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Does the game explain how you get the different prefixes to your dead heroes? Like Feeble Sir Dude or Useless Sir Dude II? and do they have anything behind them?
I'm not sure, but I think it's related to gold total. I think "Legendary" happens when you beat any of the four bosses.
It may also be related to the number of enemies slain. I've noticed that the more I kill, the better the title.