His name is Corbin Davenport and before you ask yourself, 'Self, why would someone go through the trouble of porting Windows 95 over to a tiny, underpowered smartwatch display?,' perhaps the better question to ask is, 'Why not!?' Granted, the usefulness of such a hack is certainly something to question, but it's all in good fun. It also underscores how far technology has advanced since Windows 95 was in the driver's seat many moons ago.
In his YouTube video, Davenport notes that he got Windows 95 to run on Android Wear using aDosBox, a free app that's available to download on Google Play. It's not ideal, but when it comes to porting Windows 95 onto Android Wear, there aren't exactly a bunch of options.
Be that as it may, Davenport does indeed get Windows 95 successfully up and running on his Gear Live, though not without some wonky behavior. It's easy to navigate the menus and desktop in Windows 95 using touch input on the Gear Live, but if you try to run an application, it will crash due to lack of RAM. Samsung's Gear Live actually boasts 512MB of RAM, but aDosBox wasn't written for this sort of thing - bummer!
Still, it's a pretty nifty hack, and if you enjoy stuff like this, check out Davenport's other YouTube videos. He has a couple of similar videos, one of which shows Doom running on Android Wear and another with Minecraft PE running on it.