Microsoft's 9 All-Time Worst Ads

Microsoft's about to embark on a one billion dollar marketing adventure to support Kinect and Windows Phone 7. Good luck to them! Because as these past epically failed advertising efforts show, Microsoft could be about to waste a lotta of money if they're not careful with the creative:

Ballmer Sells Windows 1.0

You may not have realized it, but the terrible Microsoft advertising tradition goes all the way back to a young (though still bald and yelly) Steve Ballmer, doing his best used car salesman bit to push Windows 1.0 on an unsuspecting public.

Windows 386 Terrifying Rap

Okay, so this wasn't a TV ad. It was originally a 12-minute promotional video for Windows 386 that Microsoft sent out to retailers in 1988. The whole thing is a bizarre office drama, but the only part you need to worry about is this rapping banshee that will haunt your dreams forever, the end.

Windows 95 Promo Tape

Another direct-to-retailer release, it doesn't get much better than the comic stylings of Random Terrible Impersonation Guy. And yes, it keeps up that pace for the full nine minutes.

Chandler and Rachel Sell WIndows 95

Billed as the "world's first cyber comedy," this Windows 95 instructional video features Matthew Perry and Jennifer Aniston selling out like there's no tomorrow. No joke: this lasts for 40 minutes, spanning this and three more videos.

"Shoe Circus"

The plan, apparently, was to get Jerry Seinfeld and Bill Gates in a room together and just let things happen. Unfortunately a commercial about nothing doesn't make nearly as much sense as a sitcom about nothing. This campaign cost $300 million, people. Let that sink in.

"Laptop Hunters"

This is Lauren. If she can find a Windows laptop she likes under $1000, she gets to keep it. And she'd better have, because she was a paid actress! Which, fine, but the ad itself is also kinda lame.

"Financial Planner"

Wes Moss: certified financial planner, genuine douche. But what's worst about this ad isn't its slimy spokesman. It's the specious logic that actually works to undermine all the things that were so great about Zune when it first launched.

Kin Hipsters

This Kin spot caught a lot of flack for containing "sexting," but the guy taking a pic of his chest doesn't bother me nearly as much as the sad, aggressive hipster courting that went on with Microsoft's whole Kin campaign.

"Double Rainbow"

I'll say this for Microsoft: they seized on the double rainbow meme right quick, with not one but two online ads featuring Bear, the Double Rainbow guy. I'm glad he cashed in and all, but I wouldn't trust his camera choice any more than I do his hairdo.

Those are just our top picks—there are many, many more terrible Microsoft ads out there, so please post your favorite in the comments.