ROMEO IS A DEAD MAN is proving to be fun but somehow raises the question of "what the fuck is going on and why do I vibe with it?" even more than previous Grasshopper games. Why does the FBI have a space time division that flies about in a time travelling spaceship with a massive wave motion gun on the front? Why has your family come along for the ride? Why do zombies grow from seeds on a farm? Why is your grandpa embroidery now? Why is a senior FBI agent a cat? Who is storing their spices in meteorites? Is the screen currently black because of a bug or is it an artistic decision? (It was a bug)
The biggest question it raises for me though is why there seems to be a generation of Japanese game developers obsessed with videogames as a medium - whether it's switching controller ports in a fight, changing gameplay to a text adventure for dream sequences, or the main character fast forwarding through the villainous monologue, there's a self awareness to their games I don't see elsewhere. They don't just give a nod and a wink to the 4th wall, they aggressively try to pull the player through it to interact even more directly with the gameplay and story. What happened to make them like this? Is it some part of their cultural experience or a formative piece of media? Or are they just a set of weirdos that coincidentally happened to be born relatively nearby?

Every piece of media has its auteurs who try to do the most they can with the format.

Suda51's MO to all those questions is "Who cares as long as it's fun"

I can't offer anything other than armchair hypothesising, but Tezuka Osamu, the most important person when it comes to making manga and anime what it is today, and whose influence can also be felt in video games (e.g. Mega Man clearly taking influence from Astro Boy), liked to do things like having a character rip out the gutter between panels and break it in half in a fit of anger. So these kind of meta-hijinks have been part of modern Japanese popular media since the beginning.