Microsoft Clippy, the animated cartoon paperclip everyone loved to hate, is seeing a resurgence in popularity. Clippy is now being recognized as the trailblazer he was. When Chloe Condon, a newly ...

Halo Infinite season 2 may be titled Lone Wolves, but Spartans will never have to go it alone in battle, thanks to the arrival of Clippy, the cartoon paperclip virtual assistant from the Microsoft ...

It’s 1997. You’re hooked up to a modem and are typing away on a Microsoft document when an animated paperclip pops onto the screen. “It looks like you’re writing a letter. Would you like help?” was a ...

Software devs love peppering their releases with a few well-placed Easter eggs, and voice-based virtual assistants on smartphones have been no stranger to this trend: Siri can be goaded into telling ...

Microsoft Hopes Mico Succeeds Where Clippy Failed as Tech Companies Warily Imbue AI With Personality Clippy, the animated paper clip that annoyed Microsoft Office users nearly three decades ago, might ...

It’s human nature to hate things that remind us of how dumb we used to be; Like teenagers who can’t stand their baby pictures, we prefer to ignore the proof of our humble beginnings. The same goes for ...

Of all the peculiar ideas that Microsoft has pursued over its almost 34 years in business, I can’t think of many that are more inexplicable than its long-standing interest in using animated characters ...

Editor’s Note: A version of this story appeared in CNN Business’ Nightcap newsletter. To get it in your inbox, sign up for free, here. This week, Microsoft confirmed it’s planning to invest billions ...