Oh, Microsoft. For some reason, they have a history of making really bad commercials and promos. There’s something about them that makes them really good at making really bad videos. Some of them are so bad that they’re funny, while others just make you wonder who actually watches this stuff.

Here are a few videos to watch if you’re bored. Yes, they are real, and yes, they are all made by Microsoft. And yes, I have the same question to: “What were they smoking?”

Windows 386

What: The description on the Google Video page explains it all: “Microsoft sent this tape to retailers to explain the benefits of Windows 386. Boring until the 7 minute mark when the production is taken over by crack-smoking monkeys.”

When: 1988.

I’ve actually grown to love this video. It’s so horrid that it’s hilarious. It’s as if Microsoft was trying to make their own “Pants on the Ground” while adding in a cheesy Mission Impossible-esque theme. W-W-W-Windows, Windows, Windows 386! Okay, I’m done.

MS-DOS 5.0

What: In an effort to promote MS-DOS 5.0, Microsoft hired a guy in a lab coat and three backup singers to make a rap video.

When: 1990-ish.

Wow. Windows 386 must have been such a “hit” that they decided to keep the formula. Or maybe this qurkiness was an 80s thing. I dunno.

Okay, so Microsoft ads in the 80s were terrible. I’ll spare you the pain and fast forward 20 years. Let’s see how Microsoft is doing now.

Songsmith

What: Microsoft is showing off its hot new product, Songsmith! Just sing into a microphone, and Songsmith will add the background music for you!

When: 2009

Yes, this is a real product. And yes, the little girl in the video is using a Mac with cute flowery stickers covering up the Apple logo. While the Windows 386 and MS-DOS videos were hilariously bad, the Songsmith ad is just bad. Yeah, just… bad.

This video actually spawned several more videos. Let me explain: Songsmith takes any audio and generates background music for it. So, many people wondered what would happen if you took a popular song, stripped out everything but the singer’s voice, and had Songsmith add in the rest?

Here are a few memorable Songsmith creations:

Oh my gosh; the last one’s just terrible. @_@ Poor Johnny Cash.

Considering that in two decades, Microsoft has progressed from its quirky Windows 386 promo to  its ghastly Songsmith ad, I don’t think we’ll be seeing the last of Microsoft’s bad videos. I’m envisioning that Microsoft’s ads will continue to torture us for years to come.

Oh well. At least they try, right? :)

Photo by napfisk