If you really want the Windows 98 experience, you can always turn your resolution down to 800x600 (or smaller, if you can) and do: Right click on My Computer,

If you really want the Windows 98 experience, you can always turn your resolution down to 800x600 (or smaller, if you can) and do: Right click on My Computer, Click Properties Select the Advanced Tab Click Performance Select "Adjust for best performance". That sets the most obvious appearance to something akin to Windows 98. As far as things just "working" I have yet to use a system that is as good in that aspect as Windows 7 (and Vista before that). The problem of things not working doesn't lie in the OS, it's almost entirely for the crap we consider "working" now, that wouldn't have even been thought of now. As an anecdote, a year or two ago I acquired an old Windows 98 machine, which I played around with for a few hours. After fighting with it to get all of the drivers found. This was a fresh installation, on Windows 98 era hardware, and I ended up having to install a floppy drive into my desktop, find some floppies and go out and download each of the drivers for everything to even get it working. Once I finally had it up and running, I decided I would try and go online. The only site I usually go to, and could get to an even usable state was GMail, through the "Low Bandwidth" version. The problem isn't with the OS. Its all the crap we try and do on computers, and how shoddily that is put together. If you want to see it for yourself: Go out and get a copy of Windows 7 (Get a 90-day trial: http://technet.microsoft.com/en-us/evalcenter/cc442495.aspx http://technet.microsoft.com/en-us/evalcenter/cc442495.aspx) and go install it on a VM. Disable networking, and try and use it like you normally would. Install the minimum applications you need to do your work. You will be amazed at how things "Just Work". Then try and go online for a few days on it, and watch it DIAF.