My personal WOAT contenders:
Saint Cornelius - Born to a playboy bunny and his real father might be Peter Cetera. He had two different personas: the gruff poonhound who needed several more dicks for all the pussy that got thrown at him (The Bore/GAF persona) and the batshit insane nutter who followed enjoy bell woods around (Opa Ages persona). He'd hop from one place to the other like somehow there weren't motherfuckers who went to both sites. We all know and love the redWOOD story. Then, in an about face, he turned from poonhound to responsible family man with a kid. I don't know if it was his kid or if he just shacked up with a single mom. While he went through this new revelation here, in OA, they created a subforum for just him to scream and rage about enjoy bell woods. At one point or another, everyone was on his nuts or riding his dick.

Futami - He was a troll but was completely uninteresting. He'd basically make up shit about being rich until he let slip that he still lived with his mom. Like Corny, futami pretended he was a pussyslayer but he posted constantly on the forums. He'd inevitably wear out his welcome where he'd come back under various alts, usually based on a somewhat mainstream rapper or singer, such as Phonte and Tony Sunshine. He'd pretend not to know who futami was but basically picked up wherever he left off, same posting styles, same stories, etc. In the early OA days, he met with Alphasnake and claimed to have been packing heat. He's probably still posting on GAF and OA under some alt.