Jennifer Aniston and Matthew Perry’s Windows 95 tutorial video, revisited.

Jennifer Aniston and Matthew Perry’s Charming Windows 95 Tutorial Shows Tech Giants Used to Fear Us

Jennifer Aniston and Matthew Perry’s Charming Windows 95 Tutorial Shows Tech Giants Used to Fear Us

The citizen’s guide to the future.
Sept. 14 2017 2:26 PM

Jennifer Aniston and Matthew Perry Guide Us Through Windows 95

The charming tutorial shows tech companies used to fear us.

Photo illustration by Natalie Matthews-Ramo. Photos by TBS and Thinkstock.

Photo illustration by Natalie Matthews-Ramo. Photos by TBS and Thinkstock.

In the mid-’90s, Microsoft relied on some friends to help teach people how to use their brand-new operating system, Windows 95.

We’re talking Friends friends Jennifer Aniston and Matthew Perry, stars of a long video that fairly reeks of the Must See TV sitcom aesthetic, filled with non sequitur introductions of wacky characters. (Highlights in the video above.) Strangely, it’s not bad. Definitely not as bad as you’d think based on the central conceit: Aniston and Perry arrive at Bill Gates’ office for a casting call for a Microsoft video, and Gates’ personal secretary takes them on a helpful tour of the new operating system.


Tellingly, this is an instructional video rather than an advertorial. It was still two years before Steve Jobs returned from exile to lead Apple, 11 years before John Hodgman would come to embody the stodgy PC running Microsoft’s operating system. Microsoft was riding high, and Bill Gates wanted a PC running Microsoft in every home. It looked like he might get it.

Yes, the video features its share of groaners. Perry learns to address an “internet email” to a friend in a grunge band while the geeky, Gates-like mailroom guy assures the friends that “communicating online is the hot thing right now, and the Microsoft Network is your on-ramp to the information superhighway.” Then he looks up some cat photos. Cat photos are eternal.

But putting aside the outdated nomenclature, the video is a fairly deft introduction to a future that was still foreign to many. A Pew study from October 1995 found that only 20 percent of “online” users actually  went online daily, and only 32 percent said they would miss the internet if they couldn’t use it. The “World Wide Web” was just two years old, and people connected to it on modems over their home phone lines. The average email user sent three messages and received five each day.

So this video was less a guide to what was than an argument for what could be: a prediction, albeit one coupled with an invitation and barely hidden sales hook. It has a hopeful quality that’s downright quaint to revisit in a week that brought us bumptious executives hailing the corporate “town square.” It’s charmingly solicitous, inviting us into its world rather than telling us how it plans to upend ours. Maybe an iPhone X commercial is the real Friends reunion we need.

This article is part of Future Tense, a collaboration among Arizona State University, New America, and Slate. Future Tense explores the ways emerging technologies affect society, policy, and culture. To read more, follow us on Twitter and sign up for our weekly newsletter.

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Jon Kelvey is a writer and journalist based in central Maryland.