Amelyssan in Throne of Bhaal, if you've installed the Ascension mod. Unfortunately for her, she did not reckon with the power of Uninstall.
Also, winning the Royal Rumble match in Wrestlemania 2000 (ah, the N64!) was unadulterated hell. The match lasts until either you or 29 other people were eliminated, usually upwards of half an hour. One reversal, one percentage-based outcome against you, one move being counted as hitting you when you were remotely near the ropes, and you could be eliminated through no fault of your own. The only saving grace was that it wasn't mandatory to win it in story mode.