Obligatory: the early 2000s web site 'aoliza' which turned vanilla Eliza loose on AOL Instant Messenger, with predictably hilarious results demonstrating that the Turing Test was beaten decades ago[1].
Holy S! How did I not know about this?! (I curate ElizaGen.org … where this is immediately going! DM me if you want cred by your rn on the elizagen news post; my rn and landline deets are in my hn about.)