As We Wait for Windows 10... A History of Windows Through TV Adverts

By James O Malley on at

Windows 10 will finally be available in a matter of days. What that means is we're on the cusp of an inevitable big marketing campaign for the new operating system. So perhaps it is as good a time as any to instead take a look back on Windows adverts from years gone by. Not just reminisce about simpler times, or get nostalgic about a time when anthropomorphic paperclips were treated with score, but also to ask "WTF were they thinking?" Here's a run down of some of the best and weirdest adverts.

Windows 1.9

So what did Windows 1.0 have going for it back in 1985? Why you don't you ask former Microsoft CEO Steve Ballmer in the days before he took the top job? Check out this extraordinary advert in which someone thought making him look like a dodgy car salesman was a good way to build trust. If only all Microsoft adverts were done like this.

Sadly there doesn't appear to be any commercials for Windows 2.0, so you'll just have to imagine what Steve Ballmer might have got up to on his next adventure.

Windows 3/3.1/3.11

Windows 3 was launched with a harrowing tale of how computers are destroying the jobs of the elderly, in an advert that sees a secretary confused about why her old typewriter has been replaced by a computer. It's a perfect example of the sort of advert you remember being fine, but that they probably wouldn't get away with making today. The joke at the end is pretty good too.

You know what they say, anything we can do, Japan can do but crazier. As they prove in this utterly bewildering advert for Windows 3.

Windows 95

Windows 95 was when computers stopped being for nerds, and became something that normal people might own too. Our favourite thing about this weird advert Windows 95 advert is what we assume must be an internet cafe from the '90s, which looks like a coffee shop but with a massive, clunking, desktop PC on the table.

Microsoft also made this ten minute monstrosity going through some of the new features and an incredibly ropey looking spaceship flying game of some sort...

Oh, and then there's this. You might have seen this clip before, in which Jennifer Aniston and Matthew Perry from Friends star in a video showing off the new features found in Windows 95. It went viral a few months ago, with commentators calling it the most '90s thing ever... and, well, they're not wrong.

And finally, check out this advert from Apple, which was keen to point out that its '90s machines could dual boot with Windows 95.

Windows 98

Windows 98 was a good year for Microsoft adverts. Check out this whizzy attempt at making an operating system seem exciting.

Unexpectedly there are also a surprising number of "parodies" of this advert on YouTube, where it has been recreated using other operating systems.

This isn't advertising Windows 98, but is from the Windows 98 era. Check out this commercial for Microsoft's mouse line. The best bit is clearly hearing how the person who wrote the advert is struggling to think of interesting things to say about the nearly identical line of mice:

Windows ME

Windows ME, which was released in 2000 was widely criticised for being a bit terrible. However bad the OS was, the TV advert was worse. While using a computer might be exciting, making watching someone use a computer look exciting is even trickier, as this advert is testament to.

Amusingly, one of the close-ups in the ad focuses on the System Restore, in spite of the fact that one of the major criticisms of the OS was the broken Restore functionality that mis-dated snapshots... which as you might imagine, caused some problems.

Windows XP

Windows XP came out in 2001 and fixed many of the horrible flaws in Windows ME. The adverts were getting more like modern tech adverts too, with less focus on functionality and more on playing music and showing the lifestyle of the people who they want to use the product.

The best advert though once again starred Steve Ballmer, who reprised his role from the Windows 1.0 advert to bring it up to date.

Sadly it doesn't seem like he'll be doing another turn for Windows 10, as we can't imagine he was too happy about being turfed out as CEO and replaced by Satya Nadella.

Office XP also had some weird adverts made for it, like this one, which you might not want to watch if you're reading this sat in the middle of an open-plan office.

Windows Vista

"The Wow Starts Now" claimed Microsoft back in 2009. That must have been as in "Wow, I can't believe how bad that operating system is", as Vista was quickly replaced by Windows 7 only two years later. Vista was bloated, slow, and demanded big (for the time) system requirements to run correctly; consequently, the OS struggled on lower powered machines.

It also removed tonnes of features that were present in XP. Here's how Microsoft polished that particular turd:

Conversely though, Vista also sparked some of the best adverts to date. Check out these bizarre clips featuring Bill Gates and comedian Jerry Seinfeld as they attempt to buy shoes and live with a normal family:

As many people's frustrations with Vista boiled over (to the extent that PC manufacturers started offering XP downgrades) Apple also chipped in with the following variation on its famous "Mac vs PC" adverts (the UK version of these ads featured Mitchell and Webb). It was a little more hostile than the company's earlier ads targeted at PC users.

And finally, while not strictly an advert we couldn't resist sharing this clip showing Windows 95 blowing away the old Windows 3.1. We can't help but think that there could be a Windows 10 remake of this with Windows 8 turning to dust. It even adds a Start button, just like Windows 95 did.

Windows 7

For Windows 7 Microsoft took things back to basics with its "I'm a PC" campaign which saw normal users explain new features on the premise that the OS was informed by feedback from users who had been horrified by Vista.

The launch wasn't all this slick though. Again, this isn't strictly a commercial, but one of Microsoft's launch activities was to encourage people to host "Windows 7 Parties" to show off the new features. And to support it, this utterly unbearable video was made with some actors telling people how to do it. Try not to claw your face off in embarrassment:

Apple also responded to the Windows 7 launch with this sick-burn following up on earlier adverts:

Windows 8

And finally, as we wait for Windows 10... what about Windows 8? 8 Launched in 2012, which is perhaps a little for ironic distance (their crazy hair and clothes still look pretty sensible in 2015). So what was there? There was fairly conventional adverts like this:

But we prefer this slightly crazier advert explaining how Windows 8 is both beautiful and fast.

Just nobody ask where the Start button is.

So what can we expect from Windows 10? We're just hoping they somehow figure out how to bring back Ballmer.