This video gets teenagers to bootup an old Windows dial up PC and try to get the thing online. 13 floppy discs to load the system and hey, what's this dial-up business. http://nerdist.com/watch-confused-teens-react-to-windows-95/
I hope they found the ultimate prize...SkiFree! (Download available for a little nostalgia. Can be found at 'The Most Officialest SkiFree Homepage' Cheers!
This was the first OS that I used. But the current Windows version is still quite similar when it comes to looks, so I thought this video was kinda dumb. The video about MS DOS was more interesting.