With all the discussion spurred by the Half-Life episode and the possibility of doing a selection of Win3.1 games, I’d like to put forward a suggestion for the natural first choice.
It’s hard to overstate what a huge deal MYST was when it came out. It massively drove adoption of CD-ROM drives and was the best selling video game ever for over a decade. It was so ubiquitous that it was commonly available and played in school libraries, similar to Oregon Trail. I remember being excited to play it during indoor recess when the weather kept us inside, and the librarian coming over to watch when I got to a new area they’d never seen before.
There was a lot of discourse at the time about how MYST “killed” adventure games, but personally I don’t buy that. The genre was growing stale by the mid-90s and most of the big adventure shops eventually folded up. I’d argue MYST injected a bit of new life into the genre and kept it going a bit longer than it otherwise would have. It was also a technical marvel just as the original King’s Quest was when it first launched.
There’s a lot to say about the game, the series, and its effect on the industry and tech as a whole, so I think it would make a great first win3.x episode.