Best Windows Parodies to Celebrate 25 Years of Windows 3.0

Mihir Patkar 22-05-2015

May 22, 1990. Back then, $3 million was a hefty amount, especially for a technology company. But Microsoft pulled no punches in its opening day launch of Windows 3.0 in New York. This was their weapon against the Macintosh and it was the first step in the historical fall of Apple When Did Apple Become Popular? A Brief History of the Rise of Apple How did Apple start and when did Apple become popular? We answer these questions and more in a brief history of Apple. Read More .


In these 25 years The History Of Microsoft Technology [INFOGRAPHIC] We all like to bash Microsoft and Windows, but the truth is that they have been around for so long and given us so much software and technology, that we couldn't possibly imagine a computing... Read More , Microsoft has enjoyed great success, but at the cost of great ridicule. It has released some disastrous products, including its flagship Windows operating system. The company’s products haven’t always been perfect, and the Internet has never shied away from making it the punch line.

It’s the operating system we all love to hate, but therein lies the key. It’s 25 years of a love-hate relationship. Microsoft’s imperfections are a part of our lives; they make us nostalgic, they make us laugh. It’s about celebrating the imperfections, so we trawled through several parodies on the web to uncover the best of the best—and really, there are plenty of unfunny spoofs out there.

If The Matrix Ran On Windows XP

In this hilarious parody, College Humor marries the cutting edge of sci-fi pop culture with the operating system that drives you to the edge. What would The Matrix be like if it ran on Windows XP? You will be cracking up at jokes about Windows freezing to a guest appearance by everyone’s favorite helper Clippy, the Office Assistant. No points for authenticity though since the lead actor emotes more than Keanu Reeves ever did.

Windows 93


After Windows 3.0 in 1990, Microsoft’s next major operating system was Windows 3.1 in 1992 and then Windows 95. But you probably didn’t know that there was a Windows 93 in the middle of all that.


Well okay, there wasn’t, but this spoof OS made by a couple of developers shows you what that would have been like. It encapsulates the experience of an early 90s Windows computer in the best way possible, from a fully functioning version of the classic first person shooter Wolfenstein 3D to silly little bits like a “virtual girl” and a file called “Totally not a virus, trust me, I’m a dolphin!” If you really want to relive the good (?) old angst of early Windows, double-click Hydra.exe. Do it.

Internet Explorer 9 (The Honest Version)

Just when you thought Internet Explorer was finally good Why You Should Upgrade To Internet Explorer 11 Now Restoring Internet Explorer to a browser that people actually wanted to use was always going to be a hard road, but it's just possible that with Internet Explorer 11 this stage has been reached. Read More , Microsoft pulled the rug and announced a new browser Microsoft Gets the Edge, 1 Billion Devices Running Windows 10, & More... [Tech News Digest] Microsoft has the Edge, Windows 10 is huge, Secret gets shut, embed MS-DOS games in tweets, make money from Silent Hills, and watch Michael Bay get shown up by an amateur filmmaker. Read More instead. A few years ago, MS unleashed an ad blitz for the launch of IE9, claiming it was the best browser around. It wasn’t. And YouTubers World Wide Interweb decided to take one of the commercials and try to depict what using IE is actually like with the help of that commercial.

Windows 8 Consumer Preview Parody

Perhaps the most polarizing Windows release in history, Windows 8 decided to cater to both touchscreen users and desktop users. And Microsoft also released a Consumer Preview so people could try it out. Windows 8 didn’t impress anyone My First Hour With The Windows 8 Consumer Preview - A Snap Judgement [Opinion] I want to be surprised by Windows 8; I want to be pushed into a new paradigm of home computing, one that feels futuristic with it's bold colors and simplistic interface; I'm fully prepared for... Read More . More importantly, Microsoft’s “everything is awesome!” toned ads and presentations were even worse, as the company showed off new features that were obviously flawed in many ways. Thankfully, YouTube funnyman Louie Barra is here to walk you through all of them.

Microsoft SAM Sings About XP

You can get Apple’s Siri to say whatever you want How To Get the Siri Voice & Make Her Say Whatever You Want Whether you're creating audio clips for your own weekly technology podcast, or looking to write your own Siri spoof videos - having the Siri voice on your Mac is awesome. Let me show you how... Read More , but she isn’t the first digital talking companion on a personal computer. Microsoft SAM came into our homes with Windows 2000, and apart from his inability to say “soy”, he was not that bad. Or so I thought, but memory can be defective, as The Electric Hippie Orchestra’s little duet with SAM shows. It’s a song about Windows XP, sung by Windows XP, produced on Windows XP.


Windows XP v19.914


Speaking of Windows XP, let’s relive its glory through this wonderfully accurate Flash version of XP. Start up “Internet Venturer” and you are greeted with a message that finally provides the sub-text of Microsoft’s frustrating error messages: “The page you are looking for is currently unavailable. And it’s not like I’m saying you should hold your breath either. It’s easier to blame you, so we will. It’s your fault this won’t work.” Explore the whole OS, the makers have put a lot of work into it, especially MSN Messenger and ChatSlangGirl. Plus, it has Kazaa, you guys!

Google Glass on Windows

We started with thinking about what The Matrix on Windows would be like, so let’s end with something similar. Google Glass is incredible technology Google Glass Review and Giveaway We were lucky enough to get a pair of Google Glass to review, and we're giving it away! Read More , but imagine it being made by Microsoft. You don’t have to imagine because vlakkeland made a little video demonstrating this futuristic experience. Are you sure you want to permanently delete his banana?

A Trip Down Memory Lane

In case all of this has you taking a trip down memory lane, go a little further and check out some of these classic operating systems you can access in your browser 8 Classic Operating Systems You Can Access in Your Browser Feel nostalgic? You can still relive some of the operating systems of old. Enjoy these classic operating systems in your browser. Read More .


But before you go, tell us your oldest or most vivid memory of Microsoft Windows. My first machine was running on Windows 3.1 and I spent an unnecessary/unhealthy amount of time perfectly tiling and organizing windows. It has been 25 years, you know you have some great stories too!

Image credit: LOL computer key by Marco Rullkoetter via

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  1. Frickarlosz
    February 22, 2017 at 8:12 pm

    The XP you're linking isn't working. Try instead, an online XP simulator

  2. Dwayne
    May 23, 2015 at 11:12 am

    I remember when Microsoft was showcasing Windows 98 for the first time, and to nobody's amazement, it crashed during the preview

  3. kt
    May 23, 2015 at 1:11 am

    "This one isn't crap" should be the M$ catch phrase.

  4. John Mayson
    May 22, 2015 at 4:50 pm

    I lived in the Unix world with a beautiful X Windows system. I first used Windows 3.1 in 1992 and my initial reaction was "You've got to be kidding me?". I felt like had gone back 10 years in computer technology.

    • K.I. Matthews
      May 23, 2015 at 12:39 pm

      How does this add to the discussion?