Neverwinter Nights/Awesome


 * If you manage to beat Morag in the first game without reaching level twenty, it's already pretty awesome-- but when the finishing blow is landed by your halfling henchman while you're running away and pissing yourself in terror, that's a Crowning Moment of Awesome.
 * How about subjugating the ruler of the Eighth Circle of Hell, conquering it with him as your lackey, and turning it into a realm rivaling that of the Ninth Circle. And of course when you die, it's highly probably you'll just continue to rule into the afterlife and beyond.