The Tragic Life of Clippy

It looks like you’re reading an article, would you like help with that?

Sam Tolman
2 min readJun 8, 2021

According to Wikipedia, Clippy, also known as Office Assistant, is —

The Office Assistant is a discontinued intelligent user interface for Microsoft Office that assisted users by way of an interactive animated character which interfaced with the Office help content.

So how did we go from Clippy, or Clippit, to Microsoft using Clippy’s tomb to promote their 2010 new OS update? Well, answer’s pretty clear — the experience was almost opposite of what it was intended to be.

A patronizing paper clip

When one hears the word “assistant”, characteristics of someone who is loyal, focused and other-centered — in this case, Clippy was that, to himself and whatever quest for chaos he was onto.

In a time where computer knowledge was not widely available and software UX/UI hadn’t found it’s footing, Clippy who’s often patronizing tone would deter, rather than invite the user to use his services. The famous line, “Looks like you’re writing a letter, would you like help with that?” made a user feel stupid before even finishing the address line.

Creepy clip

Clippy wasn’t exactly a friendly looking clip, example being —

no thanks

Clippy’s eyelids were often half way open, either looking like Clippy was giving you some side-eyed stare or stoned out of his mind. Either way, the character evoked emotions of un-assuredness before comfort.

A clear disconnect

So what the hell happened? There was a clear disconnect between the product and the consumer — a lack of research, but not from an educational perspective. Clippy, or the Office Assistant, was developed by two Stanford professors, from their research at, well, Stanford. The problem was — that’s all the research that was used to develop it. No UX/UI testing, talking to consumers. A product put out by a small group of people, failing to make a connection with its target audience.

Today, Clippy’s legacy lives on as the definition of annoyance, a legend Microsoft seemingly cannot get away from.

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Sam Tolman
Sam Tolman

Written by Sam Tolman

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