IMO, the worst game I've played has to be 18 Wheels of Steel: American Long Haul. Sure, I like the concept of trucking around cities, but they're usually all the same except for layout, businesses, and maybe some of the key landmarks of each city (but I can't remember). The part that made this game terrible is that it was impossible to unload the truck. Was this the main point of the game, if everything was pretty easy?
Oh, and I forgot to mention... isn't it one of the poster children of the bloatware known as WildTangent?