Too many old school games to count, some in the arcades some on 8bit, some 16bit. A lot mentioned above already. I would say Capcom's Maximo on PS2 was tough, Capcom's Megaman 1 on NES, Ghosts and Goblins, Castlevania 1, DMC3 on Dante Must Die non-greatest hits version, Ninja Gaiden NES 1-3, Ninja Gaiden Xbox, etc. I beat them all though, but they were tough, but I never thought this was the hardest game I ever played! Games aren't hard, it's just a matter of how much time you put in. These days though, the devs want you to finish their games so the difficult on normal is really like super easy setting, and Hardest feels like Normal to me.
I don't really have a hardest I have ever played, but I play a lot of hard games. IMO, the majority of today's games are incredibly easy. Even the typical games I play, I beat on the hardest settings like The Last of Us, which is how I got that Platinum. That's how I got a high gamerscore and trophies, beating games on hardest settings...all from my training with old school games and arcades. Rockband, Singstar, Dance Dance, and Guitar Hero had some tough things going on in those games on the hardest settings (Expert).
My problem is staying interested in a game. I usually get bored these days once I figure out the game, they are too easy. Devs really have to keep it compelling to keep me in it. I loved how for instance in the old 8bi days the Megaman games you acquired new powers and then the end began. There could be some very difficult games that I just had no interest in as I don't play every genre. I don't care about racing, sports, or golf games for instance, but the ones I played were easy to me against friends that owned the games.
I'd say the toughest I ever had was against pro players in fighting tournaments years ago, and I even won a few of them. Fighting games are easy against the A.I., but playing in RL with hundreds of people behind you screaming, it's pretty intense.
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