Well the only way a 20 year old is getting weirded out by a Win 95 interface is (1) he has never seen a Windows machine because Win 10 basically reverted to the same Win 95 interface or (2) never worked on a desktop/laptop with KDE, Cinnamon or the other DEs inspired by Win 95. And Win 95's UI rocks IMHO (and I say that as a person closer in age to those annoying pipsqueaks in that video). You go to a button labeled "START". It has clearly labeled folders called "Accessories", "Programs", "Internet" etc and then you get to where you want to. For 90% of the UIs, a tree like that is a perfectly good data structure.
The more annoying thing is why is it that software like Office etc take two orders of nagnitude more RAM while being essentially 90% similar in functionality to Office '97