The 50 Worst Inventions

Imagine a whole operating system designed around Clippy, and you get the crux of Microsoft Bob. Designed to be an easier interface for Windows 95 users, Bob envisioned your computer as his house — with you as a guest. Ever so accommodating, he'd even supply cartoon sidekicks to guide you through simple tasks. The software was expensive and overly cutesy, and it failed to compete with Apple's Macintosh, the user-friendly standard. And though Bob is long gone, he left one enduring blight on the Web: Comic Sans, perhaps the worst font of all time, was created exclusively for Bob.