The first one is actually Japanese and the second is an independent production. Sure, it was not unheard of. But I think the Simpsons is what made it mainstream. My point was that adults were not sitting down in front of the TV to watch cartoons (and specially not ones based off of a video game). That was associated with kids.

> The first one is actually Japanese

Yes, I know. I don’t see how that’s relevant (other countries do exist and matter) but it’s because I thought you might nitpick that I added a USA example.

> and the second is an independent production.

I don’t see how that’s relevant. It was a worldwide hit and is an important piece of movie history, it’s not an obscure college movie.

> Sure, it was not unheard of.

It’s considerably more than “not unheard of”, I specifically chose well-known authors with well-known works. Ralph Bakshi alone directed eight adult-oriented feature film animations before the Simpsons was a thing. Those are far from the only examples.

I don't have a stake here, but one should definitely differentiate between a full featured adult animation which ran in the cinemas and sometimes on TV, just like a regular films (and in 03:00 AM block), and a syndicated, every week, for years, animation running when the kids are already in the bed but you still sit on couch with a half killed six-pack.

The Flintstones were on television, in a prime-time slot, three decades before the Simpsons. Wikipedia lists more North American adult TV shows from before 1990.[1]

The Simpsons are important in the history of animation, but however you look at it they were definitely not the first to explore animation for adults. They weren’t the first in their own country, nor were they first on a regular non-kids schedule on TV, nor were they the first successful case.

[1]: https://en.wikipedia.org/wiki/List_of_adult_animated_televis...

Oh wow, I completely forget about Fritz the Cat. I read those comics as a kid/teen (presumably the German version) :D