I talk about cultural references in games (and movies, TV shows, books, etc.) and how they make those games feel dated.
Cain wants to talk about why he hates cultural references. Almost said it was just about games, but really he hates them in general.
When Cain says cultural references, he doesn't just mean you referencing a song or movie you like, but any form of pop culture. Famous people, events, etc. Thinks Fallout 2 went overboard with them. Fallout made references to cultural events, but almost everything they had that was super obvious was a random lucky special encounter, that left the rest of the game feeling more timeless. Glad New Vegas hid that stuff behind Wild Wasteland, those who like it can get it others can avoid it.
Cain doesn't like making cultural references because it roots your game into a particular time. Cain prefers games to be timeless, by rooting he means that you have locked your game into a particular point in time that only a particular audience will get. A few years after, people might find some stuff funny but be confused why you are making a big deal about an actor or wonder if they are supposed to know who that politician is. What will happen is your tv show/movie/game whatever feels dated quickly. Cain knows that when he watches old TV shows he was into from the 80s/90s, he really preferred it when the guest stars weren't made a big deal of. There was an actor on, you kind of recognize them, if they make a big deal about it, quite possible he's forgotten who that actor is. If the actor references someone, everyone born afterwards won't get the joke. If an actor name drops George Bush, do they even know George Bush, or know which Bush they are talking about specifically? Show gets dated fast.
This dislike extends to the channel, Cain wants this channel to be timeless and avoids references. Cain wants this channel to be about game development and best practices for the audience to follow if they want to make good games, talking about the outrage of the week is not helpful. Shocking cutscenes, Sweet Baby, Brexit, misleading trailers, nobody will care about this in a few years. If you're younger than Cain, trust him, 90% of the things you think are important you won't even care about or remember in 10-20 years. The 10% you will care about, good luck figuring that out right now. You will be (un)pleasantly surprised in a few years about what you still care about and what you think is stupid. Good luck on guessing, don't try guessing, or if you do try guessing, don't make a public guess by putting it into a game you made that everyone can see. Forget years, things change so fast people might not care about in a week, or a day. Cain tries to make videos that even someone 10 years from now could find useful for their games, if they are working on a loot table his loot table video is still useful. If Cain talks about the "that cutscene with the bear", that person from 10 years will have no idea what he is talking about.
Try to have the same goal, make something people a year from now will have fun with and understand. There are many other things to consider for making a game timeless that aren't really in Cain's area of expertise but he will go over them in general; Going for super realistic artwork will always be beaten by next year's level of realism, game will look old and dated real fast. If you don't believe him, check out the realistic 90s games, particularly the FMV era which looks silly now.
If you absolutely, positively, are not convinced, and must add a cultural reference, use Cain's guide to humor. Make the reference in a way that if the player doesn't get the reference they don't even know a reference was made. They don't feel left out or that they missed out on. If they do get that feeling, they won't blame themselves, they will blame you. If you do something to make the player left out, they won't feel left out, they will just think the game is dumb.
TL;DW If you have to add a cultural reference to person/event/whatever, put it in in a way where people who know it will get the double meaning, but other people will get the surface level and then move on. If you do that, your games will last longer and be talked about longer.