Chutzpah: Tech's Biggest Broken Promises

By Cliff Edwards - 2012-03-05T20:01:26Z

Courtesy Microsoft

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Microsoft BOB (1995)

Software comes and goes, but BOB has left a lasting impression as one of the worst tech products of all time. Introduced with the O featuring a yellow smiley face wearing nerdy glasses, BOB was designed to replace the desktop of Windows 3.1 and 95 with an interface designed mainly for novice users. Company engineers optimistically labeled the project "Utopia."

Cartoon assistants and virtual pathways to applications caused more confusion than clarity. Microsoft Chief Executive Officer Steve Ballmer later called it a situation "where we decided that we have not succeeded and let's stop."