In the 1990s, Microsoft created a virtual assistant in Microsoft Office that users found annoying — so it was swiftly retired. For Seattle Met, Benjamin Cassidy recounts the history of an unloved and doomed office assistant that has lived on in pop and nerd culture.

These days, an annoying Word creature might seem eminently tolerable compared to the ghouls on Twitter. Now that Alexa’s in our bedroom and Siri’s in our hand, Clippy’s a throwback to what seems like a more benign digital age.

Cheri has been an editor at Longreads since 2014. She's currently based in the San Francisco Bay Area.