What’s the most efficient way to deride a technology product as a stinker and/or a flop? Easy: Compare it to Microsoft Bob. Bring up the infamous Windows 3.1 front-end for computing newbies–officially released fifteen years ago this week, on March 31st, 1995–and you need say no more. Everything from OS X to Twitter to Google Wave to (inevitably) Windows Vista has gotten the treatment.
Bob’s pervasiveness as an insult long ago transcended its brief period of prominence as a product. By now, it’s unlikely that the vast majority of people who use it as shorthand for “embarrassing tech failure” ever actually used it–any more than the average person who cracks jokes about the Ford Edsel has spent time behind the wheel of one.
But Bob didn’t start out as one of technology’s most reliable laugh lines. It may strain credulity given Bob’s current reputation, but back in 1995, even pundits who had their doubts about the software seemed to accept the idea that it was a sneak preview of where user interfaces were going. And even though Bob died just one year later, Microsoft continued to Bob-ize major applications for years–most notably every version of Office from Office 97 through Office 2003, all of which featured the notorious Office Assistant helper, better known as Clippy.
In its own odd way, Bob is ripe for rediscovery. Hence our fifteenth-anniversary celebration, which includes the story you’re reading; a guided tour of Bob in slideshow form; and memories of Bob and its offspring from Tandy Trower, who worked at Microsoft for 28 years. Whether you’re appalled by Bob, defiantly enchanted by Bob, or never knew Bob at all, read on–and let us know what you think.
(Thanks to Dan Rose, Rogers Cadenhead, and David Worthington for their help with our Bobfest.)
The Birth of Bob
Bob was an outgrowth of a product that debuted in 1991 and lives on today: Microsoft Publisher. The well-reviewed desktop-publishing software was the first Microsoft application to simplify complicated tasks via Wizards that took users through complicated tasks step by step.
“Just give me this duck to always be there and tell me what to do.”
After finishing up Publisher, its designers, Karen Fries and Barry Linnett, pondered what to tackle next. Their minds remained focused on making software more approachable to newbies. Which was a logical goal: In 1995, the average American didn’t even have a computer at home. (When Microsoft released Bob, it quoted projections saying that 46 percent of households would have a PC by 1997–and that was supposed to be a surprisingly high percentage.)
Fries and Linnett held focus groups and showed neophytes an interface with an animated waterfowl as an on-screen helper. In an interview with The Wall Street Journal, Fries remembered one man’s response: “This guy was very emotional about it–he grabbed my arm…He said, ‘Save all the money on the manuals and just give me this duck to always be there and tell me what to do.’”
The two then composed a provocative internal memo, arguing that Publisher was still too hard to use, and requested resources to develop a new interface for inexperienced users that would run on top of Windows. Bill Gates was intrigued. He gave the go-ahead for a project that was code-named Data Wizard at first, and then Utopia–and which eventually shipped as Microsoft Bob.

Stanford professors and Bob influencers Clifford Nass and Byron Reeves
Melinda French was named to head work on the product. A Microsoft employee since 1987, she became Bill Gates’s fiancée in 1993 and his wife in 1994–facts which led many to conclude that Bob was a lousy idea which never would have gone anywhere if it wasn’t for her involvement. But she was a Bob convert rather than its originator: Speaking of Fries and Linnett’s work, she told the Wall Street Journal that “they were breaking the rules of things we’d done in software before–I wanted to be a part of it.”
And while the Journal reported that there were doubters inside Microsoft, others both inside and outside the company drank the Bob Kool-Aid early. As work on Utopia proceeded, two Stanford professors, Clifford Nass and Byron Reeves, signed on as consultants. Their research showing that people attribute human-like qualities to machines proved influential.
Reeves was later quoted in a Stanford news release:
The question for Microsoft was how to make a computing product easier to use and fun. Cliff and I gave a talk in December 1992 and said that they should make it social and natural. We said that people are good at having social relations – talking with each other and interpreting cues such as facial expressions. They are also good at dealing with a natural environment such as the movement of objects and people in rooms, so if an interface can interact with the user to take advantage of these human talents, then you might not need a manual.

A Bob patent drawing
Nass and Reeves eventually joined Microsoft staffers on a press tour to promote Bob and the concept of “social interfaces” in general. “With a beta onscreen, these two academics summarized their research, which suggested that people found social interfaces helpful, friendly, and effective,” remembers PCWorld Editorial Director Steve Fox, who was briefed during a previous PCW tour of duty. “The two editors in the room were trying not to snicker at the presentation.”
On July 8th, 1994, Microsoft filed a patent for the idea behind Bob, detailing both the look and feel of its “real-world” interface and behind-the-scenes aspects like the editing tools used to create and animate animated assistants. It was the first of many patents the company would seek for animated helpers.
Ultimately, the thinking that went into Bob–from Fries’ talking-duck prototype to Nass and Reeves’ university research–resulted in an integrated personal-productivity suite in which cartoon characters led users through apps that used images of a home as backdrop. The characters were called “personal guides,” and included a dog named Rover (the default guide), a French cat, a rabbit, a turtle, a sullen rat, a gargoyle, William Shakespeare himself, and others. Each sat in the bottom right-hand corner of the screen, providing instructions in word-balloon form and performing bits of schtick as you used the software. (They spoke aloud, but only occasionally–a sound card was a recommended accessory, but it wasn’t mandatory.)
The package ended up with eight programs: a word processor, an e-mail program, a calendar, an address book, a checkbook writer, a personal finance info app, a household organizer, and a geography quiz. Microsoft envisioned that both it and third-party companies would release additional programs which could be installed within the Bob environment.
(For a full walkthrough of Bob–from the word processor to the e-mail service to the estate planner (!)–visit our guided tour.)
Fairly late in the game, the product apparently still didn’t have a name: According to the Wall Street Journal, Microsoft considered monikers such as Home Foundation, Essential Home, and Portico before its ad agency, Wieden & Kennedy, suggested the name Bob in September of 1994. Microsoft later touted the name as being “familiar, approachable, and friendly,” and acquired Bob.com from Boston-area techie Bob Antia so it could give users e-mail addresses at that domain. (After Microsoft Bob’s demise, it eventually struck a deal with another guy named Bob to swap Bob.com for Windows2000.com.)
Bob was personified as a smiley face wearing Bill Gates-like spectacles, but even though the software that bore his name was rife with animated characters, he wasn’t one of them. He appeared in the application itself only as a design element–for instance, he was the tag on Rover’s collar.
In October of 1994, a Microsoft designer named Vincent Connare saw a beta of Bob, and found the use of the staid Times New Roman typeface in its word balloons to be out of whack with the software’s playful personality. He began work on an aggressively casual font that wound up being dubbed Comic Sans; it didn’t make it into Bob, but was later bundled with Windows itself. Comic Sans ended up as the Microsoft Bob of typefaces: It’s famous mostly for being unloved.
Bob Revealed

Karen Fries (left, in Bob t-shirt) and Melinda French look pleased by Bob's CES unveiling in this AP photo.
On January 7th, 1995, Bill Gates strode onstage at the Consumer Electronics Show and revealed Bob to the world. He demoed the software and declared that it was a social interface, the first example of a new approach that would come to dominate computing. He even gave a sneak peek at a futuristic Son-of-Bob prototype from Microsoft Research: Peedy, a squawking 3D parrot who played Tears for Fears music in response to Gates’s spoken request.
Multiple Hollywood potentates were seated in the front row: Steven Spielberg, David Geffen, Jeffrey Katzenberg, and Barry Diller. Some observers took their presence as a sign that Bob represented a new convergence of the software and entertainment industries. “They’re seeing this kind of thing, the creativity here, and how we’re actually drawing on sound companies and animators who come with a Hollywood background,” Gates told the Associated Press.
Even if you were at CES but didn’t attend Gates’s speech, Bobmania was unavoidable. Flights heading into Vegas were supplied with Bob napkins, a plane towing a “Welcome Bob” banner circled above the Las Vegas Convention Center, and senior citizens wearing Bob sandwich boards trudged up and down the Strip.
Here’s coverage (yes, with Arabic subtitles) of Bob’s introduction from Stuart Cheifet’s Computer Chronicles PBS show:
In retrospect, the hoopla should have been taken with a humongous grain of salt: At later Vegas tech shows, Microsoft would hype such flops as Windows Smart Displays, Tablet PCs, and Smart Watches in similar fashion. Back in 1995, however, Microsoft-watchers responded to the Bob announcement respectfully. Even when they weren’t wild about Bob itself, they took it seriously as a sign of where software was going.
Industry newsletter Soft-Letter thought Bob was silly but significant:
At first glance all this twitching and prancing looks like a bizarre approach to interface design, but in fact the high-profile Bob characters have a purpose: They reinforce what Microsoft calls its new “social interface” between humans and PCs. In his CES keynote, Gates unveiled the intriguing new design principles behind Bob, principles that he predicts will become “the next major evolutionary step in interface design.” In essence, Gates suggests that the next generation of high-powered PCs will abandon traditional graphical desktops in favor of “social” interaction with humanlike agents that can understand, learn, and interpret what the user wants. Initially, these agents will display only rudimentary intelligence and problem-solving abilities, but they’ll quickly get smarter and more responsive as PCs acquire the necessary MIPS to run realistic simulations.
Many saw Bob as the next advance in software after the desktop-and-folders metaphor pioneered by Apple’s Macintosh a decade before. A Microsoft Canada employee told the Toronto Star that a study showed that 84 percent of users with Macs at home preferred the Bob interface. Several newspaper stories published at the time make mysterious references to Apple having a Bob-like interface of its own in the works.
“Bob is going to be another nail in Apple’s coffin…”
Analyst Charles Finnie of Volpe, Welty & Co. called Microsoft’s product a threat to the very existence of Microsoft’s competitor in Cupertino. “Bob is going to be another nail in Apple’s coffin unless Apple can somehow raise the standard yet again on the ease-of-use front,” he told the AP. That’s as striking a piece of evidence as any that Bob wasn’t immediately deemed a perverse joke back in 1995.
Bob Comes Home
Like many a Microsoft product before and since, Bob was announced before it was finished. The software didn’t formally arrive in stores until March 31st, 1995, almost three months after its CES premiere. It sold for $99–a little on the pricey side, even though it was an era in which software generally sold for more than it would in years to come.
But Bob’s pricetag wasn’t as significant an issue as hardware requirements. The program demanded a PC with a 486 CPU, 30MB of free disk space, and what the Puget Sound Business Journal called “a huge amount of memory”–8MB, or twice the typical amount that circa-1995 home PCs sported. Newbies would only be able to experience Bob if they owned unusually potent computers.
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March 28th, 2010 at 11:45 pm
I worked for a consumer electronics manufacturer that developed digital satellite receivers. In this time frame, we had a "living room" interface for our receiver that was part of Bob-think. This interface was graphics-heavy with pictures of functions instead of menus. The choice of graphical or menu was selectable by the user. I believe most chose menus.
From a technical standpoint, the graphical living room interface was difficult to do with the hardware/cost constraints of the day.
March 29th, 2010 at 7:02 am
wow, the fatal flaw was of Bob was in the last paragraph. Software that's built to make computers easier for beginners to use but require an expensive high end computer that only a much more seasoned user would have. Way to go microsoft, got any more good ideas?
March 29th, 2010 at 8:00 am
I’ve never heard of Bob. Most of the people I work with were still in high school in 1995, but I enjoyed this look at recent computer history.
I have a feeling that iPad will become the MS Bob of the coming generation.
March 29th, 2010 at 8:56 am
I have a copy of Bob still in shrink wrap and license #. I remember installing this OS on computers for schools and a boss’s home computer. I still laugh about this OS.
March 29th, 2010 at 9:26 am
Thanks for the look back at Bob. I do recall when it came out and as I worked in I.T. I had a good finger on the pulse of the industry feeling about it. Even Microsoft fans derided Bob from the start. It was apparent to all that it was geared towards kids and those afraid of a computer. Add to that the fact that it was layered atop Windows 3.1, and you had a doomed product. If they’d waited just a bit and included it with Windows 95 (released a mere 6 months later to much fanfare). Had Bob been on every Win95 CD (yes, OS’s were small enough for CD’s then), at least there would have been masses willing to give it a try. Then MS could have taken feedback and made a viable Bob 2.0. Instead, the separation of teams in Redmond prevented such cross-pollenation.
@Paul: The reason the iPad won’t be another Bob is that cross-pollenation does occur in Cupertino. Apple integrates all its products together and lets each one be marketing and support for the others. Also, you have the Steve Jobs vision behind each one; he simply won’t allow the iPad to fail, even if it has issues. He’ll fix it instead of abandoning it as MS did with Bob.
March 29th, 2010 at 10:37 am
Thanks for a wonderfully balanced account.
I’d like to add an example of how the implementation of the ideas behind Bob was deficient: If you entered three wrong passwords in a row, your assistant would offer to change your password for you! The zeal to make things simpler led to throwing the baby out with the bathwater.
March 29th, 2010 at 10:49 am
I remember Bob fondly, I had a relative with some limitations to movement who used it devotedly. I still believe the fundamental idea was sound, simple user interface. Even though the graphics were limited, the fundamental uses of the computer were simple and ready to use. Actually, I believe there is still room for such a product–many older and non-technical users still would benefit from a more graphic and simple user interface. It would actually be interesting with such advancement in graphics what an ungraded Bob would look like. Wish Microsoft with its resources hadn’t drop the project-it had a lot of potential.
March 29th, 2010 at 11:57 am
Ad for Microsoft Bob can be seen at Wired Reread:
http://www.wiredreread.com/2010/03/hi-bob-bye-bob.html
March 29th, 2010 at 12:23 pm
Wasn’t the name of the Stuart Cheifet show The Computer Chronicles (not the Computing Chronicles)?
March 29th, 2010 at 1:09 pm
“fragments of Bob survive in Windows 7’s word-balloon alerts.”
Try Balloon Help, introduced as part of Macintosh System 7 in 1991.
March 29th, 2010 at 1:29 pm
> Bob’s characters–seem to come straight from kindergarten.
> They’re drawn as if the program’s target audience were the
> under-12 set
That was the biggest problem, in my opinion. First, Microsoft looked down their noses at newbies and treated them like kids, instead of, for example, a lawyer who has never used a computer before. Second, they had software engineers create the art and animations, instead of artists and animators.
It was amazing to see them keep reusing these characters. The Windows XP search dog stunned me when I first saw it, which was in 2008 or so. I thought I was in a time warp back to Bob. I thought somebody had added that to the XP machine I was using. I couldn’t believe it was a built-in XP feature. Ironically, it’s so much harder to use than the Mac’s Spotlight search.
> I have a feeling that iPad will become the MS Bob of the
> coming generation.
Sheesh.
In its very first hour of being on sale, iPad outsold Bob. Just the preorders alone for iPad (even with a 2 per customer limit) will outsell TabletPC. Yes, every TabletPC ever sold. iPad is on pace to outsell both every Kindle and every Zune by the end of its first quarter of sales. So you’re already wrong.
It’s really a stretch to compare Bob and iPad anyway, especially because of running apps full screen. Apps ran full screen on the PC from 1982-1993, and many users still basically run that way today, using Alt+Tab to toggle between them. The Adobe apps even have their own desktop background on Windows. One of the first things many PC users ask when they switch to a Mac is “how do I maximize all my apps?”
March 29th, 2010 at 2:17 pm
Meanwhile, over in the Linux camp… Slackware… ;-)
– J. R. “Bob” Dobbs
March 29th, 2010 at 5:24 pm
I was working in tech support for a retail computer company when Bob came out. We fired up a copy so we could support the rush of sales the store management expected. I drove, while the other support staff watched.
After a quick run through all the ‘rooms’, I decided to create a short text document. When I started to save the doc, we all started counting how many steps were required.
About the time I hit EIGHT clicks, people started going back to real work.
When I finally finished on click number 17, I was the only one paying attention. And then there was none.
No worries, though, because we never had to support Bob, except to route callers through to the sales office for returns.
(OTOH, it was really easy to mod the official Bob logo into Microsoft Bob Dobbs, complete with pipe.)
March 29th, 2010 at 5:50 pm
I was seven when we bought a Gateway that came with MS Bob pre-installed. I remember my friends and I spending hours setting up our rooms and then comparing them.
It was great for a 7 year old, I cant imagine it being used to get anything done, for that I use Slackware 13 or Win7.
March 29th, 2010 at 10:35 pm
Played with Bob for a bit and iirc, my take was that rooms are a stupid metaphor. Hiding something off screen does not make it easier to find.
March 30th, 2010 at 5:02 am
Wow, Hats off to Harry this was a good effort in trying to compare the Ipad to Bob. I believe you missed the concept of Ideation to Market. The IPAD numbers alone speak for itself. Please next time more statistical and analytical information that would add weight to your comparison.
March 30th, 2010 at 10:05 pm
Great article. Microsoft did come back to the well one more time in a product called Creative Writer – http://en.wikipedia.org/wiki/Creative_Writer
It was a product for kids and it contained an imaginary world with a character who guided you through operations. The character was much more friendly and the cut down applications made more sense as a learning tool for kids. But it still didn’t catch on.
March 31st, 2010 at 6:38 pm
I had a lot of fun with Bob. It was completely useless for doing any actual work, but it was kind of creative, and more interesting than solitaire. I kinda miss Bob, but more as a pointless game than a GUI. Wish it hadn’t constantly crashed my system!
April 18th, 2010 at 3:10 am
Ah, Bob. This article brings back memories of my software engineer friend who took a job at Microsoft shortly before the Bob debacle. When Bob went belly up I teased her that it must have been her first project. It wasn’t. She is now semi-retired at age 49, living in her posh custom country home east of Seattle. I’m being laid off as my telecom employer downsizes. I guess she, and Bob, had the last laugh.
April 23rd, 2010 at 2:55 am
I read Nass’ and Reeves’ book about their research, and in itself it’s very good stuff.
But when you let academics and software engineers design a computer interface that’s supposed to be ‘social’, you get the sort of overly-literal ‘real life metaphor’ that Bob is. It’s like dressing up a brute as a clown and calling him friendly. Easy to do, but beside the point.
Many current applications actually implement a lot of the advice in Nass’ & Reeves’ research, but I wouldn’t call that the ‘legacy of Bob’, quite the contrary actually. Bob is like a blinking red warning light about what *not* to do.
The real challenge is about user-friendlyness, politeness, etc. Whether there’s a 3D parrot involved or not is totaly irrelevant for the user-computer relationship. No extremely brief or incomprehensible error messages, continuous useful feedback, intuitive interaction, responsiveness, those are the things that matter if you want people to consider a computer to be ‘friendly’ and easy to use.
I haven’t laid my hands on one, but I guess this is why the iPad is so succesful. It has a limited set of parameters, limited features and an intuitive, well-designed interface.
April 24th, 2010 at 6:22 pm
Bob was I realy nice try by that time. Today we have real assistants like the Denise at http://www.guile3d.com
July 2nd, 2010 at 6:21 pm
Microsoft could re-release it as Microsoft primary school…All the cartoons make it perfect for kids…
September 4th, 2010 at 8:48 pm
"I acknowledge that computer users in 2010 are infinitely more sophisticated than they were a decade and a half ago."
I read through your entire article, and found it very interesting and smart (just as the other ones), but this just makes no sense. If anything, people have been severely dumbed down since 1995…
October 20th, 2010 at 4:27 pm
I'm looking at my circa 1994 BOB cd that arrived with whatever storebought computer I was using at the time and I see that this version did not include a booklet. I recall that I tried installing it and running once. It was more trouble than it was worth, though not as bad as those AOL disks from the same era.
November 16th, 2010 at 8:15 pm
After reading this whole article I can't see anything that was revolutionary about MS Bob. It was basically a room metaphor with some annoying animated characters.
November 19th, 2010 at 4:22 pm
Well, I recently installed Windows 95 on an old computer I have and it works great! I also had a copy of MS BOB on hand, and installed it on the computer. It gets barely anything done, but it's still fun to use, and I can say "I have MS BOB" even after 15 years of it being released! Ah, vintage computing. Never fails to amuse me :)
March 4th, 2011 at 5:09 pm
Bob Wiley: I'm sailing! I'm sailing! I'm sailiiiiiing!
Dr. Leo Marvin: Keep sailing, Bob….
March 25th, 2011 at 6:34 pm
16 million units sold in one year, universal acclaim from non-geeks… Yup, you are completely effin wrong.
You LOSE!. Goodday sir!
April 5th, 2011 at 11:29 pm
Did you really just make a positive reference to Clippy?
April 8th, 2011 at 12:12 am
I had a Apple version of a shoddy imitation of Bob, which was designed for Mac OS6. It was peddled to poor, ignorant me, and my first Mac. When I found out that it could work with Mac OS7.5.3, which cam with my little Powerbook, I tried it for a while. What a sloppy and sham idea; rooms in the house for all users. Cabinets with drawers, desks, and so on. I quickly joined a Mac group, and once I had established my eager newbie credentials, openly invited scorn for being huckstered so easily, to test the group. The group stood by me and let me forswear henceforth never to use a Microsoft-imitating piece of software, especially one as poorly implemented and the one I had, the exception being any Microsoft product designed for the Mac, clumsy and bloated as they might be.
July 10th, 2011 at 11:01 pm
In 1996 I had a brand new Packard Bell. It was super fast with 32mb of ram and had a 166mhz cpu, wow it was the bomb. Anyway PB packaged a Bob-like interface too. Whist watching the movie with Gates in it I recognised the whole desk/room/filing cabinet interface. It wasn't very practical, as it was a resource hog, but it was far out at the time.
September 1st, 2011 at 12:42 am
When a new piece of technology is due to come out immanently, it creates a great sense of excitement and anticipation. At the moment, that focus is on Apple, due to the pending release of the new iphone 5.
September 1st, 2011 at 12:45 am
When a new piece of technology is due to come out immanently, it creates a great sense of excitement and anticipation. At the moment, that focus is on Apple, due to the pending release of the new iphone 5.
September 1st, 2011 at 12:49 am
Bob is realy great i must agree and you alll tooo.
iphone 5
October 11th, 2011 at 9:15 pm
Believe it or not, Bob really did teach me a lot about using the computer. I was just a kid when it was in use, but it was one of my favorite things to use on the computer. It was fun for me and taught me a lot…good for kids…not so for adults! :)
December 26th, 2011 at 6:31 am
It was a product for kids and it contained an imaginary world with a character who guided you through operations. The character was much more friendly and the cut down applications made more sense as a learning tool for kids. But it still didn't catch on.
January 28th, 2012 at 12:25 am
I worked for a consumer electronics manufacturer that developed digital satellite receivers. In this time frame, we had a "living room" interface for our receiver that was part of Bob-think. This interface was graphics-heavy with pictures of functions instead of menus. The choice of graphical or menu was selectable by the user. I believe most chose menus.Ghana news
February 22nd, 2012 at 11:51 am
This was the end all software for Microsoft. An easy version to completely eliminate Apple. Well it did not do that, but sure did get a lot of press and heavy marketing. Love the shirts.
February 23rd, 2012 at 6:47 am
Really remarkable article to read on.. I’m very impressed with this post. Looking forward for future posts.
Regards,
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