Big Rigs: Over the Road Racing. Has the worst metacritic score ever (or at least it did when I last checked). The game was just really poorly made but the fact it had so many stupid flaws made it awesome. There was no sound, half the maps crashed the game, your opponent never left the starting line (so you never lose), there was no difference in friction between on road, off road, or inclines (yes you could drive up vertical hills), the in-game "exit to windows" took you back to the main menu, there was no limit on the rate of increase of acceleration when reversing (meaning you could reverse at the speed of light, then faster), you could drive through buildings and scenery (bridges were hilarious), it sometimes glitched when you started a race to instantly win since you were just *past* the finishing line, and when you do win it says in big bold letters "YOUR WINNER"
They released a patch to correct some of the games issues, all that was fixed was that the opponent actually "raced you". However, the opponent always stopped just short of the finishing line meaning that, still, you could never lose.
Oh and the game manages to take up at least 50% of your CPU regardless how good it is.
When I first played this I just couldn't stop laughing. I open it up every now and then just for a joke