Windows 10 is happening, and you may or may not be running it by this evening, depending on whatever magical factors are used by Microsoft to determine availability. Upgraders will experience what our own Peter Bright calls a not-quite-perfect Start Menu and (at least eventually) some hot DirectX 12 gaming action, but something else is missing from the launch.

See, in years past, as a new version of Windows charged toward release, Microsoft always released a little something extra—a promotional video.

This is not a Microsoft-exclusive idea. Every company releases marketing-driven promotional videos, and they range from ludicrously overblown ballads to hilariously insulting and condescending how-to videos. But Microsoft’s promo efforts stand out even in this sea of crap.

I think it’s because in each video, everyone is trying too hard. Rather than the actors giving off a "tongue-in-cheek, we’re-in-on-the-joke" vibe, the videos instead feel like forced death marches. They’re almost Onion-esque in their absurdity, except where The Onion would end an idea when the comedy was over, these videos just keep going.

We’ve assembled a half-dozen of the best (read: worst) promotional videos Microsoft has put out. Almost all are about operating systems, but we couldn’t resist adding in Microsoft’s infamous Songsmith video—something so terrible that it almost deserves its own article.

W-W-W-Windows! Windows 386!



Let’s say you have a new version of Windows that you’re aiming squarely against IBM’s OS/2 (and you’re still a bit sore about the whole OS/2 thing in the first place). You need to explain to potential customers that your new operating system does the same kind of stuff that OS/2 does, like graphical multitasking, windows that can overlap, and even fancy OLE connectivity between applications.

Do you simply take out an ad in The New York Times and maybe give a few interviews to PC Magazine and Byte? Or do you produce a 12-minute promotional video that starts off as a Mission: Impossible spoof and ends up in an epic synth-backed rap-off with massive '80s hair and spreadsheets flying everywhere?

If you’re Microsoft’s marketing department, of course you go with option B.

(If you want to skip the terrible build-up and just watch the train derail and plow into the fuel dump, skip to 7:10 in the video. Good luck, and God be with you.)

Windows 95 and what Microsoft thinks of you



Windows 95 introduced many new capabilities to the Windows world, and Microsoft produced a bunch of videos diving into various aspects of the new operating system. Sounds like a good idea—after all, one of the things Windows 95 was able to do was play video better and more consistently than Windows 3.1 and 3.11, so promo videos had synergy!

Watching this video, though, doesn’t make me think of "synergy" at all. It makes me think of sadness and ruin.

The video is clearly trying to be "fun" with its presentation but instead comes across as miserable, degrading, and condescending. The narrator sounds like a refugee from a cancelled children’s show, and the poor actor suffers through costume change after costume change, going from an offensive French stereotype to a surfer dude stereotype to a nerd stereotype to… well, just watch.

We’re all Friends here, right?



Perhaps one of the most famous promotional videos of all time, this "cyber sitcom"—I can’t believe I just typed those words—features Friends actors Jennifer Aniston and Matthew Perry sneaking into Bill Gates’ (fictionalized) office and being lectured on the new features of Windows 95 by Bill Gates’ (fictionalized) secretary.

This seems absurd today, but remember that this video hit in 1995, right when Windows 95 was released to the general public. At the time, Friends was still climbing in popularity and—ha, I’m sorry, I just can’t do it. I can’t keep going here. Look, we sold this video at Babbage’s when I worked there, and we thought it was just as stupid then as it is now.

Aniston and Perry riff off each other with flat jokes, and you know when you’re supposed to laugh because there’s a dumb little musical sting after every one of them. Aniston plays dumb and Perry plays wise-ass, and even flipping through the video for this write-up gave me suicidal thoughts. If you can watch this entire thing, even drunk or high, you are superhuman.