A lot of the jokes in last week tonight don't exactly land when they originally air either, but that has more to do with the writers than available context. I

A lot of the jokes in last week tonight don't exactly land when they originally air either, but that has more to do with the writers than available context. I run into this problem not just when watching old shows, but also when watching contemporary TV developed in other countries. Usually it's references to proper nouns I've never heard of, and I do often look those up, but even once you know what or who something was sometimes you'd have to be willing to go deep into various rabbit holes to really understand it.