Can you think of any instances where powerful tech companies broke laws, perhaps in ways that increased profit?

I can't think of any. Thankfully, we are saved.

tries to think .. 67 .. sigma rizzler .. AI cats dancing .. hehehe .. gives up .. yeah no. nothing comes to mind

I think in social media and search, clear ad labeling laws exist and are also enforced. I can imagine that OpenAI will be under a lot of scrunity and it will be easy enough for outside investigators to prove how ads are served and if it's are done illegally (e.g. by creating an ad account and then testing how their ads are served).

Will they still try to skirt the laws? Of course.

I'm guessing one form it will take is simply by omission.

User asks for recommendation. AI generates answer saying product is absolute garbage. Company pays to simply have that portion of the answer just not appear. It will be a post-filter sentiment analysis on the original answer. Nobody can ever prove what would have appeared or not.

This is the beauty of AI - while a search engine is at least semi deterministic and you can reasonably question why it wouldn't bring up a site that is clearly relevant, AI has plausible deniability. who can ever say why it generates this answer or that?

A subtler form would be to associate (dis)favored topics with (un)happy ideas, so that wrongthink is implicitly punished with depression.

Where?

In the US.

There's a big world out of US you know?

And in the EU.

Yes, I know. I thought you were asking where do ads need to be labelled as such, and I gave an example.