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 ...

Software engineer ‪Felix Rieseberg has resurrected the Clippy with Artificial Intelligence capability. It retains the retro look of the paperclip with expressive cartoonish rounder eyes and eyebrows.

If you were using Microsoft Word in the late ‘90s, you probably remember Clippy, the anthropomorphic paperclip who popped up from time to time in order to offer tips on how to better use 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 ...

Kevan Atteberry, the man behind Microsoft Word's virtual assistant, had no idea how big Clippy would be today, especially after the growing disdain for the anthropomorphic paperclip throughout the ...