Video games always have a pattern of some sort to work out to kill "The Boss" , so I don't find them especially hard. Annoying most definately, but not hard.
Back in my MUDding days, there were several *bosses* that seemed impossible. The MUD in question: Apocalypse V ( diku ). The *boss* in question: The Ankou . I still can't figure out how he's killed. He beats the everloving shit out of you everytime you touch him, ( he returns a % of the damage that you deal to him. ), Teleports to a GOD ONLY room when he reaches a certain # of hitpoints ( you can't teleport/scry/portal there at all ), and he heals himself something massive...
Another of the *bosses*. Not exactly impossible, but takes a group of smart/heavily equipped people to take her down... The Black Widow, Alcina.
Just reaching her room takes about an hour & half of preparation. Your group has to just about wipe out everything else in the zone to reach her. Then the fact that she's in a one-person-only room, and the entrance is small-sized. ( 5 player sizes in the game. Tiny/small/normal/large/giant. ) . She's got Cloak Of Midnight ( makes it impossible to see anything ), The same *skill* that the Ankou has with giving back your own damage, Fire breath/poison/cold breath ( any single one of those can kill in one shot. ), Paralyzes, and backstabs! To make it even better, the room is soundproof, so you can't escape out or call for help, and she'll loot your items off your corpse if/when you die. ....
There's not many things I could compare the experience to in a video-based game.
But I will say that it did take me a few hours to figure out Ruby/Emerald in FFVII. But after you've got 3x master summon matiera, 3x mime, 3x w-summon etc. etc. etc. it's pretty much a piece of cake . You can pair up the materia in such a way that after your first cast of KOTR, your whole party just continues to recast it, while absorbing back all their HPS & MPS ad infinitum. But using that setup alone with ruby got me whacked quite a few times, until I started using Alexander at the start.
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