Defying the laws of Common Sense™, I have created some virtual machines with VirtualBox 3.0.8 to run Windows 95 OSR 2.0, Windows 98 SE and Windows Me. There's no practical use for them whatsoever, except maybe testing how good modern websites look on old operating systems and browsers or something, or pushing the emulator/virtualizer to its limits, out of the "safe area".

The thing is, they actually work, to various degrees:

• Windows 95 OSR 2.0 cannot run with hardware (AMD-V) virtualization enabled; otherwise, it will halt the system complaining about a "Windows protection error" when loading some component.
• Windows 98 SE works somewhat slowly in software emulation mode, and crashes very frequently during the boot process when using hardware virtualization.
• Windows Me is unusably slow in software emulation mode; however, it works mostly fine and fast with hardware virtualization enabled, bar some occasional boot-time BSODs.

The network card drivers included with each one work just fine, out of the box even, except that Windows 95 OSR 2.0 doesn't install the TCP/IP stack by default and it's necessary to add it by hand with the Network control panel. And we are talking about software that included Internet Explorer 3, forcibly preinstalled even.

For the video controller I am using the VBEMP x86 driver for Windows 9x (more specifically the 2008.10.21 build) which supports extended graphic modes, up to 1600x1200 with a color depth of 32 bpp. It is mostly stable if not a little slow for some operations, especially when running without hardware virtualization; reducing the color depth and/or resolution should help. The only major problem I have spotted so far is that the screen gets garbled when opening a command (DOS) prompt, but that is easily solved by switching the prompt's fullscreen mode a few times. It also happens at random times when running Windows Me because of some stupid background process that runs from time to time with a minimized console; in such cases, I use CTRL+ESC and then R to bring the Run dialog and start a DOS prompt (command.com) from there and toggle fullscreen mode as required.

It goes without saying that performance may be increased by disabling some features such as window animations, showing window contents while moving, etc.

There's a somewhat detailed tutorial on the VirtualBox forums about running Windows 9x as well, but I didn't follow it, and I found about the VBE drivers from a qemu-related FAQ instead.

Obviously, this is just experimenting with VirtualBox a little too much, and for real work it's better to use Windows 2000 or XP instead. The main motivation for trying these operating systems in it despite Sun's recommendations is that qemu's Cirrus Logic emulation has gone downhill ever since 0.10.0, making the VBE drivers almost a requirement, and the introduction of a resizable window frame in 0.11.0 is more a bug than a feature for me. It is only annoying when running operating systems in resolutions greater than what my KDE 3.5 setup supports because it doesn't play nice with KWin, and when the window gets resized there's no apparent easy way to get rid of the blurry appearance.

I'm not trying VirtualBox 3.0.10 yet since there are no changelog items of my interest at the moment; it's a fairly large download after all.

UPDATE 2009/11/07: updated to 3.0.10, no new problems with Windows 95 OSR 2, 98 SE or Me so far.