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Change is afoot in offices today. And it’s driven by the latest innovation to hit the business world: artificial intelligence (AI). There’s excitement – and anxiety – among employees, managers and business owners as they scramble after AI productivity gains. Meanwhile, AI companies tout ever more miraculous powers for their products.
But there’s a gap between marketing claims and reality. Firms are struggling to work out what this technology can and can’t do for them, often through trial and error. And there’s frustration when tools are not up to the task or tricky to integrate into everyday workflows…
When Microsoft’s AI was compared to… Clippy!
Amid the hype, some voices have been calling out the shortcomings of AI tools. One of these is Salesforce CEO Marc Benioff who, at the end of 2024, savaged the AI tool now built into Microsoft 365: Copilot.
Benioff complained that Copilot “just doesn’t work, and it doesn’t deliver any level of accuracy”. And he didn’t stop there: he went on to compare Copilot to Clippy, the infamously useless virtual assistant that came with Microsoft Office in the nineties and that earned the scorn of generations of users
It should be said that Benioff is far from an impartial observer: Salesforce has launched its own series of AI agents. But it’s nonetheless an interesting comparison that lets us view the present with a bit of perspective, humour and (whisper it) nostalgia.
How will we look back at today’s AI assistants decades from now? Will we see them as we do Clippy today? And did Microsoft’s nineties virtual assistant really meet an ugly end?
Today we’re telling the story of Clippy: how he was born, whom he was designed for and why he’s now being re-assessed in a nostalgic light.
Clippit, the Microsoft Office ‘mascot’ better known as Clippy
Let’s take a step back for a moment: who is Clippy exactly?
Officially named Clippit, he was the default digital assistant built into Microsoft Word from 1996. In the early 2000s, Clippit was disabled in default settings before finally being retired for good in 2007.
Viewed beside (the graphically sterile) Copilot, Clippit – which was quickly rebaptised as the more endearing Clippy – appeared onscreen as a friendly and acrobatic paper clip with bulging eyes and expressive eyebrows. He was supposed to help novice users by showing them what the software could do.
Why everyone hated Clippy
Clippy was omnipresent in the Office suite. And this was a major flaw: he was intrusive and hard to disable. But worst of all, his tips were irrelevant or too simple for most users.
So Clippy became the whipping boy for frustrated users, who got all the more enraged when they realised they couldn’t disable the ineffectual assistant. At the time of Clippy’s launch, Microsoft founder and CEO Bill Gates told the world that with this type of assistant ‘the whole way you interact with the machine will be different’. Yet it turned out that Gates was never completely sold on Clippy, whom he would call ‘the clown’ behind the closed doors.
In 2010, a few years after his retirement, the hated assistant suffered the ignominy of appearing on Time magazine’s list of the 50 worst inventions, alongside Crocs, the Segway and New Coke.
To the relief of many, Clippy was removed from the default Office settings in 2002. When Microsoft broke the news, the company released a little videogame in which users could let of steam by shooting at defenceless Clippys with a hole punch.
In 2007, Clippy disappeared from our computers forever… or at least that’s what we thought!
Who designed Clippy?
‘Who created this bloody paper clip?’ The answer to this question muttered by many a frustrated Windows user in the nineties is Kevan Atteberry. Or at least he’s the man behind Clippy’s graphic design.
Atteberry, who ran a small computer graphics studio and had already done work Microsoft, was hired by the tech giant in 1996 to design a bunch of virtual assistants. In the mid-nineties, many people were encountering personal computers for the first time. With this in mind, Microsoft launched various initiatives to make the experience more ‘human’: some were ill-conceived, like Microsoft Bob, a graphical interface aimed at beginners.
Atteberry created 260 character designs for new virtual assistants, but only 10 of these were included in Office 97.
The most important of these – the one chosen as the default assistant – was, of course, Clippy. Characters who didn’t make the cut included a stapler, a coffee cup and a pencil. Atteberry recalls that it wasn’t hard to come up with the idea of a paper clip: ‘I loved the flexibility, all the things I could do. I loved the fact that I was just using the eyes, because eyes can be so expressive.’ The designs were sent to a team of social psychologists at Stanford University to whittle down the selection. They did this through a series focus groups in which they asked members of the public if they thought characters were trustworthy, likeable and had a sense of humour.
But something clearly went wrong, because Clippy ended up being none of these things. Some have even been suggested that Microsoft misinterpreted Stanford’s analysis. In any case, Clippy became the object of ridicule and exasperation. So much so that, out of shame, Atteberry omitted his creation from his portfolio for years afterwards.
Yet perceptions slowly started to shift thanks to that most powerful of feelings: nostalgia.
Clippy’s comeback
People began to change their mind about Clippy in the mid 2010s. This period saw the emergence of voice assistants like Siri and Alexa who promised to do what the hapless paper clip had tried but failed 20 years earlier: help users instantly get to grips with devices.
In this light, Clippy’s inept efforts now seemed more endearing than maddening. Petitions calling for his resurrection were even launched.
Then, out of the blue, Clippy returned to the Microsoft universe.
On 15 July 2021, the Microsoft Twitter account tweeted a picture of Clippy with the following promise: ‘If this gets 20k likes, we’ll replace the paperclip emoji in Microsoft 365 with Clippy.’
The tweet racked up the 20,000 likes in no time, which is why Clippy can once again be found in the world’s most popular productivity suite. He’s also available in sticker format in Teams and even featured on one of the traditional (and horrendous) Christmas jumpers that Microsoft sells every festive season to raise funds for a good cause.
References to Clippy also come up here and there in pop culture, which seems to have a soft spot for the much-derided virtual assistant. He has appeared in two episodes of The Simpsons and one of Family Guy – at the worst possible moment, naturally. He also features in the videogame Halo 2 Infinite.
Back in the world of AI, there’s now an unofficial app that uses Clippy as an avatar for an assistant powered by ChatGPT. Will the future see retro interfaces given to new AI tools to make them friendlier?
Only time will tell… but until then: long live Clippy!
Do you remember Office’s first virtual assistant? What feelings does he evoke? Nostalgia or annoyance?