I've played some awful games in my time but I think Superman 64 tops it. I had a friend in second grade who had the X-Men game for the Nintendo and he brought it over one time to play with me. The game was shit but at least I was playing with somebody which has some degree of fun to it regardless of what game you're playing. Superman 64 was a rental to play by myself... and yeah, seeing essentially the first 10-20 minutes worth of game content and repeatedly playing it ad nauseum because the controls are awful(and of course the whole premise of the gameplay) takes the cake for me.
I've played other bad games like Friday the 13th, Mario is Missing(which I liked when I rented it to be honest) and Shaq Fu(again with a friend), but given the circumstances I think Superman 64 takes it.