Microsoft Bob: Microsoft's biggest flop of the 1990s
176 comments
·January 12, 2025TowerTall
alt227
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?!
robertlagrant
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.
alt227
I disagree. Metro UI was ugly, space wasting, and a blight on UI design. I even disliked it on mobile which it was arguably designed for.
slightwinder
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.
alt227
I dont see Apple or Google using room based interfaces, it seems to just be Microsoft these days.
Please can you point out some games that do this? I cant find any.
xerox13ster
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.
MadnessASAP
And Jesus wept!
internet_points
That video is 100% accurate of the feeling of VR in the 90's, both of the behaviour of the believers, the experience itself, and the reactions from the onlookers :)
causality0
I remember once buying a graphics card that included one of these virtual environments where files were on shelves, etc. Wish I could remember its name.
null
datavirtue
Magellan was pretty cool. I think it shipped on Magnavox PCs in the 386 era.
boomboomsubban
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.
anonymousiam
Melinda gates was more than just the product's marketing manager, she was in charge of the whole project.
https://www.cnbc.com/2017/11/29/the-lesson-melinda-gates-lea...
cr125rider
Wait wait wait, Comic Sans was born in Microsoft Bob!? Way to bury the lead! That’s an incredible little origin story!
LeoPanthera
According to Wikipedia, it was intended for Bob, but wasn't actually used in it, and ultimately first appeared in "3D Movie Maker".
edgineer
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.
kevinventullo
Yes, I have only positive memories of it! Customizing the house was like a primitive version of The Sims.
silisili
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.
ciabattabread
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).
asveikau
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.
narrator
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.
egil
My father installed it on our family mac. I somehow discovered that by quickly rebooting twice, it would start the usual Finder shell instead, albeit in English instead of the configured Norwegian. Fun times.
pjerem
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.
TimTheTinker
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.
phito
You just unlocked a core memory for me. I remember that house so well but haven't thought of it in decades!
cr125rider
“Adult Password” vs the much more common modern “Admin Password” is excellent
skeeter2020
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)
cr125rider
Petey the green bird, then gorilla was my buddy. Bonsai Buddy I think he was called!?
silisili
Ugh, I had forgotten all about that. I'll never get that creepy robotic "Day, z. Day, z" out of my head.
crazygringo
> 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...
sillywalk
> This feels like an urban legend made up after the fact.
Raymond Chen of Microsoft has this to say about that:
"... [the person adding 30 megs of random crap] could have just called the CryptGenRandom function to generate 30 megabytes of cryptographically random bytes, but where's the fun in that? Instead, he dug through the archives and found a copy of Microsoft Bob. He took all the floppy disk images and combined them into one big file. The contents of the Microsoft Bob floppy disk images are not particularly random, so he decided to scramble up the data by encrypting it. When it came time to enter the encryption key, he just smashed his hand haphazardly across the keyboard and out came an encrypted copy of Microsoft Bob. That's what went into the unused space as ballast data on the Windows XP CD..."[0]
[0] https://learn.microsoft.com/en-us/previous-versions/technet-...
LeoPanthera
I really want this to be true, but Bob came on six floppy disks, far less than 30M.
null
miffy900
It's entirely possible the disk images were just duplicated multiple times to get to 30M.
Mountain_Skies
It was added by David Plummer, who explains how and why he did it.
rasz
On the other hand guy has history of lying and scamming the public https://www.atg.wa.gov/news/news-releases/attorney-general-s...
dpierce9
Is this why there was a copy of Weezer’s Buddy Holly music video was on there too?
selcuka
> It would be way easier to just generate random bytes, and nobody could ever tell the difference.
Programmers love easter eggs.
Edit: sillywalk's comment proves my point.
Double_a_92
Without knowing the encryption key, it is just random data though. And since not even the creator knows, there sadly is no easter egg.
selcuka
Isn't it still an easter egg though? Just one that is very hard to find.
blackeyeblitzar
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.
ok123456
It gave us Comic Sans, which had a notable impact on culture. I wouldn't call that a flop.
duskwuff
Comic Sans was from Microsoft Comic Chat [1], which was a separate product from Bob.
breadwinner
Unlikely. Comic Chat project was not a high-budget project that could design its own font. Bob on the the other hand was, and according to Wikipedia did fund the development of Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans
gjsman-1000
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.
p_ing
It was a shell atop of Windows 3.x on a FAT16-formatted drive. Like 9x, the user account was only for personalization, not security.
null
notnaut
What?? What was the point, even?
wongarsu
Anyone can get in, but nobody can get in without leaving evidence behind.
tiahura
So you knew your kids had been doing something they shouldn't.
ok123456
It was meant to personalize settings on the family computer, not be Orange Book compliant.
chgs
To get people used to passwords
gazchop
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.
Loughla
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.
PeterHolzwarth
I believe it's a fairly popular font with dyslexics as well.
alexjplant
My mother was an early childhood teacher for decades and used it in everything she printed for her classes. I asked her why and she said it bore the closest resemblance to proper block print out of all the fonts available. I went through several bouts of unnecessary glyph modifications in my own handwriting when I was a kid because I thought various fonts looked cool so maybe there's something to it.
Personally I don't get the outrage. In my opinion the likes of Bradley Hand ITC and Papyrus are abused more often but nobody's ever accused me of having good taste ¯\_(ツ)_/¯
breadwinner
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.
FiddlerClamp
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.
giantrobot
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.
senderista
> 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.
breadwinner
> 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.
boulos
The Seattle / UW related branch of MSR definitely had a few wins in the graphics department.
As https://www.microsoft.com/en-us/research/blog/meteoric-rise-... reminded me, they were on like 20% of the SIGGRAPH papers in 1996. And several have stood the test of time, like Hugues's Progressive Meshes paper (https://dl.acm.org/doi/10.1145/237170.237216). A little later, the spherical harmonics paper (https://dl.acm.org/doi/10.1145/566570.566612) was basically all MSR (I think Jan maybe interned there while at MPI? It's been a long time...).
That isn't to defend anything in AI, but it's not the case that they had no impact. The oral history thing there claims that the first grammar checking in Office 97 came from their NLP work.
senderista
Off the top of my head: differential privacy (which is now being deployed at scale), differential dataflow (Materialize), shared logs (Corfu/Tango, productized by VMWare). I'm sure there's many more that would be easy to google.
null
jen20
> In my opinion nothing notable has ever come out of MSR, regardless of campus.
One notable thing that came out of the Cambridge (England) campus was the implementation of generics in the CLR.
kristopolous
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
1123581321
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.
Kwpolska
How did blogspam with zero screenshots get upvoted? Actually seeing the product helps understand why it flopped.
Karellen
The light-grey text on white background really enhances the vibe of the piece, too
dankwizard
"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.
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...