Deus Ex and Dishonored without being detected are my best trophies I'd say

Hardest game by far is Rayman on PS1. I had nothing else to play for a year after getting my PS1 (got a ton of games at the start but burned through all except this one). Oh man I HATED this game by the time I finally beat it and will never replay it.

Good on you. I wrestled with it from a gamesmanship standpoint, but like I said, I did it. :(

Here's a weird story.  When I first beat GoW3 on hard against the cerberus and satyrs I had a hell of a time.  Was probably at it for a couple hours.  THEN I got the remastered version and was mentally preparing myself because I knew it was coming this time and...beat it on the first try.  Yes I'm sort of bragging but seriously it was hilarious to me when I beat it because I had been dreading that encounter after my memories from years earlier were much like yours.

Asking me if using a Game Genie counts as legit beating a hard game is like asking me if watching a playthrough on youtube counts as legit beating a hard game too.

Hard to say without direct comparisons of difficulty.

Halo 2 solo legendary was intense.

Age of Mythology on Titan with various maps to change the difficulty was insane.

ROTK IX is hard on weaker factions.

etc. but these ones obviously are closest in my mind atm.

I beat some legendarily difficult games in the NES era. Some, just thinking about stress me out. I'm gonna say Castlevania iii with every character except Trevor by himself.

Adventures of Bayou Billy had the reputation of being one of the hardest games ever but it wasn't that hard. Just different from other games of the day.

Astyanax! One of the last NES games I ever bought. Good memories of that one!

Probably one of the Modern Warfare games on Veteran or Uncharted games on Crushing.

I can't think of a good answer for this one. I rarely complete games on the hardest setting, as I find it too frustrating. I've beaten some games that were very difficult regardless of the settings, but none come to mind at the moment.

I remember, as a child, getting near the end of the final level in Cobra Command (Sega-CD) and never being able to pass a certain point. I tried many times, as it was really close to the end. But, I couldn't do it. I got in a lot of trouble for cussing at the TV. I believe my mom took the game away after several of these incidents. I recall the rest of the game being challenging, but not terribly so.

Ninja Gaiden II on NES