Microsoft’s got a pretty stellar track record of terrible Windows infomercials. Some for the consumer, some internal, all pretty rough. This 1988 video showcases Windows/386, a fairly impressive upgrade to Windows that introduced multitasking among other features. The impressiveness of the upgrade does not come through in this video. What begins as a dry-but-corny corporate video quickly pivots into a brief nightmare before returning to its dry roots for a quick finish.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Linda-500x375.jpeg)
The video features Linda, a loyal corpo who’s been given a clandestine set of instructions: come up with the perfect presentation. This premise, presented as a Mission Impossible-style undertaking is high-school video production-level clumsy. This is what a church staff would produce for their holiday party, not one of the biggest companies in the world.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Tape-500x375.jpeg)
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Disks-2-500x375.jpeg)
Linda gets to work, casually noting features of Windows/386 as she builds her deck. She takes a break to give a coworker a quick and specific hard sell on Windows/386, then gets back to work on some “serious crunching”. This is when it gets weird.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Rap-500x375.jpeg)
Linda starts “rapping” to herself about “Windows, Windows, Windows 386”. As she raps we see garments coming off. A coworker enters the office and is shocked to see Linda in a completely insane outfit.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Reveal-500x375.jpeg)
She dials up the rap with her coworker, if “dials up” can correctly capture what she does. It gets more cartoonish, more flagrantly upsetting to both coworker and viewer.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Rap-2-500x375.jpeg)
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Pair-500x375.jpeg)
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Reaction-500x375.jpeg)
Then, just as quickly as she turned, Linda turns back into normal boring Linda. The video concludes unremarkably with Linda delivering her report, receiving accolades, and accepting flowers from a handsome stranger.
![](https://www.timidfutures.com/wp-content/uploads/2021/02/Kiss-500x375.jpeg)
Truly bizarre; I don’t understand who this video benefits.
-ds