Every so often, I decide that I need to replay Final Fantasy VIII, and then during the course of playing it, remember what a horrible game it is in terms of both characters (seriously, Squall, seriously, you mopey twat who gets everything handed to him?) and game design (oh my god, a boss is threatening this country, better spent half an hour sucking magic from it's ass) and end up stopping around Disc 3, every time.
Sim City 2000 also gets an honourable mention as something I always kinda liked, but since I found Tropico 4, it kinda shot SimCity 2000 in the chest and dumped it's body in a bathtub with acid.
Also, Fallout 3, but not because it's amazing. It's because my friends always talk about it, so I load it up thinking "Right, THIS time I'll figure out why it's so good" and I still don't enjoy it very much.