Your old school overlord is basically like this old living dino(saur) Dilbert comic strip. :P
This over two months old Dorkly comic strip showed "The 9 Greatest Fears of Gamers".
HardOCP shared a funny/hilarious/silly five minutes and 27 seconds YouTube video titled "Johnny Express" -- "It's 2150. There are all sorts of Aliens living throughout space. Johnny is a Space Delivery Man who travels to different planets to deliver packages. Johnny is lazy and his only desire is to sleep in his autopilot spaceship. When the spaceship arrives at the destination, all he has to do is simply deliver the box.
Grickit's Reddit comment mentioned Adult Cat Finder that is a funny web site to "Find Hot Local Cats in YOUR AREA -- Are you having a hard time finding local cats in your area? Do you wish there was a way to connect instantly with one online, at any time? Now you can! With Adult Cat Finder, you're never more than one click away from chatting with a hot, local cat in your area! ..."
Idoiocracy's Reddit re(ply/sponse) mentioned his The Making of Games' alphabetical index of all submissions with many links including videos.