Inside the UX lessons, internet lore, and surprising comeback of Clippy

Love him or loathe him, you remember him. Clippy — the googly-eyed paperclip that lived inside Microsoft Word — has become a permanent fixture in internet culture. But how did a productivity tool become the patron saint of annoying-yet-adorable UI? In this episode of Podcast Awesome, we’re digging into the cult of Clippy with behind-the-scenes insights from Clippy's original creator Kevan Atteberry and Microsoft designer Sam Cundall. From meme fame to Microsoft Teams emoji, Clippy's legacy is more layered than you think.

📝 What We Cover in This Episode:

📎 Why Clippy was loved and hated
🧠 The psychology of nostalgic design
🔁 When Microsoft secretly brought Clippy back
🤖 What Clippy might teach us about the future of AI assistants
✍️ thoughts on reviving legacy designs the right way

⏱️ Timestamps:
00:00 – Welcome to the Cult of Clippy
02:00 – The origin story: from helpful to hated
04:30 – Nostalgia and annoyance: why we love to hate him
06:00 – Microsoft’s secret Clippy emoji comeback
08:00 – What makes emoji design "work"?
10:00 – Fun at work: why weirdness builds culture
14:00 – The creator's take: Kevan Atteberry on designing Clippy
20:00 – From embarrassment to pride: Clippy's redemption arc
24:00 – Clippy vs. Siri: The rise of personality-driven UI
26:00 – Final thoughts: where personality fits in UX

🔗 Links & Resources:

Sam Kundal on LinkedIn
Kevan Atteberry's books
How to add a paperclip emoji to your UI
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🎥 Podcast Awesome on YouTube
🎶 The Font Awesome Theme Song – Composed by Ronnie Martin
🎸 Music Interstitials by Zach Malm
🎬 Produced and edited by Matt Johnson with some extra help from Isaac Chase

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Clippy Cult: The Paperclip That Wouldn’t Quit