There isn't much about it in the wonderful show know as My Little Pony: Friendship is magic, and with what precious little there is, is rather vague and not very insightful. The little we know is that or lovely Dissy reined with a cotton candy fist, and did so for sometime. What we don't know is where Discord came from, exactly how long it was before he turned evil (or if he just outright was), his motivation, how ponies other than Luna and Celestia took it, how ponies recovered from his reign, and how he didn't go insane while being stoned for 1,000 years, and the list just goes on and on and on...

So my question is what you guys hold as head-cannon for the Discordian Era?

I personally think he originally got along with our fair princesses, and something tipped him into villainy, and that during his "stone age" he found some way to entertain himself, kinda of like in the Fic Keepers of Discord

3752098
I've always seen Discord as a natural counter point to the ponies. They (after the unification) fall under a clearly Lawful alinement and seem to force that on everything around them, even the environment. Discord is harmony's was of trying to restore it's self, but he is simply the other end of the extreme.

As far as his "Stone age" I expect he spent most of his time plotting and planing. He might be chaos incarnate, but he's shown that he can play chess master with the best of them.

3752098 I agree but I think its more like "Wicked" where to achieve his well intention goals he had to do away with normal morals, another theory is that he became the avatar of chaos just like the main 6 became the avatars of the elements of harmony. Thus he just took his place as the spirit of chaos.