That Boss You Never Wanted To Kill

[EHKOS]

In Crash 2 I never wanted to kill N. Gin because he was so fun to battle.
I also didn't want to kill that paupers drop lady from Bioshock 2 so I never did.

 

[ZehGeek]

Another one for The Boss from MGS3.
Ironicly, after I beat Liquid Ocelot in MGS4, I felt really bad about killing him.
(Don't read unless you've played MGS4 or just don't care)

Spoiler

He did like the noblest thing ever by pretending to be Liqiud, and fooling the Patriot's AI, but his mission was a success so I don't think it was all that bad.

Gray Fox in MG2(Metal Gear 2, not MGS2), specialy after playing MGS for the PS1 then playing MG2.

Spoiler

When Fox sacraficed himself for Snake by holding off REX and destroying the Raydome so Snake could go after Liqiud, and his final speech just sent shivers down my spine, specialy when I think about it. Heck, I'm getting them right now. xd

Gee, those are the only two I could think of. I'm sure there's some more, but for the life of me I can't think of any. Only a few anime deaths. ;-;

 

[Teh Ty]

Obvious answer: GLaDOS
Not so obvious: Either Gruntilda from Banjo Kazooie, or The final Bowser from Super Mario 64

 

[PeppersResort]

It would have been nice to join Sephiroth in FF VII and kick Shinra, the Turks, AVALANCHE, Aeris and even Yuffie's hometown of obnoxious ninja pickpockets off a cliff. It was so disappointing you had to agree to save the whinging, gormless civvies and in turn, the world.

 

[exarkunsith]

Jack of Blades for Fable, loved the voice and he just looks awesome.

 

[Vivace-Vivian]

I dunno if she counts as a villain but

Spoiler

Cybil Bennett

from Silent Hill

She wasn't evil. I know there's a way to save her but if you don't find it... terrible.

 

[JakBandit2208]

Saren in Mass Effect. So many shades to this character: 1)he hates humans, but only because his brother was killed in the First Contact War, 2)sold out to the reapers, but only because he believed that he could negotiate some kind of truce to save organic civilization, 3)allowed himself to be cybernetically linked to sovereign, but ultimately gave his life in an effort to redeem himself (if your charm or intimidate was high enough). He was ruthless, he was cold, he made dubious decisions, but he was not evil. Simply an honorable, flawed man who made the wrong choice. Saren was practically the definition of a literary tragic hero.

SAME here. That's exactly who I was going to say.

You both beat me to it...