How about Wally Gubbins? A series of silly skydiving videos. My father has a ton of them on VHS. I loved it as a kid. I just looked, you can even find them on YouTube. So maybe not that obscure.
In terms of software I remember having several ad games. So, games that are basically just an ad. I had a Bifi game. Some weird game about colours where I don’t remember what it was for. And a “game” about Chesterfield Cigarettes. I remember that I had to install QuickTime Player to run it. It was basically like Google Streetview when you walked into buildings with a few interactive elements put in. No idea where I got it. Might even still have the CD somewhere.
What is an obscure piece of media or videogame that you think nobody else here has heard of? (kbin.social)
It could even be a youtube video or movie that you don't think anyone reading this has heard of besides you.