The only chatroom roleplays I can stand are ones from ShamChat, and only if I'm playing as Death. You get some interesting as fuck characters going through that thing, acting as if you were about to take someone's soul from them. I once had to explain timelines and shit to a female Hamlet in character. Shit was hilarious.
Then there was that one time I played as Shenron Lite and turned Dr.Jekyll into Mr.Hyde. He asked for new lab equipment and I dropped a magic sandwich in there with it 'cus I was bored. Then we had an interesting conversation about how lame he was. Then he ate the sandwich. It was fun.