There was a fad for chatbots during the MySpace era (or at least the early-mid-00s AIM era?) too, I remember messing around with trying to build them. They were

There was a fad for chatbots during the MySpace era (or at least the early-mid-00s AIM era?) too, I remember messing around with trying to build them. They were a lot less accessible and less documented than the APIs available today though! Eg https://en.m.wikipedia.org/wiki/SmarterChild https://en.m.wikipedia.org/wiki/SmarterChild