Notable/interesting/useful software that is notably old

In My Humble Opinion
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I could post in GQ and ask what the oldest piece of software is that is still being used, but I’m more interested in learning about old software that is interesting or useful today and that can still be run reasonably easily on a Windows or Unixlike (including Mac and Linux) environment.

What are some software applications that are notably old (as a rough rule, anything from before 1990 is probably notably old in the world of computers) and that are still useful or fun today on modern computers? It’s ok if the software has to be run in an emulator or recompiled from the old source for a modern processor and/or operating system architecture, as long as it’s fairly straightforward for a techie to do. I’m less interested in software such as modern versions of Microsoft Word where the history of the software itself goes back years but modern versions are, well, modern, and I’m not sure that a large percentage of the original code still remains. Emacs is interesting because it’s UI has hardly changed over the years though, so a piece of software such as that that has been updated for bug fixes and some new functionality but still seriously hearkens back to the old days is probably in scope.

Advent, the computer game, is a good example. Are there any other mainframe-era computer games that are well remembered and even played today? Is there a financial application written for the IBM PC in 1983 that is considered so good that many accountants and managers run it in a DOS box/emulator/virtual machine today, eschewing modern equivalents?

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Advent!!!

Back in the day (mid 1970’s) I spent umpteen hundred hours playing that! This was on a corporate mainframe at work, after hours – before PC’s were invented, before Apple gave us the Apple II

It wasn’t until years later that I had my very own MSDOS-based 80386 mochine, and somewhere along the way I found a DOS port of the program.

I’m sure OP knows (since it’s mentioned in the Wiki he cited), but I’ll mention it for others, that Colossal Cave is based on a real-life cave in Kentucky.

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A ton of games, especially arcade and console games once CPUs began being implemented. Space Invaders, Pac-Man, Atari titles, etc., are not only still widely available today, they’re usually used via emulation, thus preserving the original code. Midway’s Gun Fight from 1975, the first CPU arcade game, is readily available through emulation. And many of the original programs are not just used in hobbyist circles, they’re often still commercially available. I could go out and purchase arcade and home versions of Space Invaders from 1978 that still use the original code.

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NM