Microsoft Bob: Microsoft's biggest flop of the 1990s

7 days ago (dfarq.homeip.net)

Microsoft never really left the dream of creating Bob behind. If you look at their Virtual Reality Portal it is basically a modern version of Bob where you start in a livingroom and need to go into into other rooms to perform certain task. To start apps you eg. need to pick them from a book shelf. Essential the same a Bob.

A few images for reference. Notice that you start MS Paint same way in the VR portal and Bob.

VR Portal: https://onewindows.es/wp-content/uploads/2017/10/windows-mix...

Bob: https://static1.howtogeekimages.com/wordpress/wp-content/upl...

  • Its funny that as soon as microsoft need to make an alterate UI for computers they always reach for the home as an analogy. Are they really that short of creativity that rooms full of stuff is all they can imagine computers as?!

    • If you look at their Metro UI that was very innovative, and looked a lot like "real stuff" less than the equivalent iPhone/Android UIs at the time, from memory.

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    • Rooms with stuff are natural, we all live in them. And even Game devs tend to implement them as interfaces, because it's simple to understand for beginners and laymen. Any innovative interface has to build knowledge and understanding with the users first, and that usually fails.

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  • FWIW I actually really enjoyed that VR Home concept, far more than any of the current ones. At the time that I had the headset that supported that and still ran windows I was enamored with the space and spent a lot of time in the loft space, the one at the top of the skyscraper.

    I did as much of my computing in that space as possible, pulling up multiple desktop windows and floating applications and pinning them places. On one wall I had the Zune software with my whole music library, and my music played from that place, so I imported 3d models of speakers (I managed to actually find an end user use case for that default Windows user folder and I still as an admin and dev wonder why it's a default) and stuck them next to the app and they persisted. I'd drag discord around with me and I could even access the screen of my phone by bringing up Your Phone.

    I found it really kind of nice to use, and I wish the space had been more capable. Able to take more object formats, able to handle more vertices, I wish I had been able to boot directly to the virtual environment and eschew the step of switching between desktop and virtual mode. It also visually paused basically every app and desktop you didn't specifically keep active, except for Zune--that would go into Mixview and look cool as hell on the wall.

    I miss it, and I'm sad they killed it and I'm not aware of an experience like it for linux on an openish device atm.

We had Bob in an attempt to make my technophobic mother capable of using the computer.

My main memory of it was that it allowed you to add shortcuts to other installed programs, so I added the few games on the computer to Bob. This used way too many resources, causing Bob to crash and me being unable to get into my profile to fix it. It may have broken the program for anyone else using it too, I can't recall. Relatively standard behavior crashing the program far beyond their target market's ability to fix it.

First Windows computer I ever used had something like this, called Packard Bell Navigator. It was... interesting but ultimately an annoyance to use.

Looking at screenshots, Bob appears to be a more childish and cartoony version of the concept. I can see why it didn't fair well.

https://youtu.be/pwTIbYV_q6I around the 12 to 13 minute mark shows the Navigator interface.

  • Ugh, Packard Bell. Being our first computer, we had no idea that Navigator program was pointless until months after. And I think it was another year before we realized it was capable of true color resolution (It shipped with 256 colors as the default).

  • Version 1.0 of Packard bell navigator in that video reminds me of the Macintosh "at ease" software I used to see in schools.

    Totally off topic, I'm reminded that a high school friend gave me an old Packard bell machine for free once, and I ran OpenBSD on it for years. I got some ISA NICs and used it as a firewall.

    • Oh gawd I remember Mac "At Ease." That was the dumbed down lockdown software they used to make the computers at the school labs fun proof.

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  • Well, as a kid, I loved it.

    It was probably awful but I didn’t care at all it had extreme 90´s vibes. All of my games were in a space room or whatever I remember. I was 6 or 7 and I discovered computers. Everything was cool. Packard Bell Navigator was in everything so it was cool :)

    Yes it’s nostalgia.

  • The first computer that I bought (in 8th grade, after saving for a couple of years) had Packard Bell Navigator. It was a sort of full-screen program in Windows 95 that you'd use to launch other programs, although it could do a few other things in-app.

    It was ... odd. I opened it once or twice and deleted it.

    • You just unlocked a core memory for me. I remember that house so well but haven't thought of it in decades!

  • if Microsoft Bob was too cartoony for you, you could also go with a cartoony puppy, or a cartoon wizard!

    I worked with a software developer who LOVED that puppy - way more than I loved MOPy fish (rip)

Us kids loved it. Spent a lot of time configuring rooms, theming them, exploring all the features. The most intriguing one was a mailroom, but that's because it asked to configure your modem and email server settings which I couldn't do. Had separate profiles for each of us in the family and our friends; but we soon learned you could reset anyone's password by saying you forgot it. Once the griefing started it lost some appeal, but I still have only fond memories of MS Bob.

  • Yes, I have only positive memories of it! Customizing the house was like a primitive version of The Sims.

> Microsoft included an encrypted copy of Bob on Windows XP installation CDs to waste space to discourage piracy.

This feels like an urban legend made up after the fact.

It would be way easier to just generate random bytes, and nobody could ever tell the difference.

Especially since no decryption key exists.

It's just a funnier story if that's the only thing Bob was ever good for...

Bob is always easily criticized but it was actually a fun and cute software that included the basic versions of what a lot of people needed, like a Word Processor that wasn’t at the same level as Works (or Office). Almost everyone who makes fun of it never used it. But it was an early mash up of a few different things that all survive in various ways in other products. For example the home in Bob, which is often the main thing people make fun of, draws on the same fun people get when they’re designing spaces in the sims or whatever else.

It gave us Comic Sans, which had a notable impact on culture. I wouldn't call that a flop.

  • It also gave us the world’s greatest example of poorly thought through security practices.

    You can set a password on your Bob account. If you fail to enter the right password three times in a row, Microsoft Bob lets you reset the password, no further questions.

  • The funeral director at my father’s funeral used comic sans for everything.

    A flop no but used hilariously for a things it shouldn’t be. One of the most divisive typefaces ever.

    I like it.

    • That's hilariously bad. Our sweet old lady office manager 2 jobs ago used comic sans for every announcement.

      Babies and new employees and that sort of thing it was fine. But using it for death notices of employees family members, with frowny face emojis, was a bit much. She was so sweet, but so very very oblivious.

General Magic and Magic Cap [1] are not mentioned in this article.

If you know anything about Microsoft, you know they don't innovate. That was true in the 90's when Bill Gates was running Microsoft, and it is true under Nadella. Anything they do is ALWAYS in response to a competitive threat. So what was the competitive threat that spurred Microsoft Bob? It was the "social interface" of General Magic's Magic Cap operating system. When that flopped Microsoft cancelled Bob.

[1] https://en.wikipedia.org/wiki/Magic_Cap

  • I think General Magic might've been onto something. From what I've seen, BOB looked so childish that it was likely insulting to adult users. General Magic had a crisper UI (partly because of the b/w nature of the devices) that felt more like the iconography of a late-80s copy machine.

    • I've got an old Sony Magic Link; one of the devices running the Magic Cap software. Both suffered from similar problems.

      For starters the spacial interface is so cumbersome it makes all interactions with the system tedious. The first time you walk through the system it's cute but when you need to painstaking navigate to a particular room to do something it's just frustrating.

      The hardware could not keep up with the demands of the interface. The PCs that shipped with Bob (in my experience) could not run it without paging and thus slowed to a crawl running it. Launching a program from Bob just resulted in interminable waits while the disk thrashed. The Magic Link is painfully slow and does not demonstrate the OS well at all.

      Magic Cap was really no less insulting to users than Bob. It wasn't as cartoony but its tediousness wasted your time. The sluggishness of the hardware did not help. Even the early Newton MessagePads were snappier devices and their UI didn't make you tediously navigate through a virtual space.

  • > If you know anything about Microsoft, you know they don't innovate.

    Longhorn failed because MS tried to be too innovative within the scope of a single OS release. In some ways Microsoft was more innovative under Ballmer than Nadella--see e.g. the radical Midori OS that Nadella killed, or Microsoft Research's highly productive Silicon Valley campus that Nadella shut down.

    • > Microsoft Research's highly productive Silicon Valley campus

      What are some notable examples of innovations that came from MSR Silicon Valley campus? In my opinion nothing notable has ever come out of MSR, regardless of campus. Microsoft is needing to rely on third parties such as OpenAI because MSR seems incapable of contributing anything notable to AI.

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  • This idea may just have needed better technology. We should try these things again.

    There's a bunch of stuff that didn't really work that well 30 years ago that we use today

I broke my dad’s computer editing the registry to configure Microsoft Bob to display “the computer is a toy, not a tool” at the top. He had to call an older kid from church to come over and fix it. I was hoping that kid would be impressed and rightfully got nothing. Good memories.

How did blogspam with zero screenshots get upvoted? Actually seeing the product helps understand why it flopped.

  • The light-grey text on white background really enhances the vibe of the piece, too

"And then they released Microsoft Bob. They should have named it Microsoft Bomb, because it bombed. But if you take one letter out of Bomb, you get Bob. So they almost got it right."

So proud of this one they had to explicity point it out. Thank you though, I never would have made that connection.

Bob was hilariously bad.

But I never got the impression it was more than a weird experiment, failed, but I dunno about "biggest flop" as the stakes weren't that high. 95 was coming and clearly the way forward.

  • It's a clickbait title.

    If we were serious about biggest flops, we'd be talking about my beloved Lumia WP.

    • The Lumia series of phones had solid hardware but Windows Phone OS was crap, so the product line itself could never be competitive enough; I mean Nokia singlehandedly died at the braindead decision to go with Windows Phone and not Android. So if you're talking about phones, then I'd say it was Windows Phone OS that was the biggest flop, not the hardware.

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Let's use the clickbait title as a brainstorming prompt: what do other folks think is a better candidate for the biggest flop [in tech] of the 1990s?

Also, I kind of wish Microsoft Bob failed a little harder— the agentic stuff I'm hearing about these days sounds like the kind of software assistants they tried in the 90s, and I fear they have the same likelihood of poor execution.

  • > what do other folks think is a better candidate for the biggest flop [in tech] of the 1990s?

    VAX 9000, OS/2 2.0, OS/2 Warp 3, OpenDoc, Kaleida, Apple Newton, Pippin, 3DO, Philips CD-i, Sega 32X, Sega Saturn, Atari Jaguar, Amiga CD32…

    • Oh if we're going through that sort of list....

      - Virtual Boy, Atari Lynx,

      Hardware:

      - AMD Interwave. practically ruined Gravis and left us with years of Creative gobbling up any competitor i.e. Ensoniq, Aureal... FFS we had to wait for VIA to make something competitive to Creative's offerings, outside of 3-ish beautiful Cirrus Logic 4624/4630 cards, before the Envy24 became a thing.

      - Speaking of Cirrus Logic, The Laguna CL-GD546X series of chips; those things used RDRAM in the mid-90s and it contributed to Cirrus exiting the video market.

      - Speaking of Creative, the 3D Blaster VLB. They exist, (heck IDEK if the original rebel moon came any other way,) but they are rare as hell which means they probably flopped hard.

      - (Kinda) the Matrox M3d (and the VideoLogic counterpart). It wasn't a terrible product in and of itself but a Riva 128 was faster (if uglier) for most cases and gave you 2D as well, and they came out around the same time. [0]

      - Most 'cartridge disk' drives aside from the Zip[1]. You can possibly throw SuperDisk/HiFD into this category too.

      - Intel i820 Chipset (It's 1999!). I'm not referring to the 'lemon' aspect (i.e. when an MTH was used for SDRAM, the RDRAM was reliable... AFAIK with two slots instead of 3) but in general there was almost zero uptake due to the cost of RDRAM and Intel's recalcitrance led to both AMD gaining ground as well as VIA/SiS getting opportunities to be more competitive in the chipset space (SiS 630 was cheaper than 810E and just as good for normal users, Via's Apollo Pro 133A both supported 133Mhz FSB and gave an AGP slot, as well as IDE corruption with an SBLive... I think i815 was 4-6 months after VIA stuff was selling, and remember back then 6 months was an eternity...)

      Also I should note that the Saturn was mostly a flop in the US (Can't speak for EU.) but in Japan it held up well thanks to native publishers, the Saturn had a lot of great 2D games we never saw here, (thanks to the same guy that ironically caused the relative dearth of good RPGs for the PS1 before he moved from Sony to Sega...) also the ability to play CD+G (gotta have that karaoke) and I think? it could do VCDs which were bigger over there... all that stuff helped a lot and the Saturn outsold there till around 1997 IIRC.

      [0] - That said, wow, remember when 3d processors didn't even need a heatsink? I feel old...

      [1] - Zip had reliability problems, but certainly was not a flop.

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    • I managed to get my hands on a Turbo Graphics 16 console. Zero complaints. Bonks Adventure was so fun. It never took off.

  • Bigger assistant/agent flop of the nineties was General Magic https://en.wikipedia.org/wiki/General_Magic Packed with smartest engineers and usability people from the valley. Idea was to use smart remote agents "working for the user". Burned $200mil of 1995 money developing absolutely nothing usable.

    • I recently read the story of the Magic Link: https://commoncog.com/c/cases/general-magic/

      > When General Magic finally shipped in 1994 — under the threat of Apple’s Newton — they hadn’t made the Pocket Crystal that Porat first dreamed of in 1989. Instead, they released something they called the Sony Magic Link. It weighed 1.5 lbs (0.68 kg) and was priced at US$800 (US$1560 in 2022 dollars). It offered futuristic features like a touchscreen, downloadable apps and animated emojis — the first of its kind. Fadell thought it would be revolutionary — people could now carry a personal computer with them wherever they went. But nobody bought it. In the end only three to four thousand Magic Link devices were sold, and mostly to family and friends.

      There's a documentary too: https://www.youtube.com/watch?v=uTdyb-RWNKo

  • Clippy the Office Assistant. Similar idea to Bob, but more irritating.

    Also, The Microsoft Network. This was a competitor to AOL that came out just as the WWW was exploding. It gave us the "MSN" abbreviation that we still see today, but otherwise disappeared without a trace.

  • > what do other folks think is a better candidate for the biggest flop [in tech] of the 1990s?

    The CueCat.

    • What qualifies as being from the 90s? The CueCat was definitely underdevelopment in the 90s but wasn’t publicly released until 2000.

    • IBM's Workplace OS was a couple $Billion flop.

      I'd also add Network Computers and "push technology" e.g. Pointcast.

  • A whole bunch of telecom technologies like WAP (https://en.wikipedia.org/wiki/Wireless_Application_Protocol), ISDN (https://en.wikipedia.org/wiki/ISDN) and ATM (https://en.wikipedia.org/wiki/Asynchronous_Transfer_Mode). Thankfully too since they were ugly, closed and expensive.

    • Is WAP really considered a failure? Or just a transitional technology for an era of low-powered mobile devices? I downloaded my fair share of games and ringtones from "wap dot" sites.

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  • Hmm.

    WebTV might be up there, similar for Monorail PC.

    Both fairly quickly got obsoleted and any 'volume' they hoped to reach in consumer space was quickly cannibalized by similar but more profitable models (i.e. E-Machines and their steep internet contract discounts.)

    Nx586 was a bit of a flop as a product on its own (even funder Compaq didnt really ship many) but overall the R&D transformed AMD when they acquired NexGen and used the second iteration of the tech for the K6.

  • Microsoft Mira was a failure with production units shipped by 3rd parties.

    https://en.wikipedia.org/wiki/Smart_Display

    • That’s insane they thought a more expensive tablet was a market as opposed to a stand alone tablet.

      The remote viewing is coming back though. PlayStation Portal comes to mind which is just a remote controller and screen for a PS5. It’s considerably cheaper than the full device, of course, because that would be insane if it weren’t, _Microsoft_

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  • I'd think "Synchronys SoftRAM" could be considered a bigger flop in terms of the actual quality of the product, but it was a successful scam.

I have a vague recollection of a piece of software distributed by Bank of America in the mid-to-late 90s that featured an interface similar to Microsoft Bob. From what I remember, it was similar to Quicken. Was never able to find any information about it, and granted I was probably 5 when I found it on the family PC so the memory is a little fuzzy, but seeing these old design languages from that era of computing is always neat.

The product manager for Bob, Melinda French, would go on to marry Bill Gates, which goes a long way to explaining why Bob was the fetch that Microsoft kept trying to make happen. Its cutesy avatar technology would go on to power Clippy, the Windows XP search dog (actually a 3D version of one of the Bob characters), and be available as an API for use by third parties (most famously Bonzi Buddy).

I have a pristine shrink-wrapped copy of Microsoft Bob on my office shelf next to my shrink-wrapped copy of MS 3D Movie Maker.

There is a shrink wrapped box of Bob on display at the Computer Museum of America in Roswell, Georgia (Metro Atlanta).

Being slow is pretty bad but I have a suspicion that the name alone was bad enough to doom it.

Seems like Steve Jobs made the vision of a computer that absolutely anyone could use a reality with the IPhone. It would be interesting to see the design process of the IPhone and Bob side by side. What were the differences in methodology that lead to one being a disaster and the other being a legendary success.

  • I have elder relatives who have trouble using the iPhone, in particular after the flat UI was introduced with iOS 7. The UI and behavior can be quite inscrutable.

    • Agreed and I have witnessed many users struggling with all modern UIs. Android and iOS are far too much for most people if they have to do anything more than opening an app. To make it worse, the UIs are always changing drmatically.

I'm gonna have to be "that guy" here, because the contrast on this page is so low that I can barely read it :(

Bring back a version of this to help aging seniors deal with increasingly complex interfaces.

  • Seniors today were professionals using technology 20 years ago.

    In many ways interfaces have remained pretty static since then.

    The only real innovation was the iPhone, but it’s just a more responsive multi touch palm, to some degree.

    We still use windowing computers with mice/trackpad and keyboard, have pocket computers with apps and touch screens, and interface with more less the same browser with URL bar.

    We maybe are on cusp of VR and that will be a sea change in interfaces, if it ever comes to pass. And voice commands, but pretty limited function so far

    That’s from the 90s to today.

    Compare that to 60s to 90s, where you barely had desktop calculators, and used magnetic tape and maybe punch card inputs:

    https://www.computerhistory.org/timeline/1965/

    • We're probably heading for a future where seniors know what a filesystem (and other concepts we take for granted) is and younger generations don't because they've been trained to use iOS and Android fully.

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    • >Seniors today were professionals using technology 20 years ago.

      This is correct. Folks, VisiCalc was introduced in 1979, when today's ninety-year-olds were 44. They had not even lived half their current life.

    • > The only real innovation was the iPhone, but it’s just a more responsive multi touch palm, to some degree.

      You can’t just treat this as a throwaway line. Touch interfaces signal a fundamental shift in the way people interact with computers. You just take swipes and gestures for granted. Have you watched a senior try to interact with the modern web? The interface is not only the buttons of the browser, but the page itself. Today we have shifting interfaces that move because of lazy load ads. We have popups that one needs to understand how to close. We have essential functions buried behind an arbitrary “hamburger” menu icon. We have sites that hijack the back button. Sites that deliberately try to deceive. And lots of software (including Microsoft apps) has shifted to a cloud model. This becomes an inextricable aspect of the interface itself. Suddenly, there’s no means to “save” and old “digital paper” model/metaphors have given way to “infinite web page” documents.

      I spend a lot of time with seniors and see firsthand the roadbumps and dead ends they face.

    • That's a weird take, we have enough stories of people growing up with mobile phones having less of a clue about desktop OSes than people aged 30-60. We have other people (seniors now) who never really clicked with computers in the 90s-2010. There are so many groups who would fall into the category of benefitting from this.

  • I remember when the first iPad came out, and the tech press marveled at how easily seniors could understand it. This no longer applies to modern iOS.

    We don’t necessarily need Bob. We just need an iOS 1 mode, skeuomorphic design and all. Back when the camera app only had a photo or video switch, a take photo button, and a gallery button.

  • that's an idea - a version of it on social media to remind them to go out and touch grass instead of believing every conspiracy theory.

"Microsoft Bob presented screens showing a house, with rooms that the user could visit containing familiar objects corresponding to computer applications, such as a desk with pen and paper and a checkbook. Clicking on the pen and paper would open the system’s word processor"

Seems like some aspects of the experiment survived and were hugely popular: folders, clipboard, cut, paste, etc..

  • MS Bob didn’t invent those things. It just grafted them onto a crude gui metaphor that tech companies are still trying to find a buyer for: “What if the UX was as close as possible to the physical world?”

    You don’t open a file, you “walk” to a “filing cabinet”, “pull the drawer out”, and “reach in and pull out a specific piece of ‘paper’”.

    You don’t make a phone call, you sit in virtual meeting space with virtual bodies while wearing a mocap suit.

    Does anyone still remember why we got computers in the first place?

    • You misunderstand what I was saying, not that the Bob program transformed into what we now know as AR like the one Meta is designing.

      Rather that these metaphors were very present in 2000s Windows and Office programs, and were very successful in getting regular users to understand computers and bringing about the Personal Computer revolution.

    • > Does anyone still remember why we got computers in the first place?

      Uhhhh, to play videogames?

      (That was the Beavis 'n Butthead voice.)

  • Those predated Bob, by a long time.

    I remember encountering them in an old Xerox system, in the early 1980s.

    Bob was awful. However, I have to confess that I once tried designing UI like that, and learned painful lessons, in the process.

    • I'm interested in specifics if you remember them. What Xerox system, are we talking an Operating system? A mainframe? A computer + OS package? An office program?

      And what were the metaphors specifically, folders or cutting and pasting?

      Thanks.

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  • Those things were all totally standard and normal by the time Microsoft Bob came along

  • Those concepts were invented at Xerox PARC in the 1970s; certainly UNIX had them before MS windows, and "bob" was just a windows application anyway.

  • I think Bob was more (in)famous as the product which served as the origin story for Clippy in MS Office.