The first "so bad it's good" game I can think of.  It's happened with movies but never with a game.  How strange that I want to keep playing it while bitching about it.  What is even good about it that keeps me coming back.

X-Men Legends 2 on PS2. The game-crashing bugs were all avoidable, so that wasn't too bad. Glitches also made some powers way better or worse that they were supposed to be, but Storm and a few others were stupidly overpowered already without them.

I played bethesda's games so just take your pick of whichever one you want. I kept playing them because there's really no other comparative offerings from other devs to bethesda's elder scrolls or fallout series. The day someone does will probably be bethesda's downfall.

DKC3 and pokemon yellow.
in those cases the cartridge didnt save. i had to play from start and finish in a single play.

SNES chessmaster.
When we start to win from the AI, the AI take too long to make their move. Man, i waited 6 hours for a AI move.

I once had a messed up copy of Crash Bandicoot: The Wrath of Cortex for the GameCube.

Everytime the game loaded a new level or something, there was around a 50% chance that the game got a disc error, and I would have to reset the console and sit through the long loading screens just to boot up my save file (which is one of my major gripes about that game).

I must've been one patient kid back then, cause despite having to sit through a crap ton of disc errors and long loading screens, I still managed to beat the game.

Mercenaries 2.

If I did, it was probably a flash game.

Sonic 06... I didn't have a good time playing it, that's for damn sure!

Fallout new vegas, kotor 2, aliens vs predator 2 which took a lot of work to make playable past the second level.