It began with Clippy

“It looks like you’re doing something that requires me to pop up on the screen and distract you from the task at hand.” That was the basic gist of Microsoft’s Clippy, often referred to as the world’s most hated virtual assistant (ouch). I wouldn’t go as far as to say I hated Clippy, though it definitely had a habit of popping up at the most unnecessary time. Microsoft introduced Clippy in 1996 to try and help users with its new at-the-time Office software. But the minute you’d start typing out something, the animated little paper clip would pop up and ask how it could help, assuming you needed aid starting your draft.
Microsoft eventually sunsetted Clippy within its Office suite in 2007. Clippy has since been memorialized in the form of various fan-made Chrome extensions. Microsoft even made an official Clippy emoji in Windows 11.