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Why I loved Microsoft Bob, Microsoft’s weirdest creation



The official Microsoft Bob logo.

This year marks the 25th anniversary of Windows 95, and people have a lot to say. My favorite part of Windows 95 was an infamous program called Microsoft Bob. It was a massive failure, but I loved it anyway.

A forgotten piece of Windows history

Windows 95 was a groundbreaking operating system that introduced many concepts that we still use today. Symbolic functions such as the start menu, the taskbar, Windows Explorer and the recycle bin were first displayed in Windows 95.

One thing that is not Microsoft Bob is fondly remembered from this time. It was released as a $ 99 CD-ROM in 1

995 and also shipped on some Windows 95 computers. The latter is how I first came across Bob as a kid, and it’s a relationship I still remember to this day.

CONNECTED: Windows 95 turns 25: When Windows went mainstream

What was Microsoft Bob?

A Microsoft Bob nursery desktop.

In the simplest case, Microsoft Bob was an alternative to the typical desktop surface. Instead of columns of icons and a start menu, your desktop was a virtual room. Anyone using the computer could set up their own room, which was part of a larger virtual house.

The bobsled experience started at the front door. To log in, you literally clicked a door knocker to open the password-protected user profiles. From the metallic clink of the door knocker to the blowing of menu clicks, the registration process was a nostalgic smorgasbord of sound effects.

The front door and the knocker in Microsoft Bob.
Sound effect property from Microsoft.

Once inside, your room appeared. There were also a surprising number of options when choosing a room. You can choose both the type of room (loft, garage, kitchen, etc) and the style (castle, haunted, retro, etc) you want.

The rooms were also very customizable. There was a large library of objects that you could add and move around to your heart’s content. You can also change the appearance of the objects. To explore the house, you simply clicked on one of the doors and selected a new room to visit.

The room menu in Microsoft Bob.

Here, too, the rooms functioned as desktops. The objects were links to Windows applications. Bob came with his own suite of apps. However, you can also add shortcuts to any regular Windows app. In the picture below I’ve added some games to the bookshelf.

The Clock menu on a Microsoft Bob Room desktop.

Your helpful “personal guide” watches all of this from the corner of the screen. Most people remember Rover the dog, but there were several other characters to choose from. They all had cute names and back stories. The personal guide acted as a start menu with a number of options that you can access at any time.

Rover the Dog shares information about Baudelaire on a Microsoft Bob room desktop.

Who was Bob for?

There are a number of well-documented reasons why Microsoft Bob failed, but his main flaw could simply have been a lack of self-esteem.

When you first look at Bob’s colorful user interface, fun interior design tools, and comic book companions, it seems like it is aimed at kids. It is likely not an interface you would use if you were familiar with computers.

There was a lot more potential for something like Bob in 1995 because not that many people had or were using computers. However, it probably seemed condescending to adults just starting to use them. Imagine you’re 35 years old and have a cartoon dog hold your hand while opening a calendar app.

Rover the dog

Microsoft’s failure to understand Bob’s audience was first demonstrated when tech journalists checked it out before Windows 95 started. Because Microsoft marketed Bob as software for “everyone”, tech-savvy journalists rated it as such. Of course, tech journalists didn’t need a simplified interface, so the reviews weren’t friendly.

Microsoft Bob could have worked as a niche product, but that was the opposite of what Microsoft wanted. All of marketing has been about how “everyone in your household” is going to love Bob. Instead of focusing on Bob’s strengths for beginners, Microsoft has viewed this as something everyone should take advantage of.

Marketing brochure for Microsoft Bob.
MobyGames

Why I loved Bob

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

Computers are something I learned very quickly (I remember vividly using MS-DOS to play games Commander Keen). Even so, I was only about 9 years old so I was the right age to appreciate Bob. I didn’t have a problem with the standard desktop, but Bob was just more fun. It didn’t seem condescending to someone so young either.

Rovers object decoration menu in Microsoft Bob.

One of my favorite things to do in Bob was redecorating the rooms and adjusting everything. I was the type of kid who rearranged my real bedroom just for fun. Years after Bob, I’ve enjoyed doing the same The Sims.

Another thing my sisters and I loved about Bob was this GeoSafari Quiz game that had its own personal elephant guide named Hank. It was educational but fun so I didn’t feel like studying.

A quiz in

The main thing that appealed to me about Microsoft Bob was having my own “space”. My room in Bob was an area on the computer that was entirely mine. I could make it look what I wanted, play games and just feel “at home” on the computer.

Actually, it’s a bit funny that I loved Bob so much because I wasn’t using it the way Microsoft intended at all. I don’t remember launching applications from the Bob interface, but the only apps that mattered to me were MS Paint and Hover.

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

The way I’ve used Bob has to do with why it ultimately failed: Microsoft didn’t understand who it was for. Bob would have benefited greatly from a more focused approach. Leaning into the playfulness and marketing it as a tool to teach kids how to use a computer would have been a better approach. Bob definitely made it easier for me to use a computer.

Bob’s permanent imprint

An animated gift from a burning kitchen desktop in Microsoft Bob.

While Bob was a failure (and made no mistake, it failed heavy)Parts of it lived on in future Microsoft products. The personal leaders are the most obvious example.

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

The infamous Clippy Assistant in Microsoft Office is the best known, but not the only one. In fact, Microsoft has brought Rover back as a search assistant in Windows XP. Many of us have a digital assistant these days – 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 isn’t that difficult to understand, and the clock app doesn’t have to look like a physical clock. Likewise, 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 practice to interact with software in a flow of conversation. Apps and websites walk you through a casual setup process. Siri and Google Assistant literally talk to us like humans. Bob just took the concept a little too far.

It is unfortunate that Microsoft Bob is always remembered as one of the company’s biggest mistakes. For me it is a nice reminder of my early days with Windows. Even the strangest products find a loving audience. I hope retirement treats you well, Bob.

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