Microsoft has had plenty of misfires over the decades; many are well-known, like Windows 8, Windows Phone, and the Zune. Other Microsoft stinkers are less talked-about, like the Microsoft Band or Groove Music.
But there’s one early failure you might have never heard of, or had forgotten about: Microsoft Bob. Released in 1995, it tried to provide a more user-friendly experience for computer newcomers. However, it tanked and was discontinued in less than a year.
Meet Microsoft Bob
Microsoft Bob, released in 1995, was a tool designed to help novices navigate their computers more intuitively. While graphical interfaces for computers weren’t new at the time, the idea was to make it easier to use the core functions of a computer without the learning curve. Rather than arbitrary menus and icons, Bob used the inside of a house as the layout to frame the tools on your PC: click the calendar, and you’d open the calendar app.
Bob was first released for Windows 3.1 (it launched before Windows 95). However, it was discontinued not even a year later, following dismal sales and widespread criticism.
I had never used Microsoft Bob before and wasn’t familiar with it, so I decided to give the software a try to see how bad it really was. It’s compatible with Windows XP, so I installed it in a virtual machine and took a full tour.
First impressions of Bob
Bob installed without issues; it was amusing to see the old-school installer that guided you through every step (more than today’s).
Upon launching Bob, you’re greeted by Rover the dog; you might recognize him as one of the assistants that appeared in Windows XP’s search function. He has you set up an account for Bob, explaining computer basics we all take for granted now (like why your password appears as asterisks).
After your account is made, Rover walks you through how the program works, including a “tour” (which is a series of speech bubbles to click through). You’ll notice two of Bob’s biggest problems at this point: the visuals and the constant text boxes.
Contemporary critics lambasted Bob for looking like it was created by a child, and I agree. Graphics were certainly more primitive back then, but the style looks like something designed to introduce kids to computers instead. The Letter Writer splash screen in particular is awful.
The other immediate issue is the number of text bubbles and how disruptive they are. During setup, and when you open a program for the first time, you have to click through tons of text going over the instructions. These tutorials don’t walk you through an example; they throw the info at you and hope you remember it later.
When a speech bubble is open, you can’t click much else until you click Next enough times to finish the text. Even clicking Exit to leave the current program is blocked, which is annoying.
Exploring the house of Microsoft Bob
During setup, you create your own “private room” in the house that contains data not shared with other users. Everything else is public for all Bob users.
The “house” starts with a few rooms, but you can add more to your liking. Most aspects of the house are customizable, letting you change the look of furniture, doors, the background, and more. You’re free to move items around, change their size, and otherwise tweak them.
This is all for visual flair, however. The core of Bob is a handful of apps:
- Letter writer (basic word processor)
- Checkbook (financial tracking tool)
- Household manager (maintenance lists, household records, vacation planning, and similar)
- Financial guide (similar to the household manager, but with tips on financial life milestones, buying a home, and similar)
- GeoSafari (basic educational game)
- Calendar (simple calendar and to-do list)
- E-mail (early email tool)
- Address book
- Clock (basic timers and alarms)
These are all basic tools that were handy for those using a computer for the first time. And thinking with that context, I see how this would have been helpful.
The letter writer includes a lot of pre-saved addresses for airlines, politicians, and other groups you might want to contact. Using a computer to keep track of household to-dos, and having advice about major life milestones alongside that, made sense for early computer users who might not have had internet access.
Bob’s tools worked with each other, too. For example, when you added a contact to your address book, you could select them as the recipient for a letter, and their birthday would appear as a calendar reminder. It reminded me of modern ways to make your contacts better, like adding their birthdays and addresses.
Bob’s email program was one of the first of its kind; it required you to subscribe to MCI Mail at $5/month to send up to 15 emails per month. The checkbook tool offered to let you pay bills online, which was also revolutionary for the time.
In addition to Bob’s own software, you can add programs from your computer as boxes into the house. But if you know how to do that, why would you need Bob?
Bob is functional, but has serious problems
I didn’t find Bob to be as broken, annoying, or useless as the general opinion would have you believe. Putting myself in the mind of someone who was using their first computer in 1995, I can see how the tools would have been useful.
However, Bob has several serious flaws (beyond what I already mentioned). While the programs themselves aren’t terrible for the time, the overall setup of Bob is strange. The graphics, customization, and simple geography game all make Bob come off as a program designed to help kids, not adults, learn computers.
Aside from the “private” room, there’s no reason to use more than one public room, since you can add all the apps to a single one. Customizing the look and rearranging items in the house could be fun for a child, but I can’t see an adult enjoying that.
Same with the various assistants—their “personalities” aren’t different enough to make up for the heavy-handed instructions. The one that walks you through the financial program guilts you into staying if you try to leave early or skip the tutorial, saying, “If you cancel, you’ll have to do it later!”
Certain items (like flow pots) are clickable, but then tell you that there’s no purpose to clicking on them. Why bother to have them there, then?
Bob is best left as a relic of the past
It’s not hard to understand why Bob failed; “awkward” is a good word to describe it. While its included software wasn’t terrible, it was presented in an ugly interface that wasn’t a fit for the target demographic. A few other aspects made the above issues even harder to stomach: the price, system requirements, and file format issues.
Bob required a fairly powerful PC for the time, excluding many from trying it. It also retailed for $100 ($215 in today’s money), which was a tall order—especially considering Windows 3.1 itself cost $149 for new customers or $79 as an upgrade from Windows 3.0.
Bob’s built-in tools saved files in their own format, meaning you couldn’t easily open a letter written in Bob using Microsoft Works or another word processor. Nobody wants to be locked into one app to access their work.
Bob launched in March 1995, with Windows 95 launching in August of that year. Windows 95 made huge strides in usability, leaving even less reason for people to use Bob.
Bob’s design had a lasting impact
Microsoft Bob’s design trickled down into other Microsoft offerings over time, though. Aside from Rover appearing in Windows XP, the idea of a friendly assistant led to the Microsoft Office assistants like Clippy. And you can trace a line from those to later assistance tools like Cortana and Copilot.
Finally, Microsoft Bob is also indirectly responsible for the creation of the infamous Comic Sans font. A designer at Microsoft thought Times New Roman was too serious a font for a cartoon dog to use in Bob. In response, he came up with Comic Sans, which wasn’t included in Bob but shipped with later versions of Windows.
Like many Windows features that are gone for good, Bob never carved out a place for itself. But it’s fun to look back on these missteps and see what they were going for.