I still remember fighting Psycho Mantis in Metal Gear Solid 1. He would read all your moves before you did them and was literally impossible to beat. He would also talk to you about the games that you had already played by reading your memory card (this was super trippy). The only way to beat him was to unplug your controller and plug it into port two so he couldn't read you moves anymore. It took me and my buddy days to figure it out... This was before Google too, so you couldn't just look it up.
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The golem from Terraria took me ages when I first encounter it. I had awful gear and I didn't know the best strategies to defeat it
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Final boss in dark souls
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Eberitas bloodborne
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Dark sonic from the sonic games
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Dark sonic from the sonic games
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the final boss when you did like the story mode on super smash brothers on the hardest mode and you had to fight that hand thing
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The jetski level in battletoads.
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The electric shock QTE in MGS: peace walker
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Any boss on dark souls...
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Ornstein and Smough. *drops the mic*
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2 girls one cup
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Crota
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Activision (still is undefeated to this day despite the hammerings they've taken from the public)
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Frank Horrigan from fo2
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Doppelganger from castlevania symphony of the night
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Apex zinogre. My most hated thing to fight. Ever.
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Either the dance off with God on that Simpsons game or Dr Nefarious from ratchet and clank 3 (don't judge, I didn't have the rihno)
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Idk that asshat at the end of heavenly sword pissed me off though
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Skorge on Gears of War 2 and Raam from Gears 1
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Prophet of Regret from Halo 2 it took me days to finally kill him
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Voracidous, bl2
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Crota on hard solo as a hunter with no galahorn
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Sephiroth In kingdom hearts 2.
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Fire Base Phoenix from Operation Flashpoint..
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Ninja Gaiden 3: Razor's Edge Your shadow clone's second form Or the masked alchemist
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i would have to say omega himself, it took close to an hour at my level. then there was jormungand in the arena conquest, ***ING JORMUNGAND! my lawn, my lawnmower ahh, dr. nefarious on hard difficulty, not even the best weapon (at its starting level), best armo in the game would make a dent or prevent some of the damage