There have been two occasions when a game has been so hard I've felt like crying.
First, the Defiled Amygdala boss from Bloodborne. I must have tried it fifty times, at least. It was probably more like a hundred. It honestly could have been more. It's a completely unfair fight against a massively dangerous, slightly unpredictable boss in a confined area where you can barely take one proper hit or you're dead and the boss requires probably a hundred hits. The second phase of the boss requires you to get right up close and hope it doesn't do certain moves or you're instantly dead. I'm sure there must be better strategies but for my build, that was that. The actual winning fight probably took me fifteen minutes or something. There were times when I was so angry and frustrated that I wanted to cry and kick the fucking telly in. It wasn't even the difficulty per se, it was the sense of the passage of time and the fading of my reactions and co-ordination and confronting the possibility that I just might never be able to do it and that over time, my chances of success were actually becoming less likely, from a physiological perspective while my desire and obsession to overcome this only grew stronger. Coupled with the themes of the game, and the morbid end of certain NPCs, this was really heavy going. When I finally did it, I annihilated the rest of the game and I've pretty much left it alone ever since.
The second was Ikaruga. I only got into it last year and finally understood how to play it. The reality is that there's one way to play it - perfection. It's not really a game about creativity or expression, it's about understanding the strategy and executing it. It's like a puzzle game in terms of your strategy and a bullet hell in terms of movement, but it's also like a rhythm game with the polarity switching and use of missiles. It reminds me of drumming in that you seem to be doing different things both independently and interdependently. I'm a really shit drummer. I decided I would keep playing until I hit S Class on Chapter One. And so I practised. I practised and practised and practised and I played it for several weeks. I thought about it a lot. I dreamed about it. I daydreamed about it. I visualised the run. I knew what I wanted to do and I could not do it. I simply could not do what I knew I wanted to do and what I tried and tried and tried to do. I was improving all the time, through C, C+, B, B+, A...but every improvement was so painful and so dependent on something beyond my conscious control. I just kept going and going and I gradually built more and more fine movements into muscle memory. It was a really intense time and in some way, I felt quite overwhelmed by it. It was like the Bloodborne feeling I described above. I basically had to do it. I reached a point though where I simply reached a plateau and no matter how much time I put in, I couldn't execute what I wanted to. Even the easy sections started to fall apart. I genuinely felt like my nervous system was slowly dying. I could feel age irreversibly gnawing at my twitch fibres and brain cells. An infinitely slow but inevitable petrification of my faculties. And then I fucking did it. Max 90 combo. 3.01m points. S Class. And I did it again and again and again and then I did it every time for a few days. Probably a dozen times. Max 95 combo. 3.6m points. That'll do. I felt such a weight lift from my shoulders and I never want to play it again and I never want that feeling again.