I'm reminded of the awesome youtube channel Pixelmusement with the "Shovelware Diggers" series that's been going on for a few years. Basically they're exploring the contents of a 2 disk CD Shareware set and more or less trying to run/play/review the 2000 programs on the disks.

It's a fantastic snapshot in time of the pre-internet CD-ROM era.

https://www.youtube.com/user/Pixelmusement