SmarterChild was a chatterbot

Chatterbot

A chatter robot, chatterbot, chatbot, or chat bot is a computer program designed to simulate an intelligent conversation with one or more human users via auditory or textual methods, primarily for engaging in small talk. The primary aim of such simulation has been to fool the user into thinking...

 available on AOL Instant Messenger

AOL Instant Messenger

AOL Instant Messenger is an instant messaging and presence computer program which uses the proprietary OSCAR instant messaging protocol and the TOC protocol to allow registered users to communicate in real time. It was released by AOL in May 1997...

 and Windows Live Messenger

Windows Live Messenger

Windows Live Messenger is an instant messaging client created by Microsoft that is currently designed to work with Windows XP , Windows Vista, Windows 7, Windows Mobile, Windows CE, Xbox 360, Blackberry OS, iOS, Java ME, S60 on Symbian OS 9.x and Zune HD...

 (previously MSN Messenger) networks.
SmarterChild was an interactive agent or bot developed by ActiveBuddy. It was distributed across instant messaging and SMS networks. SmarterChild became very popular with over 30 million Instant Messenger "friends" on AIM (AOL) and MSN over the course of its lifetime.

Founded in 2000, ActiveBuddy was the brainchild of Robert Hoffer, Timothy Kay and Peter Levitan.