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Why I Loved Microsoft Bob, Microsoft’s Strangest Creation



The official Microsoft Bob logo.

This year, Windows 95 is 25 years old, and people have a lot to say about it. My favorite part of Windows 95 was a notorious program called Microsoft Bob. It was a huge failure, but I still loved it.

A forgotten piece of Windows history

Windows 95 was a groundbreaking operating system that introduced many concepts that we still use today. Iconic features, such as the Start menu, Taskbar, Windows Explorer, and Trash, all first appeared in Windows 95.

A thing like is it not remember from these days is Microsoft Bob. It was released in 1

995 as a $ 99 CD-ROM, and it also came with some Windows 95 computers. The latter is how I first stumbled upon Bob as a child, and it’s a relationship I remember to this day.

RELATED: Windows 95 turns 25: When Windows went Mainstream

What was Microsoft Bob?

A Microsoft Bob child desk.

At its most basic level, Microsoft Bob was an alternative to the typical desktop interface. Instead of columns with icons and a Start menu, the desktop was a virtual room. Everyone who used the computer could create their own room, which was part of a larger virtual house.

The Bob experience began at the front door. To log in, you literally clicked on a door knocker to open the password-protected user profiles. From the metallic clink of the door knocker to the bubble in the menu clicks, the login process was a nostalgic smorgasbord with sound effects.

The front door and the knocker in Microsoft Bob.
Microsoft Sound Effects Features.


When you were inside, your room arrived. There were a surprising number of choices when it came to choosing a room as well. You can choose both what type of room (attic, garage, kitchen and so on) and style (castle, haunted, retro and so on) you wanted.

The rooms were also very customizable. There was a large library of items that you could add and move as you like. You can also change what the objects looked like. To explore the house, you simply clicked on one of the doors and chose a new room to visit.

The room menu in Microsoft Bob.

Again, the rooms served as desks. The objects were shortcuts to Windows applications. Bob came up with his own suite of apps, but you can also add shortcuts to any standard Windows app. In the picture below, I added some games to the bookshelf.

Your helpful “personal guide” looks at all of this from the corner of the screen. The one most people remember is Rover the dog, but there were several other characters you could choose from. They all had cute names and background stories. The personal guide served as the Start menu, with a lot of options that you can access at any time.

Rover the dog who shares information about Baudelaire on a Microsoft Bob room desk.

Who was Bob for?

There are a number of well-documented reasons why Microsoft Bob failed, but its main shortcoming may simply have been a lack of self-awareness.

When you first look at Bob’s colorful interfaces, fun decorating tools, and cartoon companions, it seems to be geared toward children. It’s probably not an interface you would use if you know computers.

There was much more potential for something like Bob in 1995 because not many people had or used computers. But it probably seemed condescending to adults who were just starting to use them. Imagine you are 35 years old and having a cartoon dog holding your hand by opening a calendar app.

Rover dog's

Microsoft’s failure to understand Bob’s audience first appeared when tech journalists reviewed it before the launch of Windows 95. Since Microsoft marketed Bob as software for “everyone,” tech-savvy journalists reviewed it as such. Of course, technical journalists did not need a simplified interface, so the reviews were not kind.

Microsoft Bob could have worked as a niche product, but it was the opposite of what Microsoft wanted. All the marketing was about how “everyone in your household” will love Bob. Instead of focusing on Bob’s strengths for beginners, Microsoft pursued it as something everyone should use.

Marketing brochure for Microsoft Bob.
MobyGames

Why I loved Bob

The first computer I remember using was a Gateway 2000 running Windows 95. I’ve had a computer for most of my life, but I also remember when they were new.

Computers are something I picked up very quickly (I clearly remember using MS-DOS to play Commander Keen). Still, I was only about 9 years old, so I was the right age to appreciate Bob. I had no problem using the standard desktop, but Bob was just more fun. Nor did it seem condescending to someone so young.

Rover's menu for object decorations in Microsoft Bob.

One of my favorite things to do in Bob was to renovate the rooms and customize everything. I was the kind of kid who rearranged my real bedroom just for kicks. Years after Bob, I enjoyed doing the same thing in The Sims.

Another thing my sisters and I loved about Bob was GeoSafari quiz game, which had its own personal elephant guide named Hank. It was educational, but fun, so it did not feel like learning.

A quiz in

The most important thing that appealed to me about Microsoft Bob was to have my own “space”. My room in Bob was an area on the computer that was completely mine. I could make it see how I wanted, play games and just feel “at home” on the computer.

Now, it’s actually a little funny that I loved Bob so much because I did not use it at all the way Microsoft thought. I do not remember that I started applications from the Bob interface, but then the only apps I cared about were MS Paint and Hover.

Joe's childhood bedroom and gargoyle personal guide in Microsoft Bob.
My favorite bedroom style and personal guide.

The way I used Bob started why it finally failed: Microsoft did not understand who it was for. Bob would have benefited greatly from a more focused approach. Leaning into playfulness and marketing it as a tool to teach children how to use a computer would have been the better way. Bob definitely made me more comfortable using a computer.

Bob’s lasting imprint

An animated gift of a kitchen computer on fire in Microsoft Bob.

While Bob was a failure (and make no mistake, it failed hard), parts of it lived on in future Microsoft products. The personal guides are the most obvious example.

Clippy asks if you need help writing a letter.
The virtual assistant Clippy. Used with permission from Microsoft.

The infamous Clippy Assistant in Microsoft Office is the best known, but it’s not the only one. In fact, Microsoft actually took back Rover as a search assistant in Windows XP. Today, many of us have a digital assistant – you probably use Siri or Google Assistant every day.

While some of the ideas used in Bob were ahead of their time, the execution was wrong. A traditional desktop interface is not that difficult to understand, and people do not need the clock app to look like a physical clock. In the same way, user profiles work just as well as rooms in a virtual house.

What is clear, however, is that Bob’s social and more personal concepts were smart. It is now common to interact with software in a call flow. Apps and websites take you through an installation process with a relaxed language. Siri and Google Assistant are literally talking to us humans. Bob just took the concept a little too far.

It’s unfortunate that Microsoft Bob will always be remembered as one of the company’s biggest mistakes. For me, it’s a good memory from my early days with Windows. Even the strangest products can find a loving audience. I hope your retirement treats you well, Bob.

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