Amusing timeline of Microsoft Windows adverts

If you’ve ever wondered how Windows was marketed through television from the mid-80s and onwards, then this bunch of YouTube clips will show you. Some are a little uninspiring, some are plain odd, and some are actually quite hilarious. Enjoy.

Windows 1.0

My favourite of the lot, simply because it’s got Microsoft CEO Steve Ballmer in it, and he scares me. I wonder if he was a used car salesman in another life...

Windows 2.x - 386

If you’re into mind-altering substances, then you’ll probably want to avoid this one, as it’ll probably have your head spinning for weeks. However, it’s worth watching just for the incredibly cool retro Gargoyles.

Windows 95

Kind of reminds me of an episode of Sesame Street. Not that I was still watching children’s programs at the age of 15… obviously.

Windows 98

There’s a bit of a spy theme to this one, if you hadn’t noticed. Well, Microsoft did later enlist the help of the NSA to tighten the security of Windows Vista after all.

Windows 2000

The fictitious prodigal son of Steve Ballmer features here. Highly amusing; especially the ‘hard sell’ scene in the office.

Windows XP

Microsoft used Madonna’s Ray of Light to promote Windows XP in this vid. It still ended up being a little cheesy though, but at least it did get the point across.