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.

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.

Co.Design

"Would You Like Help?" Microsoft Design Flops Through The Ages

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