joshdad: I'll start with some of my earlier gaming memories. When I was about 12 the Atari 2600 was the popular system, and my brother and I had quite a few games for it. There were a couple of games that we just could not seem to figure out. The ones that come to mind are:
Raiders of the Lost Ark and E.T. - we spent quite a bit of time with those games, and I don't know if we ever actually beat them. BUT, the worst game of all that we had was a game that I think was called
Sword Quest. I remember that there was actually some kind of competition offered by the developer that if you could beat the game and take a picture of the final screen you would win a lot of money. We must have spent 100's of hours trying to play that game, and never even had a clue what we were doing. We beat a lot of the puzzles, but never really knew why. One of the most confusing game I've ever played.
A bit more recent, I would add
StarCraft Brood Wars (the expansion game). I beat StarCraft a few times, so I figured I should do OK with the expansion. I could never get past the first scenario. Never has a game made me feel more stupid that that game. It seems like you are given about 10 minutes to try and prepare your forces to face countless waves of enemies that include some of their best units. Bad, bad memories of that game.
More recently I would probably add
Portal. I just couldn't figure out the whole where to place the hole concept without racking my brain to the point of getting a headache. What made me feel even more stupid is that my 12 year old son jumped right in, and figured it out within seconds - UGHH.
I would also say
Spellforce. It started pretty good, not too hard, but pretty soon, I was getting so confused trying to find ways of beating the hordes of enemies (without getting quickly slaughtered) that I felt really dumb. Seems like a fun game, but just not one for me.
I had a couple of the Sword Quest games and remember the competition. It wasn't just you, the games just didn't make any sense.