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The Most Cringe-Worthy 90s Internet Guides That We Can't Stop Watching

The 90s were an interesting time.

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Back in the 1990s, we installed new software by using physical disks, and at the time, it wasn't always so easy to figure out how to use the dang programs, like Windows 95, unless you wanted to read the manual, which is not much of a page turner. The internet was also so new that commercials and how-to guides were all over the place—on VHS, television and the internet itself.

We rounded up some of our favorite commercials and internet guides. In the process, we laughed, we cried, we wondered why everything had to include such bad acting. But mostly, we learned how lucky we are to have digital tutorials to click through today.

Rachel and Chandler Take on Windows 95

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Most of us don't read instructions for new versions of computer operating systems. An update dialogue box pops up, we either install the update or keep smashing the "remind me tomorrow" option until we finally cave.

In either case, we know almost everything we need to upon rebooting the computer—we're living in a generation where operating systems come to us intuitively after years of practice.

Not to mention, computers, smartphones, and tablets typically walk you through new software updates to show you the new features.

Back in 1995, though, Jennifer Aniston and Matthew Perry were the ones walking us through how to use Windows 95. Part of the joke is that Rachel is actually sitting at Bill Gates's desk, using his computer to demo Windows 95—to which Chandler replies, "That's like playing hockey with Wayne Gretzky's hockey stick!"

Kids' Guide To The Internet

In this gem, the fictional Jamison family discusses how much they love their new computer and internet hookup. The family is teaching their friends how to take a spin on the internet. They talk about what search engines are, how it can help them do homework and how to type in a web address.

"I'd rather be on the internet than doing just about anything," the brother says, facing the camera.

"I guess this is the story of how it changed our lives," he goes on to say. "Maybe it can change yours, too."

It's corny and worth every single moment.

AOL Commercial, 1995

"Everyday, America Online is making it easier for people to live, work and play," a narrator opens the scene.

Two guys discuss sending flowers to their mothers through a website on the internet, which blows the mind of the man without the computer. Meanwhile, the other guy boasts that AOL will give you the software through the mail and allot you "10 full days to check it out!"

There's a phone number listed to get your start-up kit for Windows or Mac. I called it and, alas, it's now just a telemarketing company.

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President Clinton at an Online Town Hall Meeting, 1999

We live in an era of Congresspeople who, by majority, have no idea how Facebook's advertising business model works or have any clue how blockchain, 5G, hacking or other matters of internet business work.

But there were simpler days, where the focus on technology was fixated on the forum, not the content. In this 1999 virtual town hall meeting, citizens could ask questions through an online portal that former President Bill Clinton and the moderator could receive through their monitors.

The "excite chat" site that's mentioned is defunct, but here's a screen grab from the Wayback Machine.

Julia Stiles in "Ghostwriter"

Super edgy nose ring and floppy beanie hat aside, a young Julia Stiles uses that spitfire attitude of hers that we all love. But in this clip, from the sitcom Ghostwriter, she's an editor at her school's newspaper and the kids are writing about hackers.

When one of the other students asks to write the article, Stiles goes into a long dialogue of fancy-schmancy internet terms to flex her superiority.

"Do you know anything about hackers?" She asks with a slight roll of the eye.

"Ever read Neuromancer?" she asks, to which the other girl just says, "huh?"

How Computers Work: A Journey Into the Walk-Through Computer

"There still seems to be this aura of mystery and complexity surrounding them. It's almost like we're in an electronic brain or something," says the narrator.

He's here to dispel myths about the computer and to answer questions like, why one kid accidentally deleted his homework assignment by pressing the wrong button.

All the kids lament that they don't know how computers work, so they actually take the computer apart. Honestly, it's a little informational.

Then they go to a computer museum to walk through a giant replica of a computer to learn about its parts at a life-size scale. It's pretty trippy but probably helped a lot of people at the time.

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Komputer Kindergarten

With a title like that, you know you're in for a treat.

Rolodex and whiteout used to be on our narrator's desk, but now she has a printer and a computer and floppy disks.

True to the title "Komputer Kindergarten," the narrator uses lots of metaphors and similes to make comparisons to the computer. She explains how to play solitaire, find the time, and even...click things. And write things.

Internet Users Guide From 1990

The characters are ready to go "surfing!" If they can figure out what that means outside hitting the waves.

In the video, a woman has to explain how the technical parts of the computer work to an older man. He's goofy and makes bad jokes about web surfing, email, and images of classic paintings.

He even asks, "Do all browsers look like Netscape?"

It all comes together when our male computer noob lands on a NASA webpage all about space, which utterly blows his mind.

Steve Ballmer Ballin' Out

Okay, this isn't really a guide, but we just really like this video of former Microsoft CEO Steve Ballmer screaming "developers."

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Courtney Linder
Deputy Editor
Before joining Pop Mech, Courtney was the technology reporter at her hometown newspaper, the Pittsburgh Post-Gazette. She is a graduate of the University of Pittsburgh, where she studied English and economics. Her favorite topics include, but are not limited to: the giant squid, punk rock, and robotics. She lives in the Philly suburbs with her partner, her black cat, and towers upon towers of books.
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