The OG AI Assistant: Celebrating Clippy on National Paperclip Day

A Nostalgic Ode for National Paperclip Day 📎

If you ever opened a Microsoft Word document in the late 90s or early 2000s, chances are you were greeted by a wide-eyed, wiggly paperclip who just wanted to help. And by “help,” we mean pop up uninvited, bounce around your screen like he drank too much coffee, and offer to help you write a letter you never asked to write.

But in his own chaotic way, Clippy (full name: Clippit) was ahead of his time. He was basically the proto-AI assistant; offering (sometimes useful) suggestions, reacting to what you were typing, and giving your doc that oddly sentient energy.

Clippy made his debut in Microsoft Office 97 and quickly became either:

1. Your quirky productivity pal.

2. Or the animated embodiment of “No thanks, I got it.”

For years, he danced, blinked, and blurted out help tips that were occasionally relevant, often unnecessary, and somehow... comforting? Annoying? It’s hard to say. Clippy lived in a strange limbo between nostalgia and nuisance — like a well-meaning coworker who won’t stop hovering while you’re trying to finish a project.

Despite the backlash (and eventual retirement in the early 2000s), Clippy’s legacy endures. He walked so Siri, Alexa, and ChatGPT could run, or at least roll in with a little less bounce.

And for creatives, he was just the beginning. From auto-alignment tools in early design software to smart layout suggestions in Adobe and Canva today, AI assistants have been quietly shaping the way we work since the 90s. What started as a googly-eyed clip-on guide has evolved into sophisticated creative tool — helping designers streamline workflows, offer new tool capabilities and even generate content for initial ideations.

Turns out, Clippy might’ve been onto something after all.

So this National Paperclip Day (May 29), we salute the most unforgettable, mildly unhinged virtual assistant of our time. 🫡

Thanks for the memories, Clippy. And for asking — over and over — if we were writing a letter.