my life... >.<
Haven't given it much thought. Maybe Sekiro? Funny enough that I ended up Platinum the game %100. Must have beaten it like 5-6 times. As much as it was frustrating. It was fucking fun.
It is old, but the hardest and most annoying game I have ever played in my life has to be Chakan: The Forever Man for Sega Genesis. Easily the hardest game I've ever played and I've played and beat Ninja Gaiden, Castlevania 3, Battletoads, Contra Hard Corps among other rather hard games. This one takes the cake, it is the single hardest game I can think of that isn't a broken mess.
oofie hakaied.... :/
IGI and Delta Force.