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Now vs. Then: A brief and incomplete history of Microsoft Windows

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For those of you who have watched Microsoft grow into the technology behemoth it is today, there may be certain parts of its history you fondly remember – and others you do not.

To be specific, Microsoft’s most famous product, Windows, has given us a whole host of tools and features, personalities and gimmicks, all designed to strengthen its brand. Some of them have worked. Some of them are best forgotten.

Well, not completely forgotten. To fully cover an incomplete history of anything, one must only recall the most entertaining or important parts. So below is a quintuplet of comparisons between the now and the then, the stories behind the products and the possibilities of its future.

It’s Microsoft, Now versus Then.

1. “We’re Facebook friends, but…he’s so chatty.”

Microsoft_ Body wrap_350x250px_op1Akin to an annoying Uncle whose friend request you instantly regretted accepting, Cortana digitally eye rolled at the mere mention of Clippit (see video, above) – affectionately known as Clippy, Microsoft’s oft-bemoaned paperclip help tool – when the AI was first launched.

Which makes sense: the generational, computing gap between Cortana and Clippy is stark. Clippy was more of a glorified help tool that popped up randomly when you were authoring documents with Office ’97. Fastforward two decades and advancements in AI has led to Cortana, a subtler, but all-knowing (and faceless) digital assistant that has been integrated into several Microsoft products, including Windows 10.

Intelligence to one side, it’s funny that all of Microsoft’s endeavours in this space – time, capital, resources – has been to rid itself of the infamy of Cortana’s annoying Uncle Clippy. And what does Cortana say now? Her tone has softened somewhat:

“Clippy’s enjoying his retirement, out of the media glare…he’s living his sunset years playing Bridge and winning.” Sweet.

2. User interface (UI) design is tailored to making things easy to find within any given interface, and boy, has Microsoft had a journey attempting that over the years.

From Windows 1 to 10, via Windows ME, XP and Vista, Microsoft has had some wins (and scored some own goals) over its evolution, but each time the company has tried to market a design that is both bold and intuitive to use.

Windows 1, released in 1985, relied on a lot of mouse control well before computer mice were commonplace. Windows 2 introduced the minimise and maximise functions two years later, while Windows 3 and 3.1 gave users multi-tasking options – and that classic computer black-hole, Minesweeper. Windows ’95 birthed the famous ‘Start’ button, and XP gave us all the visual overhaul the interface so desperately needed with its verdant green, Napa Valley, Vista (seriously, all that grey before got us, well, grey).

Despite that progress, Microsoft has done some U-turns in its history, like abandoning the ‘Start’ button, before reincarnating it for Windows 10, but it’s a good parable of the journey UI design has taken anyway. Maybe the brand hasn’t changed at its heart all that much.

3. Nothing gets Microsoft more excited than the prospect of tieing a band to a product launch, so here are our top five entries:

Weezer’s Buddy Holly video was included on the Windows 95 install CD well before Clean Bandit appeared in (widely hated) adverts for Windows mobile. Brian Elso got involved with Windows XP, Rolling Stones’ Start Me Up launched Windows ’95, and then-Friends’ stars Jennifer Anniston and Matthew Perry helped with their slogan “Could it be any more up-to-date?” (OK, so the last one isn’t a band, but we just had to slot it in somewhere…)

Special bonus: Someone’s made a YouTube video that plays Smashmouth’s All Star using only Windows XP error sounds.

4. Microsoft hasn’t been the only thing evolving over the years. As personal computer usages increased so too has the security threat landscape, forcing brands and businesses to continually reinforce its offerings.

Windows has almost been a victim of its own success: everyone has a Windows PC, which has made them attractive targets for attacks. Windows 8, for example, made substantial security updates since Windows 7, like the delivery of malware resistance (like secure and trusted boot), much improved data protection (trusted platform module 2.0, device encryption, support for encrypted hard drives), and modern access control (virtual smartcards, dynamic access control).

Security is a game that has no end.

5. Windows and its backgrounds come and go (here’s looking at you, random tulip fields) but nothing will be more iconic than Windows XP ‘Bliss’ desktop background image.

Remember the rolling green hills and blue sky? The story of how it came to be is an interesting one, involving a National Geographic photographer, Bill Gates, and one lazy afternoon in Napa Valley. The link also explains how you can travel to the site and be part of computing history.

So, now you know. A brief and incomplete history of Microsoft Windows can contain a whole menagerie of the global brands’ wins and works in progress, designs and characters, services and fancy AI bots. Part of Windows’ success lies within these, or, more specifically, in Microsoft’s ability to grow the brand alongside both the technology sector, and its users.

It has been able to gauge the appetite of trends and forecasts, implementing what they see and hear into the next iteration. It sometimes works well, and sometimes doesn’t. But that’s not necessarily a bad thing: many of Windows’ features looking back are pretty laughable to us now but that personality that has transcended into modern culture (hello Clippy). In this way, Windows has almost personified some features and humanised others them by allowing back stories to creep into common knowledge, like the Napa Valley photograph.

Of course, there are always serious angles to consider. Think about the recent WannaCry ransomware attack. Within 24 hours the worldwide cryptoworm affected 230,000 computers in 150 countries; security has morphed from an annual update which was passively regarded by the public to a front-of-mind, global issue which leads us handily to the rationale of incomplete histories anyway. Consumers adopt choice memory strategies, often forgetting the fun or ridiculous parts of an oft-used system like Windows because of darker current themes. This is where this little list helps; to remember, to compare, and to appreciate.


David Angwin

David Angwin

David is a leading spokesperson on cloud client-computing - which brings together desktop virtualization, thin and zero client computing, unified communications, mobility and cloud computing technology. With over 25 years’ experience in IT software, hardware and services he is able to speak with authority on desktop and mobile computing choices and their impact. David’s background includes technical and product management, bringing new solutions to market, as well as marketing and business management roles with US and UK-based high-tech companies.

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