Clippy appears in a Windows 95 pop-up saying, 'I see you’re trying to focus on something without interruption. Can I help?' in retro pixelated style.

The Rise and Fall of Clippy: From Microsoft's Bold Vision to Internet Legend

I still remember the first time Clippy popped up on my screen. There I was in early 1997, a few years into my IT career, wearing my cheap suit and gaudy tie as young office techies had to do back then, writing documentation for some consulting project. In the middle of all this arbitrary workplace formality, a cartoon paperclip suddenly materialized on my screen like some kind of malware attack, complete with those unmistakable eyebrows, asking if I needed help writing a letter. There was nothing like it at the time—it was simultaneously curious and deeply unsettling. My immediate reaction? “Get lost, paperclip.” ...