Top 10 Microsoft Moments

One of the more controversial ventures in Microsoft's history — both because of its spectacular failure to take off in the market and its prescient foreshadowing of user interfaces to come — Bob was unfortunately ahead of its time. Released in March 1995, with Melinda Gates, Bill's newly wedded wife, as lead marketing manager, it differed greatly from Windows' menu-based, text-heavy interface.

Instead, Bob presented a desktop screen as an image of a room with a desk, a bookshelf, a fireplace and other items. The various items in the room — a Rolodex, calendar, checkbook — started the appropriate programs. "Bob was the first software that was really task-oriented as opposed to program-oriented," Clifford Nass, a Stanford professor who helped develop Bob, told the Pittsburgh Post-Gazette in 1999. It was a precursor to the programs today that learn user habits, making more popular applications more prominent. In addition to poor sales, Bob was incapable of competing with Microsoft's newest wonder, Windows 95, and was discontinued after a year.