Virtualization Helped Me Unlock a 1994 Monty Python CD-ROM

Ancient CD-ROMs and digital artifacts from the ’90s returned to life on my first virtual machine

(Credit: Lance Ulanoff)

My basement is a living illustration of the frailty of our favorite hardware and software. It’s full of gadgets from the last 30 years. There are computers without media, media without drives, peripherals without ports, and software without operating system support.

Among all that is my collection of mid-1990s CD-ROMs. Unlike music CDs (also a relic), CD-ROMs were the proto apps of the late 20th century. There were games, history, information, and — my favorite made-up word — edutainment. The latter mostly described titles that mixed education with fun and were designed for children. (Pajama Sam was a perfect example.)

I amassed my formidable collection when I oversaw PC Magazine’s popular Top 100 CD-ROMs features. For a time, my young children and I used quite a few of these discs. Eventually, they grew out of them, and my Windows systems essentially did the same.

Over the years, Microsoft’s done an impressive job of grandfathering old software, but there are limits. Today, most of my CD-ROMs no longer run on Windows 10, even in compatibility mode.

The Collection. Photo: Lance Ulanoff

Granted, I don’t want to run all these titles. Those like Phone Disc (a digitization of the world’s white pages phone books), Encarta (a pre-Wikipedia digital encyclopedia), Microsoft Cinemania (movie database pre-IMDB), and DeLorme Map ’n’ Go (a frozen-in-time map and directions CD-ROM) have little use in our GPS-enabled, Google-ready, and mobile broadband, smartphone world.

There are, however, 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, that I was desperate to run again. Windows 10 has no interest (or ability) in these.

Technology (and the nerds who love it), however, finds a way.

It’s virtual

The best way to run old software is not by jury-rigging your current operating system; it’s by running it on its native OS. To do that, you must create a virtual machine within your current operating system.

Virtualization, the ability of one operating system to, with sufficient space and memory, host another, is as old as computing itself. Today there are a wide variety of virtualization options, including Parallels, which lets you run Windows on Mac (as does Apple’s Boot Camp) and Microsoft’s Hyper-V for running different versions of Windows on a modern machine.

Virtualization is not only useful for running one operating system inside another, it’s also a safe way of testing out software, creating a sandbox that keeps the activities of the virtualized software and applications loaded into it separated from your host system.

I’ve been aware of virtualization and virtual machine software for years but never had much use for it until now.

The basics

I wanted to use Microsoft’s Hyper-V, but even though I enabled it on my computer, I couldn’t suss out how to run it. Understand that running the virtualization system is only one part of the equation. I still had to figure out how to get an entire OS loaded into these systems.

Oracle VM VirtualBox’s main interface

Online I found extensive praise for Oracle VM VirtualBox, a free utility that looked relatively straightforward. Installation was easy, but the name is apropos. The software is an empty box; you add the operating systems.

Oracle VM VirtualBox is a rich program, but it also manages to keep things simple enough that I think anyone can build a virtual machine. There are big, colorful buttons for adding, managing, and deleting virtual systems.

Windows XP inside Windows 10.

To add an OS, you need a disc image (you can often find OS ISO files online) or original media. In my case, I’m fortunate enough to have a few copies of various Windows iterations, including Windows 7 and Windows XP. (Sadly, no Windows 95 or Windows 3.1.) VM VirtualBox even lets you choose to install 64-bit versions of operating systems that were developed before the age of consumer-grade 64-bit CPUs (Windows XP and Windows 7).

Installing these virtual machines, however, turned out to be the easy part.

Missed connections

The key to a successful virtual machine experience is not just getting that classic OS installed on a modern computer, it’s being able to reach from your gleaming present into the pixelated past through modern drives, folders, and ports.

It’s worth noting that while these virtual machines do eat up space on my host machine, they have no noticeable impact on my system performance. If you enjoy hearing the iconic Windows XP and Windows 7 launch and shutdown tunes, then the trade-off is worth it.

Since these decades-old operating systems weren’t designed to support high-resolution screens, they open in relatively tiny windows. Oracle VM VirtualBox supports screen-scaling, which allows you to expand the OS to full screen. The first time I did this, though, I lost access to my host system and had a mini panic attack.

Once I reassigned my host control, the panic subsided.

The default key combination for returning access is the right Ctrl key. My Surface Type Cover Keyboard doesn’t have a right Control key. I eventually regained system control and then, thanks to one of many useful YouTube videos on using the Oracle software, found that I could reassign my host access key combo.

Even though I successfully installed Windows 7 and Windows XP virtual machines, I couldn’t access the CD drive I used to install the OSes. My workaround was to try dumping the contents of one of the classic CD-ROMs onto a host folder and see if I could access that space via the virtual machine.

I quickly learned that the only way to access host drives and folders is to create shared spaces. I found another YouTube video that showed me how to set up shared folders and drives (including whether they would be readable and writable). Even with this access, though, I couldn’t install any of the CD-ROM files.

The solution, it seemed, was to recreate the entire environment and try running and installing these applications from the CD drive. That wouldn’t be possible until I figured out how to enable USB port access in my virtual machines.

Turned out I didn’t have all the necessary software. According to this YouTube video, I had to install a VirtualBox extension file (one I quickly found here) that soon gave my Windows XP and Windows 7 virtual machines CD drive access.

Let’s play

What I achieved is a qualified success.

As I hoped, some titles like Monty Python ran just as they did when first released in 1994. It was as silly, non-linear, irreverent, and entertaining as it was 27 years ago. I even got Python founding member Eric Idle excited about it.

Once considered cutting edge, A.D.A.M. (Animated Dissection of Anatomy for Medicine): The Inside Story, looked positively quaint with its crude 256-color illustrations and fig leaves over private parts (which you can choose to remove).

A.D.A.M. is still pretty cool.

Muppet Treasure Island wouldn’t run on Windows 7 or XP and 1996’s Muppets Inside ran on Windows 7 but haltingly, at best.

Star Wars: TIE Fighter (1995) ran on Windows XP but with no sound. This was a relatively common occurrence as the classic apps looked for Sound Blaster cards and couldn’t access modern, integrated audio systems.

There were, in truth, a lot of crashes and weird messages, like all the CD-ROMs that demanded at least 256 colors even though my system could offer millions.

An old favorite that still runs like a champ.

Quite a few of my classic CD-ROMs, like Duke Nukem 3D, ran best in DOS, which meant using the command screen, essentially the DOS hidden underneath Windows XP.

There are still many CD-ROMs I couldn’t get running on either platform, including Star Trek’s Interactive Guide and Pitfall!

Some titles took a bit of sleuthing to get off the ground. Wing Commander IV, a barely disguised Star Wars knockoff starring Mark Hamill, appeared to freeze each time I launched it. It took me a while to realize that the only input it recognized was from my arrow keys and imperfectly, at that. (I never knew which title would recognize my mouse or trackpad and which would demand keyboard controls.)

Oh, hey, Mark Hamill (in ‘Wing Commander IV’).

When the cinematic, choose-your-own-adventure style game did run, the sound was out of sync and the video stuttered. The arcade-style mission game offered more key controls but was still impossible to play. Even so, it was a hoot to see a young Mark Hamill and Tom Wilson (Biff from Back to the Future) mix it up.

Some of my old titles may never run again. These virtual machines are imperfect replicas of defunct operating systems, without full access to or understanding of their hosts’ hardware. I think that disconnect is what breaks some of the more finicky CD-ROMs.

On the other hand, I’m not ready to step off this digital walk down memory lane and plan to keep trying to review our CD-ROM history.

Tech expert, journalist, social media commentator, amateur cartoonist and robotics fan.

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