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Before AI agents, before chatbots and before Copilot, there were once bizarre animated creatures that would pop up in Word or Excel to offer help.
They were the Microsoft Office Assistants.
You might remember the most famous of all: Clippy, the much-hated anthropomorphised paper clip whose seemingly helpful hints – which almost always turned out to be useless – were supposed to make Microsoft technology easier to use. Named one of the 50 worst inventions of all time, we’ve already dedicated an entertaining article to the little guy on this blog.
But Clippy wasn’t the only Microsoft assistant: his creator, American illustrator Kevan Atteberry, actually designed some 260 characters altogether. Only a dozen or so were initially selected by the firm, but over time, more eccentric helpers were added to the team of assistants.
Today we’re going to tell the story of Clippy’s brothers and sisters, the forgotten Microsoft Office Assistants.
Microsoft Office Assistants from the turn of the millennium
Let’s start with a bit of context for those of you who weren’t around at the time. The first virtual assistants arrived in 1995 with what was a famous flop for Bill Gates and co.: Microsoft Bob, a graphic interface designed to help those new to personal computers.
Then came Clippy, along with a gaggle of other assistants who lent a (not so) helping hand in Office 97, 98, 2000 and 2001. Office XP, released in 2001, spelt the beginning of the end for these characters, who from then on were turned off by default. They disappeared completely in 2007.
So in the late nineties and early noughties, a motley crew of weird but not so wonderful characters would pop up on the screens of unfortunate Office users – Clippy being the best known: there were cats, dogs, robots and punctuation marks, Einstein, Shakespeare and Merlin the wizard, as well as other nonsensical beings that could pass for Italian brainrot characters. [Speaking of which, check out our blog post on the origins of this phenomenon].
Microsoft Office Assistants didn’t just give tips – they kept users company, too. A series of amusing animations showed them getting up to all sorts. Looking back, they now seem almost endearingly.
A gallery of Microsoft Office Assistants strutting their stuff.
The forgotten Microsoft Office Assistants
So who were the other Microsoft Office Assistants? It’s time to meet Clippy’s colleagues.
Dot, the smiley red ball.
Hoverbot, an odd, egg-shaped robot with a strip of red lights for eyes. According to its description: ‘Cruising at an altitude of 3 to 6 inches, Hoverbot can help you get more out of Office.’ Whether that was really the case is another question.
Hoverbot in Office 97. Image: agentpedia.tmafe.com
PowerPup, a cute dog with a superhero cape. Despite his supposed superpowers, he was little help to users of the software suite!
The most on brand and least interesting of the assistants was the Office Logo – the unimaginative name alone says it all. It was an animated version of the old Office logo, which was four coloured puzzle pieces put together to form a square.
Genius is a caricature of that archetypical brainiac: Albert Einstein. Sadly, he met an unhappy end. For reasons unknown, he was removed as a default option from Office XP, although he could still be downloaded as an add-on.
Sticking with celebrities, we give you… Will. This assistant was a tribute to William Shakespeare. But it wasn’t long before he too shuffled off this mortal coil: he was ditched in Office 2000.
Scribble was a cat that was part collage, part cubist painting. Here’s her bio: ‘This artful cat is made of paper, but there’s nothing two-dimensional about her knowledge of Office.’ From Windows 2000 onwards, she was replaced by a less abstract but more cutesy feline called Links.
Users who needed help with Office could even call on Mother Nature! While she lent a hand, this virtual assistant might metamorphose into a dove, sunflower or butterfly.
Merlin was one of the last assistants to be added to Office before they all got the chop. Fashioned after the mythical magician, he arrived with Office XP in 2001. Alas, he failed to enchant Windows users!
But perhaps the most absurd assistant of them all was F1. This robot with legs doubling as arms was named after the F1 key, which opens the help window in Office applications to this day. But what’s with its bizarre shape? Are those things on its hands/feet mice or what? And why does it sometimes pretend to be a dog?
The Office Assistants for the Mac
To say there’s no love lost between Microsoft and Apple is an understatement. Both brands inspire loyal followings, and for years fans of each system have been locked in an endless argument about which is best, ever eager to share personal experiences when making their case.
So where did Clippy creator Kevan Atteberry’s allegiance lie? In this interview, the designer admitted with a proud grin that he produced the final design for the assistant on his… Macintosh!
Despite this fierce rivalry, in 1998 Microsoft began offering a version of Office for the Mac: Office 98. This meant that Apple users, who until that point had (perhaps fortunately) lived without virtual assistants, got to meet digital helpers designed especially for them.
Earl The Cat – a mischievous blue feline clearly inspired by Tom of Tom and Jerry fame – was probably the most endearing of these. He could actually be downloaded in Office 97, but was only made available by default in the Apple version.
Then there was buttoned-up butler Bosgrove and Max, a Macintosh Plus computer that had sprouted a pair of legs.
And finally we had Rocky. A hit with kids, this cheery tail-wagging puppy wasn’t exclusive to the Macintosh, but got the nod as the default assistant for Office 98 ahead of Clippy.
Nineties Office Assistants for Asian audiences
To wrap up this nineties nostalgia fest, here are some Office Assistants that you’ve probably never seen or heard of: those created for Asian editions of the productivity suite.
Among them were Saeko Sensei, a teacher drawn in a manga style, and a character called Monkey King.
The latter is a simian based on the eponymous protagonist – known as Sun Wukong in Chinese and Son Goku in Japanese – from a classic of Chinese literature, Journey to the West. Fun fact: this monkey with magical powers also inspired the manga Dragon Ball.
And we can’t forget Kairu, the dolphin.
In the Japanese edition of Office, it wasn’t Clippy constantly hassling you with unsolicited offers for help, but this cetacean creation.
Did you enjoy this rogues gallery of turn-of-the-millennium Office Assistants? Did you remember any? And did you prefer these characters to today’s faceless chatbots? Share your thoughts!
For images and further information on Microsoft’s mascots: agentpedia.tmafe.com