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A few days ago, Microsoft officially introduced Microsoft 365 Copilot. This upcoming feature is supposed to help workers who use Office apps a better way to make content. Microsoft hopes Copilot will create Word documents, fill out Excel spreadsheets, summon up PowerPoint presentations, and write Outlook emails for users with AI-driven assistants that humans can then edit and publish.

While the online demos of Copilot look impressive, it did bring up memories of a previous attempt to offer help to Office users: Office Assistant. You may know it better by its most famous avatar: The animated paperclip with beady eyes, Clippy.

It first debuted in Microsoft Office 97, over 25 years ago, with the name Clippit, but it was quickly known by users as Clippy. Many more Office Assistants avatars were also created but none of them reached the level of fame that Clippy received. It was designed by former Microsoft employee Kevan Atteberry. In a 2017 interview with Motherboard, he stated that the origins of Clippy came after the massive failure of another productive app product, Microsoft Bob. He said:

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Oddly enough, a documentary called "Code: Debugging the Gender Gap" would seem to dispute the notion that Clippy was popular with focus groups before its launch. Former Microsoft executive Roz Ho stated."

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In any case, Clippy quickly became a major annoyance for most Office users. The "assistant" would constantly pop up, with phrases like "It looks like you are writing a letter. Would you like help with that?" Many users didn't, or couldn't, shut down these appearances by Clippy. In 2002, with the launch of Office XP, Clippy and all his Office Assistant friends were banished due to poor user feedback.

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However, a funny thing has happened in the last couple of decades. Now that Clippy is no longer appearing while we write a Word document, many people had grown fond of that strange icon. Microsoft has played into this nostalgia for Clippy a number of times over the last several years. Clippy popped up as an April Fool's joke on Office Online in 2014. Later that year, Windows Phone 8.1 with Cortana showed Clippy via an Easter Egg. More recently, Windows 11 included Clippy in its new emojis in 2021.