The Bob Chronicles

On its fifteenth anniversary, a look back at a legendary software flop.

By  |  Monday, March 29, 2010 at 1:54 am

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 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 for

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.

Still-shrinkwrapped Microsoft Bob. Courtesy of Dan Rose’s

In promotion for Bob–and even on the box–Microsoft kept coming back to the notion that it was a product so simple that it didn’t need a manual. Well, maybe: The software came with a 29-page booklet of instructions, but it was labeled as the first issue of Bob Magazine rather than as documentation.

What’s more, Microsoft Press, the company’s book-publishing arm, released a 210-page tome called At Home With Bob--which sounds like a lot of explanation for a package which supposedly needed none. (Microsoft Bob for Dummies–priceless title!–was planned but canceled before publication.)

As the product’s release date approached, Microsoft began a second wave of hype. It secured an enthusiastic endorsement of Bob from celeb/PC newbie Faith Ford–Corky Sherwood on Murphy Brown–and declared March 31st to be “Microsoft Bob Day.” Sears offered “technology makeover” advice to help consumers figure out which of Bob’s characters was best for them; CompUSA scheduled two days of Bob demos. Gateway 2000, NEC, Micron, and other leading PC manufacturers announced their intention to bundle Bob on their home machines.

Bob Goes Bust

“Bob’s characters…seem to come straight from kindergarten.”

For all that went right with Bob’s rollout, Microsoft made one critical strategic blunder. It had begun distributing copies of Bob to journalists in December of 1994, and apparently placed an embargo on reviews only through the CES announcement, not until the March 31st release date. Bob reviews therefore began appearing in January, which would have been dandy if they were glowing. But most were anything but. The tech journalists who actually tried Bob at length were generally far less impressed with it than the analysts who’d only seen it in demos.

Stephen Manes in The New York Times:

Bob is a poor neighbor. It stores its data in formats that better programs cannot easily import. It perversely reverses the positions of “OK” and “Cancel” buttons that have become standard. But then, a foolish inconsistency is a hobgoblin of Bob. Pressing Control-L in the home area lets you adjust the sound volume; doing the same thing when using the address book brings up the mailing list. Again and again, Bob tells you to do something but will not let you do it until you click an “OK” button.

William Casey in The Washington Post:

At this stage, Bob’s elements of customization are superficial. You cannot add your own guide characters, rename the ones Microsoft supplies, create your own constructs within rooms or build your own house. You can’t really even add your own room, other than one of Bob’s unsatisfying precooked versions.

John Dickinson in Computer Shopper:

Unfortunately, the room metaphor–as well as Bob’s characters–seem to come straight from kindergarten. They’re drawn as if the program’s target audience were the under-12 set, and much of their behavior will be unappealing to people seriously bent on getting a lot out of their PCs, or to adults of any kind, for that matter.

Michael Putzel in The Boston Globe:

If it were being introduced by anyone but the largest software maker in the world with the clout to command attention in any marketplace, you would never hear of this program, and I wouldn’t bother to review it. Bob would simply sink into the bog where bad products die quiet, unnoticed deaths.

It’s true that not every critic rated Bob as a fiasco. Larry Magid in The Los Angeles Times was somewhat less damning:

…Bob isn’t meant for the initiated. It’s designed for the millions of people who, each year, will start to use computers for the first time. Its interface should encourage exploration and its wacky characters may be just the comic relief that new users need to get over their initial phobias. But once people are beyond the basics, I suspect it will leave them cold and a bit bored.

And Walt Mossberg–then as now The Wall Street Journal‘s Personal Technology columnist–was genuinely upbeat:

Bob goes on sale tomorrow, and I recommend it to anyone who has found Windows frustrating or just too impersonal, whether you’re a novice or an experienced but casual user…This isn’t exactly a popular point of view in the computer press, or among the rest of the digerati–the technically adept, computer-oriented class. They’ve been pretty negative about Bob, calling it too simple, too corny, too condescending. But what’s really condescending is the conviction that anybody who doesn’t grasp or like today’s computer designs must be wrong. Like most first efforts, Bob has some flaws and drawbacks. But it’s a bold departure that attempts to give nontechnical people more control over their computers.

Overall, though, it’s painfully obvious that exposing tech enthusiasts to Bob was asking for trouble. Which is why it’s hard to figure out why Microsoft ran an ad for Bob in in the August issue of geek bible Wired, months after the software’s rocky reception. The tone was a tad defensive:

Fancy, schmancy. It’s feeling comfortable with your computer that really matters. That’s why there’s Bob. With Bob, you can customize your computer so it works the way you like to work. Bob features the newest thing in software: a social interface. Which is a fancy way of saying “a really nice program that’ll make your computer comfortable and friendly to you.” Bob will help you balance your checkbook, write letters, exchange electronic mail, keep a calendar, record addresses, play GeoSafari and access Windows-based programs. And do it all comfortably. Bob has personal guides–animated on-screen characters –that lead you every step of the way. In fact, Bob is so easy to use, it doesn’t even come with a manual. All you need is an 8-megabyte computer. To meet Bob for yourself, stop by a local software retailer and ask for Bob. Sure, Bob’s not fancy, but isn’t comfortable really where it’s at?

By then, it may have been clear that Bob was in trouble. Before Bob shipped, Microsoft had predicted that it would be a best-seller on par with hits such as Microsoft Works and Encarta. But according to retail research firm PC Data, only around 58,000 copies of Bob were ever sold. (By contrast, PC Data said that Microsoft moved around 2.75 million copies of Windows 95 at retail in the first month after its August, 1995 release.)

Great Greetings for Microsoft Bob. Courtesy of Dan Rose’s

In early 1996, Microsoft pulled the plug. It had released two Bob-related products: the Bob Plus Pack (which was later rolled into Bob itself) and Great Greetings for Microsoft Bob. But Bob 2.0, which had been in the works, never appeared. Neither did Bob for the Mac, a version which Microsoft had talked about before the Windows edition shipped. It was a remarkably brief run for a packages that had arrived to so much attention–especially given Microsoft’s famous willingness to stick with new products through multiple versions until they caught on.

“The biggest mystery, to me, is how Bob got killed so swiftly when Melinda French Gates was head of the Microsoft department that created it,” says tech author and unabashed Bob admirer Rogers Cadenhead. “I tried to interview her once, but Microsoft PR shot me down. I only had one question: Why did you allow Bob to die in 1996 –didn’t you know anyone at Microsoft with enough pull to save the project?”

Me, I don’t find Bob’s failure all that complicated: It was unappealing. Even if you buy into the notion of computerphobic grownups wanting to be helped by anthropomorphic animals and inanimate objects, the ones in Bob are grating and infantile. They’re poorly drawn and animated, make puerile jokes, and perform the same actions over and over in a rote manner that makes suspension of disbelief impossible. Even the sound effects are annoying. Microsoft may have gotten Hollywood to turn out for Bob’s premiere, but the software was created by engineers and academic researchers, not entertainment experts–and it shows.

Of course, there are other theories about why the software flopped. Including some raised by people who worked on the product:

Bob stuff: a mug (courtesy of Rogers Cadenhead) and baseball cap (courtesy of Ed Bott)

Bob was too much of a resource hog. This was Bill Gates’s own take. “Microsoft Bob was a product a couple of years ago that used on-screen cartoon characters to carry out tasks for people,” he wrote in a January, 1997 column. “Unfortunately, the software demanded more performance than typical computer hardware could deliver at the time and there wasn’t an adequately large market.”

Bob was poorly explained. “We spent a lot of time talking about the concept of the user interface, but we didn’t spend enough time talking about what Bob did,” former Bob Group Product Manager David Thacher told the Orange County Register, also in January of 1997. By which he meant that it wasn’t clear enough that Bob included a word processor, e-mail, check writer, and other applications.

Bob was a too-rough draft of a good idea. “The problem with radically new things is the first ones are usually atrocious,” mused Stanford’s Cliff Nass in a 1999 interview with the Knight Ridder/Tribute News Service. “But most atrocious products, if they’re new, have some redeeming features. [The industry] has very little tolerance for designs that are overall worse but have insight in them…It’s only concerned with things that are overall better,”

Pundits murdered Bob. “Tech influentials had started telling me that they were going to bury Bob,” wrote Monica Harrington, who managed PR for the product, last year. “They not only didn’t like it, they were somehow angry that it had even been developed. It was personal.”

Bob couldn’t live up to the initial hype. Harrington: “Bob was going to have to be a life-changing experience–and it wasn’t.”

“Tech influentials had started telling me that they were going to bury Bob.”

None of these diagnoses tell the whole story, but there’s probably some truth in all of them. Another point to consider:  Bob was around for only five months before Microsoft released Windows 95–an operating system that required less dumbing down than previous versions. “It’s important to think about Bob within the context of the time,” says Houston Chronicle tech columnist Dwight Silverman. “This was released before Windows 95 (thought it could be used with it), in the era of Windows 3.1, which was largely a shell sitting on top of DOS. There were a lot of replacement shells out there, such as Compaq’s Tabworks (which was pretty good), and a shell that came with Packard Bell PCs that used a similar “room” metaphor as Bob. When Windows 95 came out, though, such shells were rendered irrelevant–including Bob.”

Bob’s Their Uncle

Sons of Bob, clockwise from upper left: Clippy (Office 2000 version), Bob’s own Rover as Windows XP’s Search Assistant, the Microsoft Agent Merlin, and BONZIBuddy

Does Bob have a legacy? Its most obvious one is Microsoft’s multiple latter-day attempts to build Bob-like features into its most popular programs. For instance, far more people were exposed to Microsoft Office’s “Clippy” and the other Office Assistants than ever encountered Bob. (As Rogers Cadenhead has shown, the Office 97 Assistants are based on code so close to Bob’s that it’s possible to drag and drop the personal guides into Office.)

Almost seven years after Bob was announced, Microsoft brought back its protagonist Rover as the Search Assistant in Windows XP. He was jarringly out of place–especially in Windows XP Professional. But considering that XP is still the world’s favorite operating system, Rover isn’t out of work yet.

In “Bob and Beyond,” Microsoft veteran Tandy Trower writes about the Microsoft Agent, the Bob offshoot he spearheaded. The Agent was an open platform for building Bob-like characters for use in software and on the Web. It never truly caught on either. (One of the places it did get used was in Bonzi software’s BONZIBuddy, a piece of adware in the form of a talking ape with a reputation even worse than Bob’s.)

When Clippy was young, several newspaper articles appeared that he and other similar features proved that Bob had been ahead of its time. But the Assistants ended up as widely mocked as Bob. And all of Microsoft’s later social interfaces eventually died:  The company eradicated the Office Assistant as of Office 97, nuked the Search Assistant in Windows Vista, and ended support for Microsoft Agent in Windows 7 (although it ended up making the Agent unofficially available again due to popular demand).

What’s more, no other major tech company has found success with anything remotely Boblike, or even seemed interested in pursuing the idea. Bill Gates may have blamed Bob’s failure on daunting hardware requirements, but in 2010, even the most mundane netbook could run the voice-controlled 3D parrot he demoed in 1995–and none do. If anyone revived the idea of talking-animal guides today, every review would bring up Bob in the first paragraph. Not in a good way.

And yet…

Certain aspects of Bob’s interface live on, and usefully so. Bob archivist Dan Rose, who’s a fan–“the social interface gave a personal computer a more personal feel, and I think that was a very good idea”–makes a compelling case that fragments of Bob survive in Windows 7’s word-balloon alerts. Countless Web sites that step you through a process do so with menus that are reminiscent of Fries and Linnett’s Publisher and Bob interfaces. And when Apple wanted to ensure that the iPad was simple and approachable, it made some of the same decisions that Microsoft made back in the 1990s–most notably, it chose to have all apps run in full-screen mode.

I see aspects of Bob in Siri, a new iPhone app whose creators describe as a “personal assistant.” You speak requests into your iPhone; Siri listens, converts your speech into text, figures out what you meant, and responds with information. It works remarkably well. Yet the people behind Siri–who, as with Bob, include Stanford researchers–didn’t feel a need to jazz it up with talking animals knocking themselves out to be ingratiating. Like Bob, the program puts its information into conversationally-worded balloons, but they don’t emanate from a character. The balloons themselves are all the anthropomorphizing that Siri needs.

Which leaves me thinking that Bob’s biggest mistake was that it tried way too hard. I acknowledge that computer users in 2010 are infinitely more sophisticated than they were a decade and a half ago. But maybe even the newbies of 1995 would have been receptive to something more subtle than Bob’s cutey-cute menagerie. Something, in other words, that treated them like smart grownups who happened to be new to computers.

If Microsoft had pushed Bob in that direction–either initially or through upgrades–there’s a decent chance that it would have been remembered today as a landmark. Could it be that there’s some alternate universe in which new products are compared to Bob just as often as they are here–but it’s a compliment?

More Microsoft Bob on Technologizer:

A Guided Tour of Microsoft Bob

Bob and Beyond: A Microsoft Insider Remembers

The Secret Origins of Clippy: Microsoft’s Bizarre Animated Character Patents


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41 Comments For This Post

  1. Dave Says:

    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.

  2. Jennifer Kyrnin Says:

    Really remarkable article to read on.. I’m very impressed with this post. Looking forward for future posts.

    Corsages and Boutonnieres <h1></h1> <h2></h2> <h3></h3>

  3. scottm Says:

    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?

  4. iphone 5 Says:

    Bob is realy great i must agree and you alll tooo.

    iphone 5

  5. Paul Says:

    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.

  6. Lukeskymac Says:

    16 million units sold in one year, universal acclaim from non-geeks… Yup, you are completely effin wrong.

    You LOSE!. Goodday sir!

  7. dochalladay Says:

    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.

  8. JKT Says:

    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.

  9. tpzahm Says:

    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.

  10. david stoudt Says:

    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.

  11. Theis Søndergaard Says:

    Ad for Microsoft Bob can be seen at Wired Reread:

  12. Travis Says:

    Wasn’t the name of the Stuart Cheifet show The Computer Chronicles (not the Computing Chronicles)?

  13. Lawrence Person Says:

    “fragments of Bob survive in Windows 7’s word-balloon alerts.”

    Try Balloon Help, introduced as part of Macintosh System 7 in 1991.

  14. Hamranhansenhansen Says:

    > 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.


    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?”

  15. Sub-Genius Says:

    Meanwhile, over in the Linux camp… Slackware… 😉

    — J. R. “Bob” Dobbs

  16. Macartisan Says:

    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.)

  17. thepeng Says:

    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.

  18. gruhn Says:

    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.

  19. Designblog Says:

    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.

  20. Alex Andronov Says:

    Great article. Microsoft did come back to the well one more time in a product called 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.

  21. Aeolian Solo Says:

    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!

  22. Charles S. Says:

    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.

  23. Toon Says:

    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.

  24. Paul Says:

    Bob was I realy nice try by that time. Today we have real assistants like the Denise at

  25. firedemon7 Says:

    Microsoft could re-release it as Microsoft primary school…All the cartoons make it perfect for kids…

  26. dontsteponants Says:

    "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…

  27. guest Says:

    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.

  28. Tim at IMM Says:

    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.

  29. Scooter Says:

    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 🙂

  30. John G Moore Jr Says:

    Bob Wiley: I'm sailing! I'm sailing! I'm sailiiiiiing!
    Dr. Leo Marvin: Keep sailing, Bob….

  31. nick hiltunen Says:

    Did you really just make a positive reference to Clippy?

  32. GCNOLA Says:

    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.

  33. Arnum Says:

    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.

  34. iphone 5 Says:

    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.

  35. iphone 5 Says:

    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.

  36. Erin Says:

    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! 🙂

  37. Cheap VoIP Says:

    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.

  38. jackhopes123 Says:

    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

  39. iphone 5 pictures Says:

    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.

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