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[Raven117]

Pre-Nerf Consort Radhan: Elden Ring (This broke me. I felt nothing but relief...and honestly, It may have killed my interest in video games)
Defiled Watchdog: Bloodborne (my build was just not geared toward him)
Seikro: Isshin (just for how freakin long one had to be perfect to win).

 

[Rivdoric]

50% of Sekiro bosses to the point that it was exhausting and not rewarding in the end, juste pure angriness.

 

[deriks]

Intensity I guess that Sekiro has a lot

But I can say that when I got into Sam in Metal Gear Rising... Wasn't just about difficulty but the whole situation in their world

 

[Hawk The Slayer]

In no order and just to list some really cool and epic ones.

RE1/RE1 Remake - Tyrant the Ultimate Life Form
RE2 - Super Tyrant/G3/G4/G5
RE3 - Nemesis in the Clock Tower with Carlos and later at the dead factory with Jill
RE Outbreak - Thanatos 2nd form
Final Fantasy IV - Zeromus as well as most bosses
Final Fantasy IX - Trance Kuja and Necron as well as most bosses
Final Fantasy X- Final Aeon as well as most bosses
The Legend of Zelda Ocarina of Time - Ganondorf/Ganon
The Legend of Zelda Majora's Mask - All the Bosses
Ratchet and Clank Up your Arsenal - Bioblitorator
Warcraft 3 - Archimonde
Starcraft - Overmind
World of Warcraft - Lots and lots of bosses
Stellar Blade - the non robot final boss choice
Elder Scrolls 3 - Modded Dagoth Ur and Almalexia
Elder Scrolls Skyrim - Modded Alduin, Harkon, and Miraak.

Many more but can't remember at the moment.