Seemingly aimed at a six year-old with a geography degree and finances to manage, Microsoft Bob represents possibly the most bizarre software flop of all time. Released in 1995, Bob was a graphical shell that ran on top of Windows 3.1 and Windows 95, and was designed to make computers more accessible for people who simply didn't understand Microsoft computers. The main result was in fact the revelation that Microsoft simply didn't understand people.

The Basics

The main graphical user interface at the time was that of Windows 3.1 - a series of drab windows containing various icons, with little assistance for those confused by the brave new world of computing. In order to make using your computer friendlier, Bob turned it into a house, complete with rooms, doors and pointless pot plants. Upon starting, Bob would display the door to your new virtual home, which like most homes had no real security whatsoever once you were through the front door. The first room you would arrive in was the Public Family Room, commonly known to most normal people as a lounge. Although a variety of customised rooms were available, each room basically acted as a desktop, with items scattered around the room acting as shortcuts to different programs. In case things got too simple, each room could also contain as many useless items as the user wanted, including the pot plants, fires, and chairs you might find in any home. Some rooms could be designated as private, but this was about as useful as closing your bedroom door - anyone could get in if they really wanted to.

Personal Guides

Unfortunately, Bob came with a series of personal guides, one of which would always be sitting in the corner of your screen reminding you how to breathe and commenting on the dangers of swallowing your tongue. The default assistant was Rover, a Golden Retriever who claimed to hail from Redmond, WA, but now lives in the Windows XP search facility. Users could exchange Rover for any one of the 'scrumptious gang', which included a guitar-playing rat, a French cat, a dragon addicted to caffeine, a stuffed blue rabbit, and a parrot who looked terminally constipated.

While each guide came with a different 'personality'¹, their main job was to tell you how to do almost everything and it would seem that there was a general assumption that someone else had been there to help you switch on the computer in the first place. Even better, the guides all had verbal diarrhoea to the point that they would keep talking even if you weren't trying to do anything, and would happily ramble on about the most boring aspects of their lives and the lives of the other guides.

After They Were Famous

Having appeared in Microsoft Bob, a handful of the guides moved on to pastures new, using the skills they had learnt to irritate a whole new generation of PC users. You may have heard of The Dot and Will, both of whom went on to appear as side attractions in Microsoft Word up until the release of Windows Vista in 2007, when both they and the famous paperclip, Clippit, were finally consigned to the scrapheap. Meanwhile, Rover continued to irritate by appearing in the Windows XP search facility, although thankfully there was an option to turn him off.

Applications, Bob-Style

Bob included several applications which Microsoft decided to strip down to the bare minimum while moving most of the features to the personal guide's speech bubble. A couple of applications even came with their own special personal guides, some of whom seemed to get quite upset if you tried to close their program and get on with your life. Programs included a finance manager and chequebook in which users were 'interviewed' about their finances by a book with bad glasses, a text editor which had almost no features, a geography quiz which came complete with a purple elephant called Hank, and finally a 'financial guide' and a 'household manager'. The latter two each consisted of reams of advice on how to live your life, and came with the rather bizarre disclaimer: Textual information may not be accurate or complete and is not intended to replace consultation with a professional.

Could It Possibly Be More Irritating?

For those readers who have never experienced Microsoft Bob, here are some of the 'highlights':

• The Bob Magazine, a paper supplement to the program, making inroads to being even more patronising than the personal guides.

• The guides telling you to click on a program to start it even when you've proved a thousand times that you're capable of doing so.

• Rover adding 'Bow-wow', 'Rrruff' or 'Woof woof' to his sentences for no reason.

• Hopper, the stuffed blue bunny, looking like he's going to murder you in your sleep.

• The Speaker, yet another guide, listing his favourite food as AC/DC.

• The chequebook personal assistant telling you to 'stick with it' when you try to leave his 'interview'.

• The 'Cancel' button randomly cycling through 'Never Mind', 'Forget It' and 'Nuh'.

• The personal guides using your name before every single thing they say to you.

• The personal guides patronising you with comments such as 'Here we go!', 'Good job so far!' and 'It's a room just for you!'.

Why Did It Fail?

While it may have seemed like a good idea at the time, Microsoft Bob was more or less doomed from the beginning. For starters, its system requirements were too great for many of the computers in use at the time, and the program's cost was too great considering its limited functionality. Also, the interface was a little too 'cutesy' for users who were used to the drab Windows 3.1 interface, and pretty much failed to compete with the Macintosh operating systems available at the time. The final straw for Bob was the release of Windows 95 which, although antiquated nowadays, was a great step forward for Microsoft and came with both a better interface and more functionality than Bob could ever have dreamed of. In the end, Microsoft decided to drop the project, and Bob² was consigned to the backwaters of software history.