I can second the Noah Caldwell-Gervais recommendation, though I watch his videos in chunks when I do watch them. I also don't always agree with his ideas on gameplay and mechanics, though he and I are on entirely different wavelengths when it comes to that topic, but he still has interesting things to say. He does do entire franchise videos at once, though.
Raycevick has a lot of "...years later" videos. His videos on all of the Halo games up to Halo 5 are probably what propelled his Youtube channel into the stratosphere and they're really good. He dives into the circumstances surrounding each game's development before really diving into those games, which is probably something more in line with what you're looking for.
There's also NoClip, for a Youtube channel devoted to video game documentaries and probably way more in line with what you're looking for than either of the previous recommendations.
For something more along the lines of critical thinking, I'd recommend Errant Signal. He doesn't put out videos as often as most - I'm pretty sure he holds down a full time job and Youtube is just a side gig - but when he does it's usually some great food for thought.
Go diving into GDC talks. There are a lot of videos of developers themselves talking about the games they've made, the challenges presented, and how they overcame them (or failed to overcome them and learned from their mistakes).
Ars Technica has their "War Stories" series, which are good for bite-sized videos describing general issues and how they resolved them, but I haven't often found them in-depth enough to be satisfying. Just some interesting tidbits.
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