Nerd Nostalgia

This Windows 95 Tutorial Was an Attack on Cool Kids

In the video that stars Jennifer Aniston and Matthew Perry, the nerds finally get their revenge.

By Matthew Halverson July 31, 2015 Published in the August 2015 issue of Seattle Met

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Image: Youtube

If I asked you to list some of the most regrettable, yet unmistakably defining artifacts of the ’90s, where would “the Rachel” rank? What about comically oversize sport jackets and casual misogyny? Or 25-pound computer monitors and all-white television casts? Now what if I said you could find all of those things—plus the line “Communicating online is the hot thing right now”—in a single, 25-minute tutorial about task bars and spreadsheets and file-naming conventions? “I’m repulsed by and yet curiously drawn to this thing of which you speak,” you might say. Until, that is, you realize it’s all in service of making you the butt of a joke.

Microsoft released Windows 95 twenty years ago this August, a time when—as hard as it may be to believe now—less than a third of the country’s homes had a computer. So to help introduce his splashiest operating system yet to this nation of tech illiterates, Bill Gates cast Matthew Perry and Jennifer Aniston in the VHS equivalent of PCs for Dummies. Perry and Aniston were one year removed from the premiere of Friends and well on their way to being two of the biggest names in prime time comedy; who better to introduce America to intimidating concepts like minimizing windows and installing printers and faxing from a computer?

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Yet watching the video now, it’s hard to imagine that the marketing team at Microsoft saw the country as anything but a horde of drooling idiots who’d sooner throw rocks at a CPU than search for the power button. In fact, it’s entirely possible that this was the geeks’ opening salvo in a retaliatory war on those cool kids who baptized their heads in the toilet between first and second periods. After years of being mocked for knowing too much about computers, they could finally mock those who knew too little.

And so for nearly half an hour we watch as Perry (playing himself) and Aniston (playing a lobotomized version of herself) learn how to use Windows 95 from a “wacky bunch of propeller heads” that includes a Russian window washer, a Chinese food delivery man, a mail room employee, and a preteen gamer named—I’m not making this up—Joystick Johnny. (In other words: If the Friends costars are our surrogates, it’s assumed that we know less about computers than a refugee from behind the Iron Curtain who learned English from watching old Yakov Smirnoff standup.) “Task bar,” TV’s Rachel Green says quizzically while staring blankly at the screen early on. “Is that anything like a Snickers bar? Does it have nougat?” This comes, by the way, not long after a receptionist with a hammy approximation of a Long Island accent insists that Aniston demo the operating system to prove that it’s “goof proof.” Take that, all you hot high school cheerleaders who snapped our suspenders and stole our Star Trek Trapper Keepers!

But if you still need more proof that the nerds are having their revenge, consider this: The scene plays out in Gates’s “office,” where Aniston and Perry have been invited to discuss starring in the tutorial—meta!—only to find he’s mysteriously away on business. Like the popular girl who invites the social leper to prom only to stand him up for everyone else’s entertainment, so too was Gates playing them—and by extension us—for fools.

Or, who knows, maybe he just bailed when he realized what a travesty this video would be.

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