Be it a game that’s difficult in its entirety, or a particular challenge in a game that you just couldn’t complete.
For me, there are three that come to mind:
Super Hostile: Waking Up (Minecraft Custom Map, Hard difficulty). That damn water section…
Terraria Zenith Mode. Coming from someone to whom Master Mode is fairly easy, this was rough.
Calamity Death Mode (Terraria). I beat DoG (this was back when a headshot was an automatic death), but I just could not click with the Yharim fight. I also think burnout was at play here because that was a LONG playthrough.
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This was me playing Ocarina of Time.
It was also me when I played Majoras Mask. Young me did not comprehend that shit at all.
I never played Majora’s Mask. Having seen speedruns of it, I’m pretty sure it would have fried my brain as a kid.