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[Frimaire]

For my list out of bosses I have personally fought, it would probably be:

1. Satan from SMT: Digital Devil Saga 2
The only boss I've ever needed to use a calculator and notepad for.
He has a tonne of dirty shit, like

Spoiler

a move that insta-kills if your party isn't fully buffed, a move that has a high chance of charming your whole team, rotating elemntal weaknesses

, and worst of all,

Spoiler

a full heal that he uses once his health drops below a certain threshold.
You have to keep track of his health and kill him in one bust at the end.

I hear the secret boss in DDS1 is actually way harder, but I didn't even wanna try that...

2. Laurence from Bloodborne DLC
Already brought up in this thread a few times.
I was on like my second NG+ when I fought him.
The hardest boss I've ever fought in any Soulsborne game. I definitely died over 50 times, possibly over 100...

3. Belzaboul from SMT: Devil Survivor.
Not actually an insanely hard boss, buy hey, it was my first SMT game.
I legit dropped the game for like 5 months before I finally came back and beat him.

 

[Mr. Poolman]

Oh no...

The pain... the frustration... it is all coming back.

 

[TraBuch]

They've obviously never played Fight Night Champion's great story mode.

Isaac Frost is a fucking asshole and I had to cheat to finally beat him.

 

[Artdayne]

Bleeding edge, world first progression level raiding in WoW is probably the hardest thing, not particularly tied to a specific boss per say though there are some clear standouts. There's a huge difference between raiding something where you're severely under geared comparatively and have no video or strategy to use other than your own and when most people are raiding the content and have access to much better gear and a video to copy. I stopped raiding half way through Warlords of Draenor so I can't speak to the difficulty of the more recent fights Yogg-Saron, Lich King, Ragnaros, supposedly Al'Akir (before the bug was fixed according to someone in Paragon), Imperial Vizier Zor'lok (before the nerf), Lei Shen, Siegecrafter Blackfuse.

Heroic Ragnaros took Paragon something like 700+ attempts before they killed it. A very highly mechanical fight that had very severe DPS checks. There is no single player game fight that I've seen that comes close to approaching the complexity of some of the harder raid bosses in WoW. At the cutting edge of progression you are required to maximize your damage to the 95+ percentile while limiting the damage you take as much as possible, keeping an eye on the health bars of the 24 other people you're playing with and using raid cooldowns if needed or when asked, maximizing DPS cooldowns around boss mechanics, when bloodlust is used etc and above all survive as long as possible because dying early during progression greatly impedes progress for the entire group.

 

[Van Bur3n]

was this patched or did I unintentionally cheese this? Played it last week and the dlc, just stayed behind her and the fight took ~2 minutes without losing less than half a health bar

if anything, surprised lady Maria wasn't on here, was the boss I was stuck longest on

Did the same thing with Ebrietas and she died in less than two minutes on the first try. Don't know why some people have as much trouble with her as they do. She is completely helpless from behind and getting behind the enemy is like the first thing one should try. Combat 101.

 

[Gunblade47]

No Sans from Undertale genocide run?

Personally would put the FFXI boss above the WoW one.