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Bob, 1995 — Chock-full of metaphors (analog clocks, wall calendars, Rolodexes), Bob featured a guide (usually Rover the Dog) that exclaimed, “Looky! Camper!” and explained everything. Childish, convoluted, ridiculous, despised.

Office Assistant, 1997 — Clippy ("one of the most annoying characters in history," said its creator) tapped at the screen, tried to guess what you were working on, and always smiled, even if you were writing about Grandma’s funeral.

Blue Screen Of Death, 1998 — Indelibly associated with unsaved projects lost forever, the infamous crash screen became a metaphor for Microsoft’s unreliability. Windows 8 will replace it with a large, sad emoticon.

Mira Smart Display, 2002 — The Mira display let users access their PC wirelessly from 100 feet away. Though convenient (you can work from the couch!), its bulk and $1,000 price tag left it dead in the water.
Jeff Christensen/AFP/Getty Images

Windows Mobile, 2003 — Yes, you could edit a spreadsheet on the bus, but all the devices using it had small, low-res, stylus-dependent screens. Totally crushed by smartphones from RIM, Apple, and Google, Mobile was retired in 2010.

Zune, 2006 — Microsoft’s years-late response to the iPod, the Zune was buggy, heavy, and usable only with Windows PCs. Microsoft channeled the best features, such as sleek typography-based navigation, to the Windows Phone.

Windows Vista, 2007 — Both dumbed down and complicated, Vista had cryptic icons and required multiple steps for simple actions like shutdown. It was such a mess people believed an April Fools’ joke that Bob was hidden inside.

“Would You Like Help?” Microsoft Design Flops Through The Ages

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Infographic of the Day

Infographic of the Day: Infographic: How To Tell The Difference Between 66 Varieties Of Cheese

Innovation by Design

The Amazing Judges For Our 2013 Innovation By Design Awards

From the Editor

Thanks for stopping by Fast Company’s Co.Design. If you’ve been a reader for some time, you’ll notice that we’ve just unveiled a brand-new redesign. You can read about the thought process behind it here. Our content, of course, will be the same: Our focus is on highlighting the world’s best examples of design and innovation, working in concert.

We started this site with a few simple premises in mind. First, design is a window onto the world at large, and the culture we live in.

Continued