By Mark Tyson
Publication Date: 2026-04-11 16:27:00
Microsoft’s Clippy was put out to pasture a quarter century ago. This hapless, and some would say ‘irritating,’ productivity assistant would no longer be enabled by default in Office, starting April 11, 2001. Nowadays, it is easy to remember Clippy with some fondness through rose-tinted retro spectacles. But, in its era, Clippy’s repetitive catch-all catch phrases such as “It looks like you’re writing a letter” and “Would you like help with that?” would soon erode any tolerance you might have for cute character-based digital assistants.
Clippy (more properly called Clippit) was a digital assistant introduced with Microsoft Office 97. The plan was to bring a friendly agent to the screen to interface with Office help content, as explained by Wikipedia. Several characters were designed to offer this help, with Clippy (Clipit) as the default choice. Among the alternatives were caricatures of Albert Einstein, William Shakespeare, and Rocky the dog, as well as several…
