Pilotwings - talking the original for the SNES/SFC here. I remember my brother was really good at it, but I just sucked. I went back to it years later after playing Pilotwings Resort and finally managed to play through the whole thing. Awesome classic.|
Planescape: Torment - THAC0? Why is better defense a lower number? Not at all used to D&D ideas, and with a really broken grasp of English, I really struggled with this game at first. I still think that era of games may have been designed better than the nightmare interfaces in the old PC RPGs, but could have done a better job at introducing D&D concepts into the game world in a reasonable and more video game-y way. I'm glad I did, its one of the greatest RPGs of all time.
No One Lives Forever - as said before, I have real trouble with modern look and aim FPS controls. I couldn't get anywhere for the longest time in this game. I think I had to repeat the first few missions over and over again for about 10 hours before I get good enough to proceed past the next and kept on hitting blocks in my skill level. It was worth it though.
Final Fantasy - the original, old, old Famicom game. I played it after the PlayStation ones and for some reason to my young mind, I assumed it had the same control as God Slayer/Crystalis, another Famicom action RPG, which had been my introduction to older RPGs. In that game, in order to open a treasure chest you have only to bump into it. I thought that was the same for Final Fantasy and so I couldn't get past the Marsh Cave forever, because after I beat the boss, I couldn't get the crown in the chest. I just assumed you had to bump into it. Took my five tries to realize you have to press the A button by standing next to it. In my defense, I was really very young at the time.
The Legend of Zelda - I remember thinking this game was the stupidest thing ever as a little kid. Why on earth had this series gotten popular? Coming from A Link to the Past, Link's Awakening and Ocarina of Time, I didn't get it at all. When I finally understood how to play it, I of course, grasped the secret of everybody and now I love it.
Ridge Racer - for the longest time I could not figure out the drift mechanics in this series, it took until Ridge Racer V till it finally clicked with me. Until then, this game was just Asobit Racer and you played it in the arcade to smash into things and have random fun.