A cleverbot like program with a doctorish theme
This program was interesting when it came out because, if used with a selection of Sound Blaster sound cards, it used audio vocalizations for the text on the screen. You interacted with the program by typing your queries, which were than analyzed and the AI answered you back. Of course, the parser was not too highly developed and most of your queries were answered rather mechanically, following a pattern that becomes visible quite soon. Also, the program did not seem to remember your older question and his own answers and this lead to some amusing situations, though, most of the time, you were offered some stock replies that turned boring fast. But, for the time, the purpose to showcase vocalization of texts was managed relatively OK, so in that respective the program did its bit. So, I would recommend you give this thingy a try only if you're interested in the evolution of text to speech software and also, if you want to see what was the state of AI mimicry of natural conversations, back in 92.
