Microsoft’s Clippy was put out to pasture a quarter century ago. This hapless, and some would say ‘irritating,’ productivity assistant would no longer be enabled by default in Office, starting April 11, 2001. Nowadays, it is easy to remember Clippy with some fondness through rose-tinted retro spectacles. But, in its era, Clippy’s repetitive catch-all catch phrases such as “It looks like you’re writing a letter” and “Would you like help with that?” would soon erode any tolerance you might have for cute character-based digital assistants.

Clippy (more properly called Clippit) was a digital assistant introduced with Microsoft Office 97. The plan was to bring a friendly agent to the screen to interface with Office help content, as explained by Wikipedia. Several characters were designed to offer this help, with Clippy (Clipit) as the default choice. Among the alternatives were caricatures of Albert Einstein, William Shakespeare, and Rocky the dog, as well as several animated inanimate objects (like the unpopular paperclip).

Some esteemed figures in the computer industry think that the introduction of Clippy might have been a "tragic misunderstanding" of research conducted at Stanford University on breaking barriers in human-machine interaction. Indeed, there must have been something seriously wrong with a ‘helpful’ project like this for it to attract so much ire and ridicule among users and tech commentators.

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Rose-tinted retro spectacles

Clippy’s infamy has been sealed with its place in Time magazine’s 50 worst inventions. However, the mists of time have taken the edge off the pain of working with such a useless assistant, as it is now often viewed as being part of an amusing, heart-warming era in computing.

Microsoft has played on this softening of public opinion, or even nostalgia, for Clippy in several marketing campaigns since the animated paperclip and his friends were discarded. Most recently, it resurrected Clippy as an Emoji in Microsoft 365 – after overwhelming popular demand.

Last year, as the wave of new AI assistants began to grate on the public nerves, we also observed some fondness for Clippy being rekindled in a project by software engineer Felix Rieseberg – a locally hosted, LLM-based, AI-enhanced Clippy, complete with Office 97-era-appropriate UI.

Despite the sting of Clippy's clear failure, Microsoft keeps coming back to digital assistants as the future of computing. We had Windows Cortana foisted upon us from 2014 to 2023.

Now we have Copilot everywhere, in every corner of our Windows 11 PCs and Microsoft apps. A recent count indicates that there are at least 80, and probably over 100 Copilot apps…

As optimists, we hope Copilot will be reined in, as far as Windows goes, thanks to Microsoft’s latest stated initiative to focus on OS performance, reliability, and RAM usage. This telegraphed change is also supposed to lead to fewer Copilot interactions.

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Mark Tyson is a news editor at Tom's Hardware. He enjoys covering the full breadth of PC tech; from business and semiconductor design to products approaching the edge of reason.