Benjamin Cassidy, in a really fun article looking at the life — and death — of Clippy:
Clippy was born on a Mac. When Kevan Atteberry was hired to design characters for Microsoft Bob and Office 97, he’d shuttle between the company’s leafy grounds and his Bellevue studio space, where a desktop made by a certain rival awaited. Animation required using Microsoft’s proprietary software, but before hustling files over to HQ, he could tinker in his second-floor walk-up with tons of light and a landlord who never raised the rent. It was here he picked up a Ticonderoga two-and-five-tenths pencil and started outlining an infamous paperclip. Digitizing it just meant closing the blinds and booting up the Macintosh he preferred to his employer’s PCs.
“This is my original Clippy,” Atteberry says one recent morning, pulling up an image on an iMac.