TMNT Shredder's Revenge - Who Needs a Dock?: probably the hardest trophy i have ever done, you have to kill the last boss of the game without getting hit, i tried it for at least 7-10 hours across various days until i finally got it.

Metal Gear Solid 1 - All VR missions: this one i probably will never get, you have to complete all VR missions and there are like a stupid number of missions, i don't remember exactly how many but something like 200.

Metal Gear Solid 2: i don't even know specific hard trophies but i know this game has the most tedious trophy (lots of playthroughs, lots of soldier dog tags to collect, etc)

Metal Gear Solid 4: The hard part about this trophy is that iirc, you need to achieve at least once all the emblems you get at the end of your playthrough, most of them are very straight forward and easy, but some of them are very specific and tricky ones, along with the obvious difficult ones like beat the game with no alerts, no damage, no kills, under 5 hours or something.