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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@MangoKangaroo
Crypt of the Necrodancer
The characters are difficulty levels, some with additional rules.
It’s a rythm rpg, lore character #1 can miss beats, collect stuff, etc.
Lore character #3 can’t miss a beat or miss and can’t upgrade health, so you always die in one hit.
When I beat the 4 chapters with that character I was done :D