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Hardest Boss Fight?

I'm getting flashbacks of trying to beat all the bosses of the main game in Metal Gear Rising: revengence on hard difficulty without taking a single hit...All for some shiny silver trophies. I vividly remember spending one weekend trying to clear the Monsoon fight under these conditions, and I'm glad I eventually got there in the end. Final boss was challenging too, especially consider it had multiple phases to it and if I took a hit, I would've had to start from the beginning again.

Terramorphous the Invincible raid boss from Borderlands 2 and Hino-Enma from Nioh are a few examples of more recent bosses that I found quite challenging to clear solo.

Oh dear god Monsoon...
 
Fucking Lingering Will bro.
 
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God I fucking hate Dark Souls II's bonus bosses in the DLCs.

Also, any of the gimmick Souls bosses without the items required to fight them fairly (eg. the eye for the tiger next to the entrance to the CotIK DLC, Kalameet getting shot down by Gough first, etc.)
 
.....yeah so Gentle Eel in Tales of Graces f is literally the only boss in that game we've ever had to bump the difficulty down to easy in order to beat

he is not gentle, he is a bloodthirsty murderer in disguise

I remember the one time I tried to cut off Kalameet's tail to get the Obsidian Greatsword

did eventually manage to get it, but I'm not ever doing that again lol
 
I couldn't beat "the end" in Metal Gear 3. Lots of the fight revolved around sniping, which I'm not good at.

Ah, good times. You could also have opted to wait him out. He dies of old age eventually.

Also, Colonel Radec on Elite difficulty.
 
Two words: Mega Magic.

Bravely Default fans will understand.
 
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