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…

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