While there are MANY bosses that can fit into this category, this is the most elite of the elite. Not only would you not fuck with these bosses, but you would tuck tail the minute you saw even a hint of them coming your way.
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Professional boxer; ear biter; convicted rapist; head tattoo bearer; cause of more broken controllers in history than any other boss
Big unknown alien; causes massive destruction and armageddon; not fond of red spiky hair and/or time travel
There's no way out. You'll just have to fuck it.
Giant brain...with spikes; creates power suits for women; have to be blessed in order to defeat it
Malevolently evil computer program; hates humans; believed to be HAL's secret lover
Giant white-gloved hand; refuses to use hand sanitizer
Manifestation of evil; attached to you; voiced by Mike Patton
Lord of Terror; likes fire; hates you
Fighter from Thailand; long reach; TIGER...DEEESTRUCTION!!!
Most powerful Elder God; has tentacles on face; will crush the fuck out of you...with his pinky