“Many a small thing has been made large by the right kind of advertising” – Mark Twain

Microsoft wouldn’t be where it is today without the ability to capture the imagination of its customers with advertising. But when Microsoft’s ad machine misfires it does so dramatically, as the following selection of clips from the last decade will show.

Despite its po-faced image – something that Apple’s I’m a Mac adverts sought to perpetuate – Microsoft hasn’t always taken itself so seriously. Delve back into the mists and you’ll find this gem from Steve Ballmer – a perfect example of a large thing being made even larger by the right kind of advertising. Over to you, 1986 Steve.

In the early days downright zaniness was a key part of Microsoft’s marketing appeal, with even videos sent to its own retailers delighting in juxtaposing the perceived seriousness of the brand with the downright bizarre. Take the next clip. A seemingly innocuous marketing video at first glance, it’s not until you hit the seven-minute mark that things take a turn for the exceedingly strange.

Fast forward to the year 2008 and Microsoft had clearly decided that even mentioning the product it was advertising was utterly passé. This time Bill Gates takes centre stage with renowned funny guy, Jerry Seinfeld. If the painfully stilted interplay between Gates and Seinfeld isn’t horrific enough – Gates looks like he’s delivering his lines with the help of a cattle prod – the final moments are about as gut-wrenchingly sickening as watching your dad try to do the Rolex Sweep after one too many Xmas ales. No, Bill. Please. Don’t wiggle like that. Ever. Again.

Yes it’s terrible, but Microsoft’s never met a dead horse it didn’t enjoy flogging. Cue another pair of adverts, this time placing Gates and Seinfeld in the midst of a “normal” family. Imagine Larry David’s Curb your Enthusiasm bleached of all its humour – yes, every last drop of it – and you’re halfway there. Thankfully, this was to be the last video from the duo, and it was to the deafening sound of utter indifference that Microsoft canned any further ads in the series. And, if you thought Gates’ arthritic gyrations at the end of the Shoe Circus were bad, wait for the Robot dance. Dear God.

It came as little surprise that even the creators of Family Guy struggled to mine the non-existent seam of comedy that was Windows 7 in the following clips. My favourite is the surreal side swipe at Apple’s spinning wheel of death, but the other two adverts appear to have had every ounce of humour ripped out by nervous marketing execs, their trousers worn thin from shuffling around in their seats. All it would have taken was a scene with Quagmire, his inimitable catchphrase and a reference to his doubtlessly illicit surfing habits, and Microsoft might just have had some irreverent comedy gold on their hands. Sadly, it wasn’t to be.

The worst was yet to come. Windows 7 needed to launch with a bang, and to accomplish this Microsoft’s hive mind somehow settled on the idea of a Windows 7 Party. The idea was simple in every sense of the word. Invite your friends to sit around eulogising about the wonders of Windows 7, and try to have a good time while you’re at it. But like an F1 key for social inadequates, or just disinterested sadists, Microsoft employed several actors, replete with rictus grins and the ability to laugh at the most inopportune moments, to show you just how to get that party started.

Just so you know, if you make it past the thirty second mark, your will is strong. If you make it to the end you’re probably in possession of superhuman powers and should consider using them to save the universe. Either that, or you’re dead. Come back, Bill; come back, Jerry, all is forgiven.

However, while the Windows 7 Party advert left us tearing at our retinas with a rusty biro, some of the year’s adverts from the big M have proved genuinely funny. Internet Explorer 8 may seem the most unlikely of targets for a genuinely amusing campaign, but the combination of Dean Cain of the New Adventures of Superman fame and some bizarre acronyms proved a winning combination.

Ironically enough, the funniest Microsoft-related videos had nothing to do with advertising at all, but were intended as a bit of light relief for new Microsoft employees. Made back in 2004, and allegedly leaked a few years later, they featured the winning partnership of Ricky Gervais and Stephen Merchant. With Gervais reprising his David Brent role, and Merchant taking on that of a Microsoft employee, the videos are enough to make us wish Bill and Jerry had left the ads to the experts.