo 3.
MGS Peace Walker "Zero Allies!"
amazing track really!

+1

 

[Leonsito]

Chrono Trigger - 600AD

 

[NoRéN]

Chrono Cross
Reminiscing - Unerasable Memory
The Girl Who Stole the Stars

Dream of the Shore Near Another World

 

[JoeBoy101]

Max Payne 2 Theme Song.

Well that was quick, next?

 

[Danielsan]

Shadow of the Colossus
Epilogue - Those Who Remain

God damn.
Listening to it now, this soundtrack is beyond amazing.
Nothing comes close.

 

[VeryGooster]

All the MGS posts reminded me of this one from the first Metal Gear Solid, "Enclosure."

http://www.youtube.com/watch?v=G4UspBs3DGQ

 

[flyover]

Xenosaga Episode III

Hepatica#3~I Believe in You

Hell yeah. I also love this version...
http://www.youtube.com/watch?v=uV_g76ThygI

...and the Febronia theme...
http://www.youtube.com/watch?v=VsSMBfguQAY

But my favorite Xenosaga piece is Xenosaga II's "I Am Free"...
http://www.youtube.com/watch?v=pPOy9kuerqs

It's amazing, but so brief, and -- unlike most of the other themes -- it isn't reprised throughout the game, which gives it that much more impact.

(And I can't argue with anyone posting tracks from SotC, either.)

 

[RefigeKru]

The Prologue - To The Ancient Land is better and sadder, which is odd since there's nothing particularly sad about the beginning of the game, but it helps set a nice melancholic tone.

The saddest song in a MGS game is like... Way to Fall, but I don't think that counts. Now, Debriefing... *single tear

Way to Fall damn near broke my heart.

 

[disappeared]

Letters.

The beginning of the game, and it sets the mood perfectly.

 

[GDGF]

I want to post the entire Final Fantasy 6 soundtrack.

 

[BarrenMind]

Lost Odyssey - A Sign of Hope

 

[thestopsign]

No Chrono Trigger makes me sad.

Chrono Trigger
http://www.youtube.com/watch?v=aQx9QaAxhk8

Xenosaga 1
http://www.youtube.com/watch?v=7uKyELmAKJw

Xenosaga 2
http://www.youtube.com/watch?v=nZBT37NtNZg

Secret of Mana
http://www.youtube.com/watch?v=cjxtV20zy6s

Lufia 2
http://www.youtube.com/watch?v=taYbZWq-fdc

Damn that Lufia 2 music is fantastic. Watching the ending of the game and listening to that music it's almost hard not to cry.

 

[Fimbulvetr]

Romantic: Love Grows from Final Fantasy VIII.

http://www.youtube.com/watch?v=NBWCTYE3Dcc

About time someone suggested the only good version of Eyes On Me.

Orchestra Version: http://www.youtube.com/watch?v=9QYy-sj_Q-k&feature=related

 

[jay]

Requiem for Lutz - http://www.youtube.com/watch?v=hIOxeLblCAI

And I want to post Her Last Breath but the stupid title of the video on youtube contains a spoiler.

 

[Micius]

Damn that Lufia 2 music is fantastic. Watching the ending of the game and listening to that music it's almost hard not to cry.

Agreed. The ending to Lufia 2 was one of the few times gaming has managed to reduce me to tears. This just reminded me of how much I'm anticipating the NDS remake.

 

[Gaz Pwnage]

Lelianna's Song (DA:O)

http://www.youtube.com/watch?v=JbLdb7-VUQw

edit - possible spoilers in vid description, do not expand

 

[revolverjgw]

Mother 3 has about a dozen heartbreaking original tunes, and great use of an Erik Satie track

MGS Peace Walker "Zero Allies!"
amazing track really!

Oh fuck, this game just went from being my most wanted game ever to my most wanted thing ever

 

[Kyosuke]

Baten Kaitos Origins - Le ali del principio

The whole soundtrack is amazing, but this is one my favourite - absolutely perfect for the scenes it is used in. Also, according to the liner notes, the singer is Motoi Sakuraba's daughter, who was 9 years old at the time.

 

[Sinatar]

Max Payne 2 Theme Song. http://www.youtube.com/watch?v=wGvwmZmFi0w

Well that was quick, next?

There's the thread winner right there.

 

[Randy]

Garnet singing

 

[BrokenSymmetry]

Sad, romantic, mysterious:

Bastila Shan's theme from KOTOR (a.k.a. "Taris apartment")

 

[CruxisMana]

Professor Layton and the Diabolical Box - End Theme.