SmarterChild: A Chatbot Buddy from 2001

By Hansen Hsu | May 29, 2025

Did you know that there were chatbots long before Siri and ChatGPT? CHM’s latest exhibit, Chatbots Decoded: Exploring AI, tracks the history of chatbots from the 1960s to today. The first chatbots on the consumer internet that came out in the early 2000s, during the heady days of the dot.com boom are an important part of the story. One of these, featured in the exhibit, was called SmarterChild.

Origins

SmarterChild was the product of ActiveBuddy, a company started by Timothy Kay, Robert Hoffer, and Peter Levitan in January 2000. After the failure of a previous startup, Kay and Hoffer brainstormed ideas for a new startup and came up with the idea to do a chatbot for instant messaging platforms. Kay believed natural language would be a compelling new user interface for computers, especially intelligent agents that could look up information like stock quotes, dictionary definitions, sports scores, and the weather in response to a written query. Kay wrote a prototype bot in two weeks, and Hoffer rounded up investment funding.

Content for the new chatbot was provided by a team of subject matter experts in New York City. The difficulty of hiring technical staff during the dot.com boom actually proved beneficial, and the members of the content team spanned a broad range of topics and interest areas and included schoolteachers, book publishers, and even a rock musician. To make it easy for the non-technical staff to write SmarterChild’s answers, the engineering team created a simple programming language that was easy for them to learn.

Education

Unlike today’s chatbots, which generate answers statistically based on training data gleaned from the internet, all of SmarterChild’s responses were written by humans, or what Kay calls “curated.” This meant that SmarterChild would not give false, dangerous, or otherwise problematic answers. Its human-curated responses were also more accurate and relevant than later machine-learning based voice assistants like Siri and Alexa, and it did not “hallucinate” by generating false information on its own like many of today’s chatbots.

How did SmarterChild work? If it did not understand the user’s query, it could respond by reformulating the query as a question of its own, similar to Eliza, a pioneering chatbot from the 1960s. But to be a useful information utility, SmarterChild needed a way to parse the user’s messages to discover what specific information users were asking for. To do so, it used pattern matching rules to locate key words, such as the user’s name, which would be stored in variables. If a word was ambiguous, SmarterChild would ask clarifying questions. For instance, if the user wanted information about “Java,” SmarterChild might ask, “Do you mean the coffee, the island, or the programming language?” Once SmarterChild had gathered the information it needed, it would respond with information according to scripts written by the content team.

SmarterChild pin in the CHM collection. CHM catalog number 102751427.

Personality

SmarterChild launched first on AOL Instant Messenger in 2001, and later on Yahoo! Messenger. It wasn’t available on MSN Messenger until after 2004 due to a bug in that platform. On all the services, users would add SmarterChild as a “buddy” in their Buddy List.

Although the initial vision of the chatbot was to deliver information, ActiveBuddy soon discovered that 97% of users (many of them teenagers) were simply chatting with SmarterChild for fun, a category the company classified as “inane chat.” The chatbot’s popularity was boosted by its “profanity handler,” written one weekend by the rock musician employee, who created a database of swearwords and wrote scripts that would respond in a clever way, such as “are all humans so rude?” SmarterChild became known for its snarky responses and persona. At its height, it had over 17 million users and handled 1 billion queries a month, according to Siri investor Shawn Carolan.

GooglyMinotaur was a SmarterChild chatbot created to promote the release of Radiohead’s album Amnesiac. Credit: Robin Bechtel.

ActiveBuddy had a difficult time monetizing SmarterChild. Brand marketing was one attempted use case, promoting products such as Elle Girl magazine, Harry Potter films, and Radiohead album releases. It was also used for customer support bots, like on Comcast’s website. Although this deal was lucrative for ActiveBuddy, Comcast did not allow ActiveBuddy to reveal that Comcast was using SmarterChild, hampering marketing efforts. Although ActiveBuddy (by then renamed Colloquis) was acquired by Microsoft in 2006, its technology was not used by Microsoft’s voice assistant, Cortana, which instead used in-house machine learning.

Legacy

Despite its struggles with a business model, SmarterChild had a clear impact on the voice assistants of the 2000s. In a 2014 Forbes magazine article, venture capitalist Shawn Carolan said that SmarterChild proved there was consumer demand for chatbots. He was influenced to invest in Siri, a spin-off of SRI International that Apple acquired and integrated into the iPhone. Siri too, has a cheeky personality and can engage in witty banter. The legacy of SmarterChild lives on in your iPhone today.

Watch an interview with SmarterChild co-creator Timothy Kay.

Interview with SmarterChild co-creator Timothy Kay, by the author.

Main image: SmarterChild was an Internet chatbot who you friended in your AIM buddy list. You could ask it for information, or chat for fun.

About The Author

Hansen Hsu is a historian and sociologist of technology, and curator of the CHM Software History Center. He works at the intersection of the histories of personal computing, graphical user interfaces, object-oriented programming, and software engineering.

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