Yesterday I was faced with a tough decision, one which could have had serious consequences. Should I delete some old Firefox installers from nearly 10 years ago (version 2.0), from my collection of downloads that had been building up (a few thousand different applications, mostly freeware stuff which I might have used once and uninstalled in 2008). I keep these on a 32GB USB drive so I can quickly go to another machine and install something
Would I ever need to install a new browser when I had no internet connection to download one? Yes, I work with some PCs which have no internet connection but still need a browser to configure switches, routers etc. (and IE is an older version than we need) but outside of work, probably never.
There is always OldVersion.com which has more old software than you would ever need, including stuff which wouldn't even work if you installed it as the servers (Windows Live Messenger etc.) don't exist any more.
I like to think I could have the files ready to sort out a PC running anything back to about Windows 98, if anybody I knew had a problem with it but I can't even think of anybody using XP now outside of a business.
There is still plenty of software for Windows which was released over 10 years ago that is still usable (including in Windows 10), and what might been seen as bloatware with pointless features back then is now pretty lightweight compared to the latest version and does just what you need it to do (MS Office 2003, Adobe Reader apart from the security issues).
Here are two of the oldest downloaded applications I still have (both files dated 20th September 1999). Both installed and running in Windows 10.
Real Producer G2
Remember Real Audio? The very low bitrate codec which could be used to stream over a dial up internet connection? The one where you were locked into using Real's own software to do anything?
At the time I hadn't started collecting or ripping my CD music in mp3 format. Real Producer was handy for recording radio shows off air as it could record directly to disk at 20kbit/s (only 10MB per hour) at listenable (better than AM radio, about 10KHz mono audio bandwidth). I think my PC at the time with its 187MHz CPU would be struggling to encode mp3 in real time so Real Audio was pretty good in that way.
Article about Real Producer G2 from 1999
I didn't find a download link for this (even at oldversion.com) but there is still a Mac version (for Classic Mac OS) at Tucows.
The File Splitter
At the time, this was a very useful application. If it wasn't for this, I wouldn't have Real Producer as I had to split the download to fit it onto floppy disks to get off the PC in the library at uni. This was before CD writers were standard, and 9 days before I bought my first CD writer for £200.
The application is still available to download (last version 1.31, released in 2005)