‘Friends’ Is Iconic, But This Windows 95 Tutorial With Jennifer Aniston And Matthew Perry Is Not


Can you think of anything more ’90s than an instructional video for Windows 95 starring Friends sensations Jennifer Aniston and Matthew Perry? Yeah, we didn’t think so. We recently dug up that very video, and we can’t believe what we’re seeing.

Jennifer Aniston And Matthew Perry Visit Microsoft Headquarters

In the mid-90s, Microsoft capitalized on the popularity of the sitcom Friends by casting Jennifer Aniston and Matthew Perry in a video guide for their new software, Windows 95. At the time, Friends was raking in rave reviews for its first season. People were already dying to know when Ross and Rachel would get together, and women all across the country were asking their hairdressers for “The Rachel.”

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So, it was a smart move for the company to get these familiar faces to promote their product. However, we have to say, Perry and Aniston are batting well below average. To start off, a voiceover described the revolutionary abilities of the new software. Then, it even suggested that you could create your very own sitcom with its video editing feature. So, what was in store for the rest of the video? Well, “the world’s first cyber sitcom,” of course.

That’s when the video sent it over to Aniston and Perry who were supposed to be visiting Bill Gates’ office. However, before they could get starstruck by the CEO, a low-level Microsoft employee named Chip who seemed to be doing a bad Bill Gates impression began telling them about the product.

Microsoft Showcases The Power Of Email

As the video goes on, Aniston and Perry play warped versions of their Friends characters. Aniston rejects the mailroom guy’s advances while Perry makes himself laugh with his witty quips. This is clearly meant to keep the viewer engaged as the real star, Chip, showcases just what Windows 95 is capable of.

He instructs Aniston and Perry on how to get the computer connected to dial-up, and then he gives them an overview of the software. At the climax of the riveting video, Perry sends an email to his friend inviting him to join him a Gates’ office. To wrap things up, Chip annoys Aniston by showing her photos of cats.

The video just proves that star power isn’t enough to carry a clip. However, cringe-inducing jokes aside, the video is a remarkable thing to look back on today. It’s just a reminder that, while Friends is timeless, technology has come a long, long way.

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