The Worst Microsoft Advertisement EVER (Hint: Windows 386)

by John P.

windows-386-promo-videoLook, any time you’ve got a character in an advertisement named T-Bone it’s an indicator of things to come. But after the first 7 minutes of brutally bad acting and terrible story line the good news is that you are treated to a horrible rap song about Windows 386!

Seriously. If you can sit through this entire 12 minute promotional video without your head exploding I’ll be very impressed. It’s just sooo bad. I only finished it myself as an experiment to make sure I wouldn’t kill any of you by actually exposing you to this crap.

Here is the description from whoever posted this video:

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.

By the way, someone please tell me what exactly she is doing with the guy who came to “help” her at the 9:00 mark.

PS – Did anyone else notice that the receptionist’s accent changed from crazy southern belle to nasaly Manhattan in about 3 seconds flat?


{ 11 comments… read them below or add one }

1 Dawn June 12, 2008 at 9:22 am

You’re right, that WAS pretty bad, but the nerdy side of me found the historical perspective very interesting. The funny thing is, I don’t remember ever even HEARING about Windows/386. I must have skipped a version or two along the way. ;)

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2 Balend N June 12, 2008 at 11:38 am

Wow, besides being the worst ad, it was one of the longest as well. Oh, I’ve never heard of windows 386 either.

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3 Lisa Marie Mary June 12, 2008 at 2:26 pm

Bad, bad, bad, and some more bad! LOL! That was so funny! Oh, those big, sexy glasses of hers and that fab little bowtie outfit! (I used to love those things! Shhh!)

I wonder how the board meeting went when they decided that this corporate white woman should do a rap! Haha!

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4 Average Joe American June 12, 2008 at 10:39 pm

That has got to be some of the funniest stuff I have ever seen! I don’t remember a version of Windows older than 3.1, but interestingly enough, I do remember that song she busts out with at the 7:00 mark. Can’t remember where I’ve heard, but I’ve heard it before. What will Microsoft do for entertainment when Bill Gates has completely stepped down in next month or so?

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5 Steve Elliott June 13, 2008 at 5:28 am

Your mission….if you choose to accept it…is to look bad in the biggest glasses and red spray-in-hair ever seen in an ad!

Whatever she was doing at the 9.00 mark, the guys eyes suggested he was enjoying it!

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6 Urbanist June 14, 2008 at 1:41 pm

Is it wrong that I find her sexy? :P

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7 Forumistan June 16, 2008 at 10:23 am

Shes not sexy, and the video is waste of time.

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8 darkheart June 16, 2008 at 12:04 pm

it almost killed me…

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9 Tom Barr July 23, 2008 at 9:41 am

What happens at the 7 minute mark is one of the Go-Go-s (trying to be Pat Benatar) raps (actually hip hops) her way into a Thriller-like music video and comes off Madonna-like. Wasn’t that obvious.

BTW, this isn’t an ad, it’s a hype video they’ve play at a MS developer’s conference. If you have memories of what life was like before cutting and pasting, this is actually pretty cool stuff.

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10 Kitz March 15, 2009 at 8:46 pm

if i am correct, windows 386 was a special version of windows 2.

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11 Kitz March 15, 2009 at 8:47 pm

yes :lol:

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