CNET has a great article on the worst Microsoft promotional videos ever. Cheesy doesn't quite describe what can only be called Microsoft's worst moment. Forget all those antitrust lawsuits, how much Vista sucked, or those RRoDs the 360 keeps getting. This is just horrible.
And funny. Ridiculously funny.

Damn, microsoft just keeps outdoing itself with crappier and crappier ad campaigns. : )

Fan-frigging-tastic.

MS-DOS rap for the goddamn win.

I think the windows 7 ones were the worst. The old stuff is just awesome :P

Only because they're riding the nostalgia train by now.

Anything that showed the MSN "Butterfly".
Ironic that they chose a bug to represent their brand.

Their old slogan (before they went brand schizophrenic and turned half of their services into Live while keeping MSN.com) was More Useful Everyday. Which is ironic, considering their site is a freaking mess.

I remember an ad they had that idiot in, for their messenger program. This was only a few years ago, and they were acting like having emoticons in their program was some sort of never-before-seen feature.
Similarly, there were ads for AOL broadband many years ago touting the fact that the phone could be used at the same time, but worded it to imply that it was some special feature.

The 386 one was just stunning. LOL
As were the glaring problems with the Windows 7 ones. Magical disappearing laptops, Batman! Gotta wonder what the logic behind the blatant Sony ad was too.

I guess I'm the odd one, I never had much problems with vista, there only was a few DOS-legacy games that I couldn't get to work. As for the add campaign, MS has definately jumped the shark... Insert Fonzy sound effect here.

I think anything that gets Steve Ballmer out of his cage is hilarious.

huh?

You're probably on Windows 7, so you don't care.

Then I think you'll enjoy this.
http://www.youtube.com/watch?v=8zEQhhaJsU4