GameTrailers (GT)'s web site has a collection of videos on various video and computer games. There are histories, facts, etc.
Gaming History Source's YouTube video channel has a ton of "Let's Compare" on old video games on various (system/port/platform)s. It already has video playlists for each year
MicSauce's Reddit comment mentioned an old Wired article showing "Interstellar 8-Track: How Voyager's Vintage Tech Keeps Running ... Launched in 1977, the probe is vintage space hardware. At more than 36 years old, or roughly a millennium in computer years, it's an impressive feat to have the spacecraft drifting through the material between stars. Looking at the machine's specs is a reminder of how far electronics have come in the intervening years..."
Vintage Computing and Gaming shared Jason Scott's blog titled 5/"Five Unemulated Computer Experiences" -- "While I and many others work to turn the experience of emulation into one as smooth and ubiquitous as possible, inevitably the corners and back alleys of discussions about this process present people claiming that there are unemulated aspects and therefore the entire project is domed.
Idoiocracy's Reddit re(ply/sponse) mentioned his The Making of Games' alphabetical index of all submissions with many links including videos.
VideoSift shared an amusing four/4 minutes YouTube video showing "Ballad of a WiFi Hero ... animated adaptation of the famed McSweeney's Internet Tendency piece, 'In Which I Fix My Girlfriend's Grandparents' WiFi and Am Hailed as a Conquering Hero...'"
MacWorld (United Kingdom (UK)) -- "The Macintosh launched 30 years ago on January 24, 1984. The world was a different place back then. To give you an idea of what the world was like that year, here are a few other things that are turning 30 or celebrate their 30th anniversary in 2014..." and "Mac turns thirty on 24 January. For a glimpse into 1984, here are some other things turning thirty, including plenty of tech from Flash to Facebook's father..."
This xkcd comic strip shows what your overlord's computers are like like the one on Friday morning PST. :/