Why Was Windows 95 Such a Big Deal?

It’s safe to say that those of us alive, and above the mental capacity of an 8 year old in the 90s witnessed something special. Never again will people absolutely flock en-masse and lose their absolute sh*t, just to get hold of an operating system. I mean, can you imagine that happening with Windows 11?

No, instead, we just have millions of people rapidly declining the upgrade whenever Microsoft try to force it upon us.

So why was Windows 95 such a big deal? Why was it the iPhone launch of its time? Well, to understand this we first have to understand what came before, starting with DOS. 86-DOS.

In April 1980, 24 year old Tim Paterson started developing an operating system he called QDOS (standing for Quick & Dirty Operating System). His company, Seattle Computer Products was one of the first to begin manufacturing computer systems based around the new 16-Bit Intel 8086 processor, but needed a functioning operating system to sell their products. At the time Digital Research were producing the industry standard OS, but CP/M was designed for 8-bit systems, and they were dragging their heels porting it across to the 8086; a somewhat costly mistake. By December 1980, QDOS had been renamed to 86-DOS, and Seattle Computer Products were able to sell it for $95 for owners of their hardware, or prospective buyers.

At around the same time IBM were developing a new Intel 8088 personal computer, and were also on the hunt for an operating system. They also turned to Digital Research, but Digital Research declined IBM’s proposal of $250,000 in exchange for unlimited distribution, instead wanting a royalty based model. IBM then went to Bill Gates, head of Microsoft, who had worked with Seattle Computer Products in the past, creating Microsoft BASIC for their systems.

In a somewhat sneaky deal, Gates went back to SCP to negotiate and purchase 86-DOS for $50,000, which after a few modifications was then licenced to IBM for use on their new Personal Computer. This became PC DOS 1.0 and shipped as standard with every IBM PC, with Microsoft still retaining the rights to sell it themselves under the MS-DOS brand, as they saw fit.

Now, IBM’s strategy of using off the shelf parts for their PC meant that the industry around their hardware grew rapidly, as did the uptake, which meant that those of using wanting, or needing to use a computer would likely have to embrace this once called Quick and Dirty Operating System, and therefore, it’s command line driven interface.

This, is pretty much all you get when you turn on a PC running DOS.

A drive label and a flashing prompt.

OK GOOD LUCK WITH THAT.

From this point, intuitiveness goes out the window. It was up to you to learn & understand exactly how to navigate your system. How to start programs. How to configure your memory. How to edit files. How to copy files. How to change your system configuration. All using text based commands.

Now, this wasn’t necessarily something new, after all, most computers of the era would throw you straight into a similar situation upon boot, but for those of us who weren’t hobbyists or enthusiasts. Perhaps, someone just using a computer for their job, this wasn’t the most user friendly situation.

This was something that a little company called Apple had the foresight to understand. Steve Jobs had many talents, but he was particularly good at turning something created by and for techheads into something that the masses could not only use, but actually, want to use.

Now, this is an Apple Mac. First released in 1984 and described as “revolutionary” by the New York Times, and for good reason. Rather than being a bulky system of components that would boot into a virtual abyss. The Macintosh would take users straight into an intuitive Graphical User Interface, controlled by a mouse, featuring a single button which was quicker to pick up than your mum on Burn’s Night.

But this wasn’t even the first machine with a GUI. It wasn’t even the first machine Apple had launched with a GUI. That machine was the Apple Lisa, launched in January 1983, with the graphical desktop idea actually nabbed from the Xerox Alto workstation that Jobs had seen during a 1979 visit to Xerox PARC.

Regardless of its origin, the world of computing now had two distinct paths. One, the clunky but popular IBM PC. The other, the smooth and finessed world of Graphical User Interfaces, spearheaded by Apple, but quickly followed by the likes of the Atari ST and Amiga.

Of course, the IBM PC wasn’t going to be left in the dark, literally. In fact, various developers had created GUIs to run on it, including Digital Research themselves, who launched their GEM Desktop Environment in February 1985. This allowed users to plug a mouse into their PCs serial port, and navigate their files using the same point and click action that Mac users were already basking in.

By this point, Microsoft had licenced their operating system to hundreds of other companies, and with hardware manufacturers creating clones of the IBM PC hardware, it had quickly overtaken IBM’s PC-DOS as the de-facto operating system.

In April 1985 MS-DOS 3.0 was launched, which significantly improved on previous versions, allowing among other things, support for networks and higher density floppy disks. But Microsoft weren’t blind to the world around them and had realised they needed to jump on the Graphical User Interface bandwagon as well, which they would do so with the launch of Microsoft Windows in November 1985, which was developed by a team led by Scott A. McGregor; the man behind Xerox PARC’s original windowing system.

Now, Windows 1 is a far cry from what we have today, Windows couldn’t be overlapped, and even compared to MacOS, it looked like a toddler’s fever dream, but for a lot of users, it changed how they interacted with their computer. Thanks to the inroads Microsoft had already made with Original Equipment Manufacturers and businesses alike, Windows could be distributed to more users and make more of an impact than other IBM PC Compatible GUIs had done so far. Despite that, it didn’t sell tremendously well.

In December 1987, Windows 2.0 was released, allowing access to expanded memory and shortly after, introducing a protected mode kernel, the ability to run MS-DOS programs in tandem under a “virtual 8086” CPU mode and the welcome addition of pre-emptive multitasking .

However, it was Windows 3.0, released in 1990 where the software really began to shine. Up until this point, most programs were still written for DOS. Sure, Windows was a nice to have, and it allowed you to keep everything organised and accessible, but with computing power being somewhat limited, the additional overheads created by the Graphical User Interface meant that DOS programs were faster, used less memory and just generally more compatible, given that other users didn’t always have a copy of Windows to open files with. It was also far more common for developers to create DOS software than Windows compatible software, given that almost very PC owner had DOS, but only a sub-set had Windows.

But by 1990, computers were getting faster. Not only had the 286 processor been out for several years, but many users now had a 386, offering SIGNIFICANT POWER over previous systems. Windows 3.0 then, would play into this, offering Virtual Memory which allowed the system to use hard drive space effectively as working memory.

Windows 3 also looked a hell of a lot better than previous versions, making use of that sexy VGA mode.

With Windows 3, Microsoft also started dabbling in large scale launch event. Hosted at the New York City Centre Theatre with 6,000 attendees, it was also broadcast across North America is various Microsoft social fairs. Spending $3million on these events, Bill Gates labelled it the “most extravagant, extensive, and expensive software introduction ever”. The idea with Windows 3 was it make it more appealing to the public, given that previous versions were seem more as a business tool, and the plan started to work, with more OEM manufacturers including the Operating Environment out of the box.

This then, was the first version of Windows to achieve commercial success outside of Microsoft’s traditional supply routes, and this demand led to a slew of programs being developed to run inside the Windows framework. It also shook up Microsoft’s direction and marketing methods.

However, regardless of which version you had, DOS was always the master here. Your PC always had to boot to DOS, after all, it ran on DOS. This wasn’t Windows’ fault, it’s just the world it was born into. Windows was simply a program that you called from DOS, it was a shell that ran on top, and that’s all it could ever be. Sure it had some fancy schmancy features, but it was ultimately just a DOS program that made your life a little easier, which not only meant that it was limited by the constraints of DOS, but also, if you wanted to run anything resource intensive, then quitting to DOS was really the only way to go. Given the extra layers of abstraction Windows added between a program and the system hardware, the overheads for your average PC at the time were just too great, and that’s even before tackling the frequent resource and application errors that Windows would throw.

In June 1991, Microsoft would launch MS-DOS 5.0

A significant upgrade over previous DOS versions, and the first which allowed you to upgrade your current DOS version. Because of this, Microsoft also chose to do a slightly bigger marketing campaign than they had in the past. At the time Brad Chase was in charge of the launch; Chase originally joining Microsoft as the product manager for Microsoft Works & Office on the Macintosh. Having gained experience running promotions for Apple, he elected to add a bit of spice to this campaign¹. This was a two pronged attack of firstly, visiting user groups to disseminate and explain the new features, and secondly, pushing the new upgrade with TV advertising, print and holding a launch event on a large boat in New York with Dave Brubeck performing his song “Take Five”. This launch worked so well that in some stores, people were actually queuing up at midnight the night before launch.

But by April 1992, Bill Gates knew that PC users needed more, demanded more in fact. Although they had just released Windows 3.1, it was already lagging behind. Microsoft not only had competition from other platforms, it also had competition from its old partner, IBM, who had just released OS/2 2.0. An Operating System Microsoft had actually been helping write until Windows 3 took off. But also now, an operating system one step ahead of the traditional DOS and Windows combination, featuring a 32-bit API for native programs and the ability to run DOS software.

Rather than just providing an environment to run Windowed programs, the OS/2 Workplace Shell provided an environment for users to manage programs, files and devices intuitively. It was marketed by IBM as “a better DOS than DOS and a better Windows than Windows”, which it indeed, was.

Despite their huge market advantage, Bill Gates realised that if Microsoft didn’t keep up with the times, then the future of PC operating systems could easily fall into someone else’s hands, at a time when the stakes were highest. With this, two projects were initiated. One codenamed “Razzle”, and actually based around the OS/2 framework Microsoft had helped develop would be launched in July 1993 as Windows NT 3.1; offering similar advantages to OS/2 and aimed at high-end professional and server markets. The other was initially coined Win93; designed to be the next significant upgrade for the everyday user and one that needed to beat the balls off everything else, with a penned release date of June 1993.

On 5th March 1992, an email from Senior Vice President and Project Lead Brad Silverberg, stated “Our mission is to deliver systems software for high-volume platforms, i.e., personal systems. This means that ongoing major investments will be for low-end desktops, notebooks, portable machines, pens, etc.

Win93 will focus on usability, especially the shell. Ours is rather long in the tooth and we know we need improvements. This is our chance to do something cool. There are a number of other subgoals for Win93. One of which is to make Windows a lot more functional too, for things today you have to drop down to MS-DOS to accomplish. Everything you can do from DOS should be available from Windows”²

And this is key. Everything you can do from DOS should be available from Windows. Because Microsoft weren’t just producers of Operating Systems. They were producers of software, and within DOS the likes of Microsoft Office was already in a fierce competition with products like Lotus 1-2-3 and Word Perfect. Big players in the world of business. We’ll come back to that later.

But by 1994 Windows hadn’t really advanced much further, other than incremental updates on the existing product. We were now on version 3.11. Windows for Workgroups… woooowwwwww. But things were heating up. This was now a time when PC’s weren’t just prevalent in America; even your average UK household would probably have a PC in the corner, on one of these desks, with a dot matrix, or even bubble jet, if you were lucky, printer, stowed safely underneath. Plus, there was a little thing called the Internet that people were just starting to get excited about.

In that time IBM had released two significant releases of OS/2, with OS/2 Warp 3 their latest, and greatest offering. Whilst Apple were about to launch Mac OS 7.5, introducing the Apple Guide, the Control Strip and various methods for customising the desktop.

Win93 then, was running behind, and that’s mainly due to the design changes made along the way. Initially, it was developed to go hand-in-hand with 32-Bit subsystems Project Panther & Cougar, along with Jaguar; essentially DOS 7. But it was felt that the whole concept of a separate command line driven operating system was getting too long in the tooth, and all of these projects were bundled under the heading of Project “Chicago”; as a wholly integrated graphical Operating System.

“As the successor to Microsoft MS-DOS, Windows 3.1 and Windows for Workgroups 3.11, Windows “Chicago” is the next major release of the standard operating system for the desktop and portable PC. There is something for everyone, whether it’s a more intuitive way to work, new capabilities like “surfing the information highway,” or better support for managing a 1,000 PC installation site.”

This is the blurb at the top of the review guide handed out with preview copies of the then named Windows Chicago³, along with its main selling points;

“Chicago makes PCs even easier to use”

“Chicago is faster and more powerful operating system”

“Chicago integrates network connectivity and manageability”

Sounds like some pretty sensible and straight-forward improvements, right? So how did we get from this….. TO THIS???

Well, there lies the brilliance of the Microsoft marketing team at this time, who played every angle, pretty perfectly.

Marketing to Perfection

Before this point Microsoft’s strategy for new products was *silence*. Everything was hush hush, everything was top secret. Which led to speculation, and it led to anticipation, but it didn’t lead to many column inches; after all, there was nothing to write home about. It was actually Brad Chase, the marketing lead for Windows 95 who made the call that actually, it was time to turn that upside down and tell the world EVERYTHING they could, in a bid to not just alleviate any fears people had about this weird world of computing, but also to get other companies producing software and accessories, themselves then adding to the hyperbole.

Brad had two goals with the marketing campaign, the first was to “bring computers into the mainstream”, and the second being to make the product “a consumer phenomenon”¹. Two goals which actually were perfectly aligned with what the new OS hoped to be.

Brad named this strategy “The E-Strategy”, Educate, Excite and Engage, for obvious reasons (6 mins Podcast)⁴, and as part of this strategy, the other Brad, Brad Silverberg, decided to put Chicago through the largest Beta test to date, which resulted in 400,000 people taking part. Part of which was the preview program, which cost users $30 to get a sneak peek of the upcoming OS. So in this way, Microsoft not only got paid for most of their bugs to be ironed out, but also, the press treadmill began a good year in advance.

By September 1994, the press had a name. Windows 95, and the information was flowing.

“We do want people to move forward, just as we wanted people to move from 3.0 to 3.1” says Brad Struss…. Good lord how many Brad’s worked in this company??

Software was already beginning to label itself “Windows 95 Ready” and discussions around 32 bit API calls were there to whet the appetites of anyone concerned.

And before 1994 was out, there was already a slew of multimedia experiences, videos and books claiming to know the full details of this revolutionary new Operating System, most of which focussed on the iconic “Start” button to lure people in. After all, this single button would be the gateway to, well, everything.

Most of this press would be concentrated around how much simpler Windows 95 made the PC to use, along with how much more stable it will be, with lots of talk about how the very limiting and user unfriendly DOS would be pushed aside entirely. In reality, DOS wasn’t discarded, but it was hidden-away, designed to run underneath Windows, just like prior versions, but in a fashion where a regular user just wouldn’t see or experience it. This was for a number of reasons, including development time, but chiefly, it allowed backwards compatibility with a lot of existing 16 bit software. Add to this the new Plug & Play system that meant peripherals could -in theory- just be plugged in and they’d be good to go, alongside a variety of improvements, and it felt like 95 would be streets ahead of anything prior, in the world of PCs anyway.

In reality, this was the same thing Steve Jobs and Apple had done years prior, but now Microsoft were doing it with the mass market already in their hands.

Microsoft had initially touted the Spring of 95 as the launch window, however this came and went, but the press didn’t seem to tire, in fact, they just got more and more hyped about it. Thanks in part to the “E-Strategy”. Borrowing from their DOS 5 launch, Microsoft had dedicated teams working directly to educate, excite and engage business customers, OEM computer manufacturers, third party developers and the press ¹. But absolutely key was engaging home users; after all, that demand alone would enthuse everyone else. Although DOS 5 had regions were people were queuing from midnight, this needed to be replicated around the world in every major city.

To aid with this Microsoft launched a series of promos and collaborations leading up to the launch, including a Windows 95 Sapporo Black Label beer over in Japan;

The campaign culminated in a VHS called “Microsoft Windows 95 Video Guide”. Now, unless you’ve been living under a rock, this is no news to you, even in 2025.

Featuring Matthew Perry alongside Jennifer Aniston, and written by Seinfeld contributor “Jonathan Gross”, this was definitely something to remember…. or not, depending on your perspective.

With Windows 95 having been released to manufacturing on July 14th 1995, for English languages, the retail launch date was now set for August 24th 1995, with other languages following shortly after.

By this point, Microsoft had people were coming to them, asking if they could help promote the product. Wanting to be part of the hype. Brad recounts when Don King phoned him up to try and get Windows 95 into boxing matches… (26 minutes), along with Steven Spielberg who wanted to pitch in on the marketing campaign.

But it was Doonesbury running a week long series of comic strips making fun of Windows 95, that really solidified things for Brad. He recounts telling his team that they had reached their goals, when a week before launch because of it. And indeed, they had, because the midnight queues they were hoping for were absolutely rife, launching around the globe at midnight 24th August 1995, with the initial queues seen in New Zealand synonymous with what followed.

But things were just getting started…

As eager punters were already at home, frantically installing their new operating system, The Microsoft campus in Redmond, Washington State, was gearing up for a launch circus the likes of which the world has never seen. Now I feel like this is something we need to work through, step by step, to really take in the sensational disregard for dignity that was on display here.

Details of the event were mostly spread online, which at the time, was a pretty impressive feat. But it’s no shock to say that 2000 guests attended⁵, along with 500 members of the press, magazine writers and various “tech celebs” of the time, including Lance Ulanoff of PC Magazine, who recalls getting bused to the campus, weaving through a series of greeting tents, before being marched into the presentation pavilion where Bill Gates took the stage.

In an article on medium.com he reports there being “palpable excitement that day, which appeared tailor-made for the launch”⁶.

After several Developer Stories, the audience were introduced the the real star of the show, That Iconic Start Button, before Jay Leno took comedic duties alongside Bill, who talked everyone through the glory of Windows 95.

After various questionable jokes, the introduction of Windows 95 desktop, remembering that this was a brand new thing for Windows, the back of the stage gave way to reveal swathes of developers dressed in Windows logo coloured attire and that iconic Stones track played for the first time; Start it Up from their 1981 album Tattoo You.

The famously shared and heralded video that looks like it’s extracted directly from a Junior School disco featuring Steve Balmer, Gates, et-all dancing on stage, is actually from a different event, although still linked to the Windows 95 launch.

But this was a huge party, filled with the entire Windows team, press, third party developers and anyone else who was important enough to get a goodie bag filled with Windows 95 merchandise and a portable CD player.

Although the internet wasn’t geared up for streaming yet, there was an online version of this event so that everyone could feel part of the hype.

However, events were happening around the world. In New York, the Empire State Building was lit to match the Windows logo colours.

In Toronto, a 100m banner was draped over the CN Tower, and in the UK, a launch event at London’s Equinox Nightclub in Leicester Square hosted by Jonathan Ross was attended by a star-studded cast. Fake… star-studded cast, I might add. But in fairness, they were very good look-a-likes. After Gates’ 5 minute video appearance, Ross quipped, “money can buy you lots of things, but it does not necessarily buy you a decent haircut”⁷.

Alongside this, giant versions of the Windows 95 logo were painted in fields, probably why Aliens stopped making crop circles, and Microsoft paid for 1.5million copies of The Times to be distributed freely, twice its usual distribution number, all with front page press covering the launch. Whilst over in Sydney, Dame Edna Everage unveiled the new OS, as one of 20 events carried out across the country.

Over in Eastern Europe, things were a little more, well Eastern European, with pirated copies having been sold for the past few months, and any excitement… well there was no excitement.

Time to Roll some Stones

But as the reports of Microsoft’s event appeared around the globe, so did their new advertising campaign, a campaign that’s often used as a yardstick for promotion done right. It was the ad agency Wieden+Kennedy who had come up with the idea, although they elected to leave the negotiation to Brad Chase, who was flown out to meet their promoter, Michael Cohl, at the Paradiso in Amsterdam, where the Stones were about to perform two unplugged concerts. Despite reports from The Sun that the deal cost Microsoft $14million, the Stones had originally requested $12million, before a tonne of negotiation got it down to a rumoured $3million. Apparently with Jagger unhappy with the deal, but because Richards wanted the money, it was sealed.

Which really was great for both sides, it opened the Stones up for various future deals, and it meant that Micrsoft didn’t have to fall onto their backup advertising plan, which would have made nowhere near the impact that Start me up did, with Wieden+Kennedy, along with Cynthia Krass, the head of Windows 95 advertising, working overtime to shoot footage of an entire cross section of the population, to reflect the everyday folks they were targeting. The core message being that Windows 95 would “enable users to do new things and easily handle tasks that were previously difficult”⁸.

This combination of good communication, a good product, a good message, good celebrities, a good song and importantly, a good budget helped Microsoft achieve the sales they wanted, with one million copies of the operating shipped worldwide in just four days.

Although IBM stuck to their guns, insisting on trying to ship OS/2 Warp with their computers, they finally conceded 15 minutes before the launch event, signing a contract that would allow Windows 95 to be pre-installed on their machines. However, coming this late to the party badly impacted their sales. With customers choosing to buy new PCs from day one, with 95 already installed.

Windows 95 achieved dominance really before the launch party was even finished.

With an initial rumoured spend of some $300million, the total marketing spend for Windows 95 would eventually be estimated at $1billion. Not that it mattered, given the sales figures. By 1998, Windows 95 had a 57.% marketshare, with their latest product Windows 98, taking 17%. Obtaining absolute dominance in a way that only Bill Gates, unimpeded by legalities, could.

As Brad Chase stated in a recent podcast, “You can’t market your way out of a bad product in the software industry, but you can take a great product and make it even more fantastic”¹, so although we might look back on Windows 95 as being a little shoddy, a little rough around the edges. It’s fair to say that it wasn’t totally bad. It did what it set out to do, it shook up the market, it brought us out of the DOS age, and it actually did make computers, on the whole, a lot easier to use. All the marketing did was turn a good product, into a good product that everyone wanted, at a time when computers were really just starting to get exciting. A culmination of marketing, timing and product, that educated, excited and engaged.

You know, I often find it hard to work out whether it was my age, naivety, ignorance or the fact it was just a simpler time, but I often feel like some of these 90s events, like the launch of Windows 95 felt monumental, like it was going to change the world, like we were getting to that glorious vision of the future faster than ever, and looking back it just feels calming. Maybe it’s just a rose tinted nostalgia, but in reality, Windows 95 did do to computers what later the Wii would do to gaming, and what Apple did for mobile phones, and so really, regardless, it was fun, and maybe that’s all that matters.

For third party companies however, it wasn’t all rosy…

Remember that Microsoft were struggling with competition to their business products? Well, by moving everyone across to a new Windows platform. It kinda killed the DOS based competition, and meant businesses upgraded to new office suites. Suites that Microsoft had ready before launch day, and designed to make the most of their new environment.

This was not only the case with their Office suite, but by having the Microsoft Network ready to go on very copy of Windows, it also dealt a massive blow to internet providers, who had to resort to cover discs, and huge promotions to get users to install their internet connection suites on top of the new operating system.

In the build up to the launch, and the days proceeding it, this increasingly became a issue, with competitors all jumping on their boxes to complain. Something that they would kinda pay for at a later date, although by this point, it didn’t really matter.

Microsoft had pulled a blinder. Not just achieving incredible sales, but by ensuring their future through all the software which ran on top.

Remember this video of Bill Gates jumping the chair?… “I’ll cheat a little bit”…. Yeah, turns out that’s really his business approach too, which fair play to the man.

He not only jumped the chair, but everyone else too.

Until next time, I’ve been Nostalgia Nerd Toodleoo.

1. adventofcomputing.libsyn.com/episode-335-brad-chase-interview-marketing-lead-for-windows-95-and-much-more [↩] [↩] [↩] [↩]
2. web.archive.org/web/20230322224425/http://groklaw.net/pdf/iowa/www.iowaconsumercase.org/011607/1000/PX01263.pdf [↩]
3. www.tech-insider.org/windows/research/acrobat/940601.pdf [↩]
4. www.microsoftalumni.com/s/1769/19/interior.aspx?sid=1769&gid=2&pgid=2306&sitebuilder=1&contentbuilder=1 [↩]
5. www.newspapers.com/image/123023253/?match=1&terms=windows%2095%20launch%20london [↩]
6. onezero.medium.com/remembering-the-iconic-windows-95-launch-94cfcf215d50 [↩]
7. www.newspapers.com/image/261169438/?match=1&terms=windows%2095%20equinox%20nightclub [↩]
8. www.bradchase.net/startmeup [↩]