After getting a favorite old game running yesterday, I got nostalgic for other old shareware titles we used to enjoy. The best place to find them? Archive.org
From their website:
The Internet Archive, a 501(c)(3) non-profit, is building a digital library of Internet sites and other cultural artifacts in digital form. Like a paper library, we provide free access to researchers, historians, scholars, the print disabled, and the general public.
What this means to us, is a great resource for all kinds of cool old internet and related stuff!
The link above, is to their software archive landing page, however I also spend a great deal of time in their OTR or Old Time Radio section as well. I grew up listening to great radio shows like the Lux Radio Theater, X Minus One, The Mel Blanc Show, and dozens of other wonderful old programs.
Back to software, give a browse through their extensive collections, and you may find an old favorite that you can run under either WINE, DosBox, or VirtualBox