LGR, or Lazy Game Reviews has occasional retrospectives on the same era of PC gaming that Ross covers. He also puts out videos about hardware and various bits of PC history, which can be interesting if you have that sort of interest. I don't typically enjoy his straight video game reviews - there are better channels for that - but his knowledge of the industry and the most historic games in PC history is top notch.
ClementJ64 and KingK both also do gaming retrospectives that aren't particularly in-depth, but I like hearing their opinions and experiences with some of my favorite titles. Clothmap is a bit different - Drew Scanlon, formerly of Giant Bomb, travels around the world, lecturing about culture and entertainment through the lens of gaming. Sometimes video games, sometimes tabletop or card games, sometimes sports. You may know Yahtzee Croshaw from The Escapist? He has a long-forgotten solo YouTube channel where he and a friend of his talk over a ton of old PC games from the 80s and 90s; mostly adventure games.
For movies, I assume you know about Red Letter Media. I also enjoy Welcome to The Basement for retrospectives on movies from the 70s, 80s, and 90s. Their general concept is that two guys watch a movie together. One of them has seen the film previously, and the other hasn't. They compare thoughts and opinions and crack jokes along the way. It's hit or miss, but generally good for something to watch when you have nothing else. I also love Folding Ideas - a film maker that talks about the technical and artistic skills of film making by looking at popular movies and picking apart what they do right and wrong.
There's also this massive playlist of Long Form Analysis videos, with various folks talking at length about music, movies, games, books, and just about anything.