Microsoft Windows 95 Video Guide (1995) — The One with the Cast of Friends

“Look, Matty, I’m computing!”

Justin’s rating: START watching this masterpiece

Justin’s review: For today’s review, we’re going to take a weird sidestep out of cult films to cult… instructional videos? Wait a minute! Don’t run away, this one is worth your while, trust me.

So in 1995, Microsoft spent somewhere in the vicinity of $300 million to market its brand-new operating system, Windows 95. They dragged Jay Leno out to josh with Bill Gates, they paid for the rights to use Rolling Stones’ “Start It Up,” and, for the target of this review, they roped in two stars from NBC’s Friends to be featured in an hour-long video designed to walk clueless yet trendy computer users through interacting with Win95. And let me tell you, this is a thing of beauty and embarrassment and ’90s time capsule potential.

At the start of what the narrator weirdly labels “the world’s first cyber sitcom,” we are outright promised no less than three times that it will make us laugh. In my experience, that’s always a sign that nothing funny whatsoever lies around the bend but rather plenty of cringe moments. What we have here is a thinly veiled tutorial for Windows 95 masquerading as some sort of weird sitcom. Note that while there’s no laugh track, there is a Seinfeldian slap bass that happens when “jokes” are told, just in case you didn’t know when it was appropriate to laugh.

So Jennifer Aniston and Matthew Perry — sort of playing their Friends characters, but not by name because of copyrights — show up at Microsoft, where Bill Gates promised to show them Windows 95. I don’t know, maybe random celebs did this to Microsoft back in the ’90s, so I’ll let it go. Anyway, Bill is not there, but his secretary has no problem letting Jennifer and Matthew into his office (!) and onto his personal computer (!!) for the purposes of teaching them the pure wonder that was this revolutionary operating system.

What follows is a lot of unfortunate wordplay, over-enthusiastic description of the simplest of features (“Minimizing a window? WOW!”), and even an attempt to upsell viewers to buy the Microsoft Plus addon pack. This all seemed pretty rote and wouldn’t make for a truly legendary video, so after a few minutes of Perry and Aniston pretending to be enthralled by a 40-pound CRT monitor, other characters start showing up in the room to tag-team into this Windows 95 presentation.

They’re… man, how do I put this? They’re characters created by focus groups made up entirely of well-meaning but largely clueless 40-year-old moms. We’ve got a fat window washer with his own confusing European theme music. There’s “The Chipster,” who really needs a haircut. Many stereotype boundaries are broken by the incredibly white Chinese food delivery guy who does martial arts, speaks in broken English, and offers fortune cookie platitudes. At the end, a grunge band shows up and I am totally not making that up.

But nothing will prepare you for the debut of JOYSTICK JOHNNY. Trust me, nothing. Your entire life will forever be separated into two eras: The Before, and every minute after you witnessed Joystick Johnny. He’s a skateboarding gamer (with a rearview mirror on his helmet, why not) with a strong case of Lingo who is really, really, really into… video pinball. If Joystick Johnny ever ran for congress, I’d vote for him.

I’ve seen this video referred to as “the most ’90s thing ever,” and I might have to concur here. It’s not just the characters, although they certainly add a lot of local flavor. So many computer references are blissfully ignorant and innocent, especially when The Chipster logs them into the “information superhighway” for a little internet surfing. What do they instantly do? Go check out cat pictures. Clearly, civilization has advanced so far since then. Ahem.

For those of us who were there for the launch of Windows 95, this video is an amazingly good reminder of why we thought it was darn cool at the time. So many of the features that we’ve since grown accustomed to having are presented here like these people have never heard of them before. What I’m saying is that there’s an added layer of nostalgia for certain demographics.

It’s not funny — at least, not in the way the creators intended — but the delightful combination of cringe moments, antiquated references, Friends actors collecting what I assume is a very fat paycheck, and an elaborate explanation for what “multitasking” is makes this a weirdly compelling watch all the same.

Didja notice?

  • Those horrible ergonomic keyboards that were so popular for a while there
  • “The World’s First Cyber Sitcom” sheeeeesh
  • “Task bars and emails and shortcuts oh my”
  • The Seinfeldian bass music
  • How do you know you’re in the ’90s? The Clapper.
  • Jennifer is “still mastering Pong”
  • “Taskbar? Is that like a snack bar?”
  • Copying a file is “trippy”
  • We wish you a Perry Christmas
  • Everyone gushing about longer file names. Man, that takes me back.
  • “The recycle bin is the enabler for the undecisive?”
  • MULTITASKING
  • Lotsa fat jokes, there
  • Online ordering is going to blow these people’s minds in a decade. These guys? They’re going to fax from the computer. Fax. Kids, it was a thing, ask your grandparents.
  • The help screen never was that exciting
  • Boris comes with his own confusing theme music
  • PLUG AND PLAY
  • The Chipster is a little aggressive
  • Remember back when nobody really knew much about the internet and called it the “Information Superhighway?” Let’s bring that back.
  • DIAL UP MODEMS
  • “Jennifer, do you like cats?” “No.” “Then you’re going to love this!” The Chipster was very ahead of his time.
  • And then the Chinese food arrived by a guy biking through Microsoft’s hallways with a dragon head. When he gets there, he does some lame martial arts. He’s also very, very white.
  • RIGHT-CLICKING
  • Wow, look at those low, low screen resolutions
  • “You did not just say ‘rockin the desktop'”
  • And introducing Joystick Johnny as himself
  • Wow, they’re really trying to upsell Microsoft Plus. And 3D Pinball.
  • Now we’ve got a grunge band.
  • The red button… sucks everyone into the computer?

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