Windows Oddities: 25 Years of Microsoft Weirdness

25 Years of Microsoftian Weirdness

Contrary to popular belief, Windows is far from boring. Dig below the surface, and you’ll discover a stranger side to the world’s most popular operating system. It’s filled with twisted homages, forgotten platforms, and dead ends. In a word, it’s full of oddities.

On the eve of Windows’ 25th birthday–version 1.0 shipped on November 20th, 1985–let’s explore this underground. When we’re done, tell us about the Windows oddities you’ve encountered.

Windows 3.2

Tens of millions used Windows 3.0 and Windows 3.1 - they were the first two versions of Windows that really put Microsoft's graphical interface on the map. But few know that Microsoft released a Windows 3.2-for China only - in 1994. Behind the scenes, this new version shared almost everything in common with Windows 3.11, but it included a few localized icons and updates to support a Chinese character set.

Images: ToastyTech GUI Gallery

Sega Meets Windows

Since its premature exit from the video game market in 2001, the Sega Dreamcast has attracted a large cult following. Ask any one of its fans what logo is printed on the Dreamcast's front right side, and they'll tell you immediately: Windows CE. But few know what it means.

Microsoft created a suite of development tools based on the embedded Windows CE OS for the Dreamcast. Few games took advantage of them, however. And contrary to popular belief, the Dreamcast does not run Windows CE as its primary OS. Instead, it is loaded as needed from a game disc that uses it.

It's rumored that Microsoft's involvement with the Dreamcast inspired the OS giant to enter the console arena with the Xbox in 2001.

Photo: Pixel Fantasy

x86 Optional

What amazing news it was in 2005 when Steve Jobs revealed that Apple OS X- that PowerPC stalwart- was coming to the Windows-dominated Intel x86 architecture. To turn the tables on that scenario, we must travel all the way back to 1995 and the release of Windows NT 3.51, which not only ran on x86 but also on PowerPC, Alpha, and MIPS processors. (NT 3.51 wasn't designed to run on Apple hardware, but on new PowerPC workstations and servers like the IBM R/6000 series.)

Only two years later, Microsoft dropped support for PowerPC processors in its NT operating system line. Few missed it, but NT lived on and later evolved into Windows 2000, XP, Vista, and 7.

A Terrifying Costume

In the world of OS culture, Apple has the Apple logo, and Microsoft has the Blue Screen of Death. With so many users encountering the BSOD in the Windows 98 era, it became a symbol of the uneasy dance between our need for Windows and its primal need to be absurdly unstable. How could something we depended on so much hurt us so often?

Thanks to the more stable NT strain of Windows, the days of plentiful BSODs are over, but the cultural memory remains. It was only a matter of time before someone (like the clever chap seen here) created a costume homage to Microsoft's most legendary error. And he did a fine job.

Photo: Robert Occhialini

Windows 95: The Early Years

Before Windows 95 knew exactly what it wanted to be, Microsoft called it "Chicago." Seen here is an early development version OS (build 58, in fact) that doesn't look very familiar

Instead of a Start button, but there are a few buttons that call up system power, search, and help menus. Instead of a taskbar, we see a white area where shortcuts to programs and documents could be dropped. When programs were minimized, they showed up as large grey rectangles above the proto-taskbar. For more information on how this worked, check out ToastyTech's fascinating examination of this embryonic OS.

Image: ToastyTech GUI Gallery

iPad, Meet WinPad

In the years before Windows CE, Microsoft worked on a precursor pocket operating system called WinPad, seen here in a 1994 alpha version. After the success of Windows 95, the company decided to turn WinPad into a Windows 95-like OS for pocket computers. The first devices to use it were released in 1996.

It's interesting to think that long before there was an iPad, Microsoft had tinkered with the idea of a WinPad. It serves as yet another reminder of how old the "tablet computer" concept really is.

Images: Beta Archive

Show Your Windows Pride

The previously mentioned Blue Screen of Death is back to haunt us again, but this time in t-shirt form so you can show off your nerd cred in public.

It's amazing how hard it is to find a serious Windows t-shirt out there, but you can buy plenty of Apple-related merchandise. I'll let you draw your own conclusions about what that means.

Photos: Errorwear

Windows 3.1 in Disguise

This image may make you do a double take. First, you look at the Start menu, task bar, and the desktop icons and think "Windows 98." But then you see the Start menu label on the left: "Windows 3.11″?

Running atop this geriatric 16-bit OS is an unofficial open source shell called Calmira II that replicates much of the functionality of later versions of Windows to stunning effect. The result is quite impressive. Now if only I could find a reason why I regularly needed to run Windows 3.11.

Image: PC Freak

The Blue Screen of Life

Over the years, we’ve seen quite an array of Windows splash screens (the screen that shows when Windows first loads), including teal boxes, clouds, and subtle glowing logos on black backgrounds. Let’s rewind for a minute to the beginning (1985) and Windows 1.0. You’re looking at the very first Windows splash screen, now 25 years old. It’s not much to look at, but it features Microsoft’s old logo with an “O” that suspiciously resembles the Death Star. Hmm…


Over the years, Microsoft has slapped quite an array of code names across its prototype Windows versions. Chicago, Memphis, Neptune, Longhorn, and Whistler are just a few. Whistler (seen here) bore an airy logo resembling that of a prescription drug or a feminine hygiene product. We should all be thankful that Microsoft didn't keep the name for its final version of Windows XP, which is what Whistler became.

Jokes aside, it's interesting to see Microsoft's early, ultra-fresh take on the eventual Windows XP interface.

Image: GUIdebook

The OS/2 Connection

This looks a lot like Windows 3.1, doesn't it? But you're actually looking at a screenshot of IBM OS/2 v1.3. The two graphical environments are similar because Microsoft developed both Windows and the early versions of IBM OS/2. Not long after this version hit the market, Microsoft and IBM parted ways, and IBM developed OS/2 2.0 on its own. We all know what happened to Windows.

Image: ToastyTech GUI Gallery

Think Ink

In 1992, Microsoft released a version of Windows 3.1 optimized for stylus-based touch input. They called it "Microsoft Windows for Pen Computing 1.0," and it shipped on the early tablet PCs that emerged then.

I happen to own a computer that uses this OS, and it works very, very well, which is somewhat surprising because of both the OS's age and its low profile in computer history. Microsoft later released version 2.0 of Pen Computing based on Windows 95, then XP Tablet PC edition in 2002.

Image: Benj Edwards

A Legal Windows Clone

Have you ever wanted to run Windows without running Windows? Now you can thanks to ReactOS, an open source Windows NT clone that aims to be 100% binary compatible with software written for Microsoft's NT-based operating systems (a la Windows XP).

ReactOS is still in an early Alpha state, but it looks promising and you can download a copy to try yourself. The project could bring good things to low income and third world computing.

Image: ReactOS

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