Most of my gaming struggles were in the 8-16 bit days, just an era of console and arcade games designed to destroy you. But I suppose that was the norm.
For more "modern" games.
Alma in Ninja Gaiden (vanilla) took me an excessive amount of tries the first time. ON NORMAL lol. I'm no stranger to difficult games, but that was the only time I almost gave up on a game I liked. I went at that shit for days, wouldn't be surprised if it was in the ball park of 100 attempts. In hindsight not even sure why I struggled so much, eventually got to where I could beat her on Master Ninja without taking a hit. But that one always sticks with me.
The entirety of Ninja Gaiden 2 on Master Ninja is an exercise in insanity, I'll never do that again. About a 15hr game, but took me about a month just grinding down one section at a time. Might be the hardest game I've played.
More recent years, nothing like that. Had the occasional struggle in Demons Souls (my first Souls game) or Nioh, but nothing that stands out. Suppose Father Gascoigne took me to school more than I'd like to admit, but nothing too crazy.
Most recently, some of the Doom Eternal slayer gates on Nightmare. One in particular took me dozens of tries. They're about equal to Ninja Gaiden 2s tests of valor on normal mode. Very challenging, but within reason.
Outside that, just challenge modes in games that you're supposed to grind at. Angel Slayer, Witch Trials, Bloody Palace, Mission Modes, etc. but they're like that by design unless you're one of those gaming mutants.
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