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Rediscovering a 1994 Monty Python CD-ROM Through Virtualization

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My basement serves as a testament to the vulnerability of beloved technology, filled with gadgets from the past three decades. It's a chaotic mix of computers lacking media, media without drives, peripherals disconnected from ports, and software that no longer aligns with current operating systems.

Among these artifacts is my collection of CD-ROMs from the mid-1990s. Unlike regular music CDs, which are also outdated, CD-ROMs were the first applications of their kind, featuring games, educational content, and my favorite hybrid genre: edutainment. These were primarily designed for children, with titles like Pajama Sam exemplifying this blend.

I gathered this impressive assortment while working on the PC Magazine's Top 100 CD-ROMs feature. For a while, my kids and I enjoyed many of these discs, but eventually, they outgrew them, as did my Windows systems.

Microsoft has done a commendable job of maintaining backward compatibility for older software, yet there are limitations. Nowadays, most of my CD-ROMs are incompatible with Windows 10, even when using compatibility mode.

I don’t feel the need to run all these titles. Many, such as Phone Disc (a digitized directory of white pages), Encarta (a precursor to Wikipedia), Microsoft Cinemania (a movie database before IMDb), and DeLorme Map ’n’ Go (a static map and directions CD), hold little relevance in today's GPS and smartphone-dominated world.

However, I yearned to revisit titles like Monty Python’s Complete Waste of Time, Duke Nukem 3D, A.D.A.M. The Inside Story, and Star Trek: The Next Generation: Interactive Manual. Unfortunately, Windows 10 shows no interest in running them.

Yet, technology—along with its enthusiasts—often finds a way.

Embracing Virtualization

The optimal method for running obsolete software is not by forcing it onto your current operating system but by utilizing its original OS through a virtual machine.

Virtualization allows one operating system to host another, provided it has sufficient space and memory. This concept has been around since the dawn of computing. Today, there are various virtualization tools available, such as Parallels, which enables Windows to run on Mac, and Microsoft’s Hyper-V for running different Windows versions on modern machines.

Virtualization serves not only to run an operating system within another but also as a secure way to test software, creating a controlled environment that keeps the activities of virtualized applications separate from the host.

Though I have been aware of virtualization for years, I only recently found it necessary.

Getting Started

I initially aimed to use Microsoft’s Hyper-V, but despite enabling it, I struggled to figure out how to operate it. Operating the virtualization system is just one part of the process; I still needed to install an entire OS.

After searching online, I came across Oracle VM VirtualBox, a free and user-friendly utility. Installing it was straightforward, but the software itself serves as a blank canvas; you must add the operating systems.

Oracle VM VirtualBox is a comprehensive program that remains simple enough for anyone to create a virtual machine, featuring large, colorful buttons for adding, managing, and deleting virtual systems.

To add an OS, you require a disc image (commonly available online as ISO files) or the original media. Fortunately, I possess copies of various Windows versions, including Windows 7 and Windows XP (but sadly, not Windows 95 or 3.1). VM VirtualBox even allows installation of 64-bit versions of older operating systems, developed before 64-bit CPUs became standard.

However, setting up these virtual machines proved to be the easy part.

Overcoming Challenges

The key to a successful virtual machine experience is not just installing an old OS on a contemporary computer; it’s about bridging the gap between your modern setup and the pixelated past through current drives and folders.

While these virtual machines consume space on my host computer, they don’t significantly affect performance. If you enjoy hearing the nostalgic launch and shutdown sounds of Windows XP and Windows 7, the experience is worth the trade-off.

Since these older operating systems were not designed for high-resolution displays, they open in relatively small windows. Fortunately, Oracle VM VirtualBox supports screen scaling, allowing the OS to expand to full screen. The first time I tried this, I lost access to my host system, causing a momentary panic.

The default key combination to regain access is the right Ctrl key, which I discovered my Surface Type Cover Keyboard lacks. After regaining control, I found that I could reassign my host access key combination, thanks to a helpful YouTube tutorial.

Despite successfully installing Windows 7 and Windows XP virtual machines, I was unable to access the CD drive used for their installation. As a workaround, I attempted to transfer the contents of a classic CD-ROM to a host folder to access them through the virtual machine.

I quickly realized that the only way to access host drives and folders is by creating shared spaces. Another YouTube video guided me through setting up shared folders and drives, including permissions for read and write access. Even with this setup, I still couldn’t install any CD-ROM files.

The solution appeared to be recreating the entire environment and attempting to run these applications directly from the CD drive, which required enabling USB port access in my virtual machines.

It turned out I was missing some necessary software. Following another YouTube tutorial, I installed a VirtualBox extension file that granted my Windows XP and Windows 7 virtual machines access to the CD drive.

Let the Games Begin

What I achieved can be considered a qualified success.

As I had hoped, titles like Monty Python performed just as they did when first released in 1994, providing the same silliness, non-linearity, irreverence, and entertainment as it did 27 years ago. I even managed to excite Eric Idle, one of the founding members of Python.

Once considered cutting-edge, A.D.A.M. (Animated Dissection of Anatomy for Medicine): The Inside Story now appears quaint with its basic 256-color graphics and modest fig leaves (which can be removed).

The Muppet Treasure Island wouldn’t run on Windows 7 or XP, and Muppets Inside ran on Windows 7 but performed poorly.

Star Wars: TIE Fighter (1995) functioned on Windows XP, albeit without sound—an issue that often arises as classic applications seek out Sound Blaster cards, unable to connect with modern audio systems.

I encountered numerous crashes and odd error messages, including instances where CD-ROMs demanded a minimum of 256 colors despite my system’s capability of displaying millions.

Many of my cherished CD-ROMs, like Duke Nukem 3D, run best in DOS, requiring access to the command screen hidden under Windows XP.

Numerous titles remain unplayable on either platform, including Star Trek’s Interactive Guide and Pitfall!

Some games required considerable effort to initiate. Wing Commander IV, a thinly veiled Star Wars imitation starring Mark Hamill, seemed to freeze each time I attempted to launch it. I eventually realized it only accepted input from the arrow keys, and not very well at that (the compatibility of mouse and trackpad controls varied by title).

When it finally ran, the cinematic, choose-your-own-adventure game suffered from audio lag and stuttering video. The arcade-style missions had more key controls but remained unplayable. Nonetheless, it was entertaining to see a young Mark Hamill and Tom Wilson (Biff from Back to the Future) in action.

Some of my old favorites may never run again. These virtual machines are imperfect replicas of outdated operating systems, lacking complete access to or understanding of their hosts' hardware. I suspect this disconnect is responsible for the failure of some of the more delicate CD-ROMs.

That said, I’m not ready to abandon this nostalgic journey and intend to continue exploring our CD-ROM legacy.

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