It was January 1995. Microsoft was riding high. Windows 3.1 had sold well. The interim replacement, Windows 3.11, was selling well. The industry was abuzz for the upcoming Windows 95, expected sometime later in the year. Microsoft was in a golden era, a time when nothing could go wrong for them. And then they released Microsoft Bob. They should have named it Microsoft Bomb, because it bombed. But if you take one letter out of Bomb, you get Bob. So they almost got it right.
What was Microsoft Bob?
Microsoft Bob was a replacement user interface for Windows for novice computer users, replacing the conventional Program Manager or Explorer interface with something friendlier. Announced in early January 1995 and released March 11, 1995, Microsoft quietly discontinued it in 1996, just about a year later.
Microsoft Bob presented screens showing a house, with rooms that the user could visit containing familiar objects corresponding to computer applications, such as a desk with pen and paper and a checkbook. Clicking on the pen and paper would open the system’s word processor. Cartoon characters like a cartoon dog named Rover provided guidance using speech balloons.
The media criticized Microsoft Bob and its users didn’t like it much either. But elements of it appeared in later, more successful products, such as Office 97’s virtual assistants and the Windows XP search companion.
Microsoft Bob includes various productivity applications like a finance application and a word processor.
Bob had the ability to install new applications, but because the product failed, Microsoft only ever released one add-on application package, Microsoft Great Greetings.
What went wrong
Although a Consumer Electronics Show demonstration was met with generally positive reactions, reviewers generally derided the software, and Microsoft Bob became one of Microsoft’s more visible product failures.
According to PC Data, Microsoft Bob only sold 58,000 copies—far short of Microsoft’s estimate that it would sell millions as had Microsoft Works and Encarta. Despite being discontinued just one year after launch, Microsoft Bob continued to be sharply criticized in reviews and popular media.
Part of the problem was that Bob was slow and resource-hungry unless you had a very fast machine. But novices weren’t likely to buy the most expensive PC on the market. In 2017, Melinda Gates, Bill Gates’ ex-wife and the product’s marketing manager, acknowledged that the software “needed a more powerful computer than most people had back then.” Modern analysis backs this up. When running Bob on a Pentium-class machine, the software becomes more tolerable. But in January 1995, the mainstream PC still typically packed a 486.
PC World magazine ranked Microsoft Bob #7 on its list of the 25 worst tech products of all time. CNET ranked it the number-one worst product of the decade. Time magazine listed it among the 50 worst inventions, calling Bob “overly cutesy” and an “operating system designed around Clippy.”
But we can also question whether it was necessary. Commodore attempted a similar UI way back in the summer of 1983 called Magic Desk. It behaved very much like Microsoft Bob, except without trying to be overly cute. It also failed, largely because it was too simplistic.
Microsoft Bob’s legacy
Microsoft included an encrypted copy of Bob on Windows XP installation CDs to waste space to discourage piracy. Consuming an additional 30 megabytes on the disc in the era of dial-up internet access might deter users with 56 kbit/s modems from attempting to download the software illegally. It sounds like an urban legend but former Microsoft engineers have confirmed its presence on the CD.
Microsoft graphic designer Vincent Connare designed the typeface Comic Sans when he noticed that Rover’s speech was displayed in Times New Roman, which seemed inappropriate for a cartoon dog. Although Connare’s font did not appear in the final release of Microsoft Bob because its characters did not fit within any of the typographical grids, it later found its way into Windows 95 and future Windows releases. It’s somehow appropriate that the most derided font in Windows was an outtake from Microsoft Bob.
David Farquhar is a computer security professional, entrepreneur, and author. He has written professionally about computers since 1991, so he was writing about retro computers when they were still new. He has been working in IT professionally since 1994 and has specialized in vulnerability management since 2013. He holds Security+ and CISSP certifications. Today he blogs five times a week, mostly about retro computers and retro gaming covering the time period from 1975 to 2000.
The criticism of Comic Sans is misplaced. It’s a perfectly fine typeface when used for its intended purpose, which is to emulate hand drawn lettering of comics as its name implies. I understand that many dyslexic people find it easy to read.
The people that should get criticized are the ones who use it in inappropriate ways. Comic Sans was never intended to be a body typefaces for most purposes. Nor was it intended to be a display typeface for general purpose use, though it’s fine if it’s associated with things like comics.
Overuse and misuse is a common problem with fonts. I absolutely hated Helvetica in the 90s. Not because it’s a bad font, it’s one of the greatest fonts of all time. But because 99% of documents used it, I got sick of looking at it. Now that you don’t see it nearly as often it looks like a classic font again.
And in todays world there is comic code as a monospace option for many coders who are willing to pay for a font.
I have, a couple times in my former career as an interaction designer, had clueless bosses press me to implement exactly this type of UI, as though they came up with this “great idea”. Both times, I managed to wiggle out of it, but I made no friends in the process.
Sure wish I could invest in Stupid. It’s a growth market.