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.