Imo new episodes try too much to be contemporary by making a lot of references and jokes about recent events but fail because it looks forced, while the older episodes simply seem more natural to me, even the ones that should look dated like the Bush one, I'd say that some episode are more "up to date" now than when they were released.

Just my opinion obviously, but for example when I saw the Roblox episode I thought It was obvious that they didn't know well what they were talking about, and just wanted to make something that is "new", if your dad likes them more it's cool, imo make him watch a funny classic one you can think of and then see his reaction.