90s Nostalgia: Remember Jennifer Aniston And Matthew Perry's Windows 95 Introduction?

Many of us refuse to acknowledge that 1995 was almost thirty years ago. It just seems impossible. The mid-nineties was a very special time, a time marked by the release of the original PlayStation (September 1995 in the United States), some fantastic Saturday morning cartoons, the height of the Friends phenomenon (the show debuted the previous September on NBC), and Windows 95, which was also a phenomenon. Did you know, though, that both those phenomena collided in glorious fashion?

You may have seen it on social media marked something like "the most nineties thing you can possibly ever imagine happening." You might even have owned it, or still own it. Regardless, Jennifer Aniston and Matthew Perry, Friends' own Rachel Greene and Chandler Bing, brought us the Microsoft Windows 95 Video Guide.

Aside from their enormous cultural cache at the time, it's hard to say what qualified the pair to introduce the world to the computing paradigm shift that was Windows 95 (Windows 11 continues to boast some useful tools), but that's exactly what they did. Surprisingly, the Video Guide, which was released (on VHS of course) ahead of the iconic OS, was quite in-depth and informative among all its silly comedy. Let's take a look back at what it had to offer over its approximately one-hour duration.

With the ubiquity of streaming services today, you could technically call any streamed sitcom a "cyber sitcom." In the time before such services, though, the Microsoft Windows 95 Video Guide offered what it proudly deemed to be "the world's first cyber sitcom" (John Deam on YouTube). This amounts to an extended skit at the beginning of the video, in which Aniston and Perry get up to all sorts of hi-jinks in Microsoft's headquarters. Cheesy jokes, such as the pair thinking that everybody applauds when entering Bill Gates' office when his assistant Bernice was simply activating the clapper for his lights, are supplied as standard.

Aniston, a self-professed computer amateur (in the context of the guide), confuses the Taskbar with a Snickers bar, and through such interplay, Bernice explains to her, and to the viewer, Windows 95's new features and what they do. Within a couple of minutes, Bernice has detailed everything from the Programs menu (the successor of Windows 3.1's Program Manager) to the new Control Panel and the three-pronged Shut Down menu.

It's quite a clever format. It's strange to think that there was a time when the likes of minimize, maximize and My Computer were brand-new features in computing, but the appeal of these two TV stars and the "edutainment" approach of this so-called cyber sitcom surely helped many prospective users get their heads around Windows 95 before (and indeed after) the time came to use it for themselves.

Amid the undeniable hilarity of Start menu/restaurant menu puns, viewers should never forget that the guide's primary purpose is just that: To introduce Windows 95's suite of new features, down to the fact that it allowed 250-character file names of the user's choosing. After around thirty minutes, the pair leave having unfortunately missed Bill Gates himself, but gleaning a lot of pearls of wisdom from various Microsoft employees (or actors playing them).

At this point, the guide reverts to a more conventional, instructional format, which recaps those functions through a series of on-screen tutorials. The final aspect of the guide is a rundown of the answers to twenty common questions about the operating system, such as "What are the system requirements of Windows 95?" and "How do I create shortcuts on the Desktop?"

To call Windows 95 widely used would be an understatement: In August 1996, Microsoft reported that it had already been shipped to 40 million customers. It's probably safe to presume at least some of those people were Friends fans. Today, Windows 11 continues to have its issues, but celebrities or no celebrities, it's still a big name in the PC world.