Back within the first 3 or 4 months after ponibooru killed itself I took the liberty to be the annoying idiot of this site. But I took care to follow the rules (and still do) so I wouldn't get banned. Especially since there weren't many other users here at the time (including moderators of course). It was mostly just some of the old folks from ponibooru. So I decided to "introduce" myself to them as presenting myself as a moron with no sense who rambles too much and doesn't know what he's talking about, mainly through idiot comments on uploads deemed "controversial" by the community.
Uploads involving: 9/11 jokes, pinkiepony, the lyra plushie, pony haters, tumblr drama, and feminazis, were my main targets
People would comment about this and that, whatever, and have their opinion. But I troll them in any way I could (within the rules). What worked the best was to reply to their comment and completely disagree with their opinion (even if I actually didn't agree with what I was saying) in a way that would piss them off and make them type endless paragraphs in response.
I didn't even find it entertaining at all, I would just do it.