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.

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.

Source: PC Pro (blog)