Information Technology

From a Talking Paperclip to a Purple Gorilla

The Good, the Bad, and the Ugly of Early Digital Assistants

Ryan Michael Fabayos
6 min readOct 25, 2024
Image created using Canva Pro

Imagine a society in which you always have access to a personal assistant, seven days a week. Finding information on the internet or on your phone doesn’t have to be difficult. You can ask any of your digital assistants — Alexa, Siri, Cortana, Google Now, or Bixby — for help, somewhat a lifesaver.

Nowadays, we take these sophisticated AI-powered helpers for granted. They can do a wide range of tasks, including setting reminders and managing smart home appliances. But this was not always the case. In the early days of personal computing, digital companions were novel and often more of a distraction than a benefit.

Let’s take a trip down memory lane and revisit these early digital assistants. As we explore their limitations and quirks, we’ll appreciate the incredible advancements that have been made in the field of artificial intelligence.

BonziBuddy: The Purple Gorilla That Wasn’t So Friendly

BonziBuddy, a purple gorilla who became well-known in the late 1990s, was more than just a strange cartoon character. It was a classic example of the early days of digital assistants and a warning about the dangers of unchecked software development.

Originally developed by Bonzi Software, BonziBuddy was intended to help users with a variety of tasks, including playing games, reading emails, and making appointments. It was a popular choice among computer users, particularly kids, because to its interactive features and welcoming manner.

But underneath its endearing façade, BonziBuddy had a sinister secret. User data, including as browsing history, keystrokes, and personal information, was being surreptitiously collected by the software. Malicious software was then installed on users’ PCs and targeted with customized ads using this data.

To deceive individuals, the creators of BonziBuddy employed a variety of tactics. Using false claims that viruses were on their systems, they would bombard customers with misleading pop-up ads (adwares). Afterward, these commercials would encourage users to acquire additional Bonzi software, which often contained even more malware.

Despite its malicious character, BonziBuddy remained popular for a lot of years. Its success was influenced by several factors, including the fact that it was free, the novelty of having a virtual assistant, and the lack of awareness at the time regarding internet security threats.

However, BonziBuddy’s popularity started to wane as individuals realized how dangerous online scams can be. A class-action lawsuit against Bonzi Software was filed in 2004 due to BonziBuddy’s dishonest business tactics. The business was found to have collected children’s personal information without parental authorization, in violation of the Children’s Online Privacy Protection Act (COPPA). Consequently, Bonzi Software had to pay a large fine and was shut down.

The legacy of BonziBuddy serves as a warning about the significance of internet security and the necessity of exercising caution when downloading software from unidentified sources. It also emphasizes the significance of ethical issues in the production of digital products and the possible risks associated with unregulated software development.

Microsoft Bob: The Quirky Companion That Time Forgot

Does the computer software named “Bob” seem familiar to you? Microsoft Bob is the king of tech flops — or, perhaps more appropriately, the king for a brief period of time (during the 90s). Bob, a vibrant and whimsical desktop environment, was released in 1995 as a bold attempt to make computers more accessible to novice users. The purpose of the application was to replace the standard Windows 3.1 interface with one that is more visually appealing and intuitive.

Instead, users explored a virtual house to engage with Bob rather than going through folders and data. Each room in the house served a distinct purpose, such as the bedroom for private settings, the living room for entertainment, and the study for work.

To guide users through this virtual world, Bob introduced a friendly cartoon dog named Rover. Rover would provide helpful tips and suggestions, making the experience more approachable for those who were new to computers.

Microsoft Bob failed commercially in spite of its creative approach. Its demise was caused by several factors:

  • Too Adorable, Too Complicated: Many users, both new and seasoned, found the adorable user interface (UI) to be juvenile and perplexing.
  • Performance Issues: Bob was a resource hog, slowing down even the beefiest computers of the era.
  • Misunderstood Market: While Bob aimed to simplify computing, it ended up alienating both novice and experienced users.

However, Bob wasn’t all bad. Its “real-world” interface foreshadowed the future of Augmented Reality (AR), where technology seamlessly blends with our physical environment. Additionally, Bob’s helpful canine companion, Rover, paved the way for Microsoft’s infamous Clippy the paperclip (up next).

Despite its commercial failure, Bob remains a fascinating example of early software design and a reminder of the importance of user experience (UX). It highlights the challenges of creating intuitive and accessible software, even for novice users.

Clippy: The Paperclip That Wasn’t So Helpful

Remember that annoying paperclip that used to pop up on your computer screen whenever you opened Microsoft Word? That was Clippy, Microsoft’s effort at creating a ‘helpful’ virtual assistant for Microsoft Office, or is it?

Clippy, was a prime example of early virtual assistants gone bad. Introduced in 1997 as part of Microsoft Office 97, it was designed to offer assistance and guidance to users who were new to computers.

But Clippy’s excessively enthusiastic and frequently irrelevant ideas soon turned it into a joke and a representation of Microsoft’s late 1990s mistakes. The cartoonish and very simple design of the paperclip gave it a juvenile and amateurish appearance. Furthermore, Clippy was more of a distraction than a help due to its intrusive nature and lack of intelligence.

The legacy of Clippy is extensive despite its flaws. Having made appearances in TV shows, video games, and memes, the character has become a cultural icon. Clippy’s story emphasizes the importance of developing technology that is both discrete and helpful.

Despite Clippy being a mistake, virtual assistants have come a long way since the 1990s. Advanced AI-powered assistants are available today and can perform a wide range of tasks. However, their ability to understand user intent and provide truly helpful support is still lacking.

Conclusion

As we bid farewell to Clippy, BonziBuddy, and Microsoft Bob (and Rover too), let us remember their contributions to the world of personal computing. These quirky little characters helped to pioneer the concept of digital assistants, paving the way for the sophisticated AI-powered companions we have today.

Their techniques were often incorrect, but their goals were always excellent. These early digital assistants showed us how technology can enhance our lives in many ways by making computers more accessible and approachable to a wider range of people.

Thus, the next time you interact with your digital assistant, take a moment to reflect about the journey it has taken to arrive at its current condition. Digital assistants have made incredible strides, evolving from the unwieldy and often ineffectual companions of the past to the perceptive and intelligent assistants of today.

Who knows what the future will bring? Digital assistants that can actually comprehend our needs and feelings might become available to us in the future, offering us individualized support and company that beyond our current capabilities.

Until then, let’s continue to explore the exciting world of digital assistants and see where this incredible technology will take us next. ✦

I hope you enjoyed reading this article. After more than a year of hiatus, I’m back here at Medium and did a new post just days ago, and hopefully it will be a brand new start. Again, I sincerely appreciate all your responses, and I need those to help me improve my writing. You can subscribe to my mailing list for my upcoming posts and buy me a coffee.

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© 2024 Ryan Michael Fabayos

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