GameSpot has a YouTube playlist showing fifteen/15 videos showing "Video Game History Month 2011" to "celebrate Video Game History Month with a sampling of the people, hardware, and events that made the industry what it is today."
YouTube has a channel titled "Factual Game Facts About Facts" with short animated skits/sketches, with cussings and not for young/sensitive viewers -- "...
This amusing Dorkly comic strip shows "Gaming Then & Now".
This totally fits your old overlord's gaming history. ;)
This three pages Dorkly article shows "The 15 Most Frustrating Situations in Videogames".