The show with kids asking wall street types about why they're bad people was Wonder Showzen. It was on MTV (or 2?) during their animation phase. Being slightly edgy was their attempt to get views from college kids.
I'm not aware of anything other than works by commies in less reactionary countries that are truly radical, like they relate your current situation to organizing for revolution explicitly enough that it is understood as such. It's important to understand that liberals don't really understand the obvious metaphors for left action and organizing, they are too ignorant of what to recognize.
For example, Sorry to Bother You is a radical movie that uses (great) ham-fisted metaphors in a near-future environment and the liberals still didn't get it. Liberals also didn't get most of the movies/shows I'll list at the end.
I think movies that were more direct would simply not get produced, or at least not most of the time, for a host of reasons: (1) it doesn't slot into producers' cookie cutter ideas of profitability to explain anti-capitalist revolution in real rather than cartoonish terms, (2) producers are ideologically capitalist and will balk at a direct criticism that they understand and think could produce a credible threat to themselves or their idea of themselves, (3) there are too few people with established careers that want to make this content, the industry (and society) already selects for the intentionally bland or liberal.
Anyways we do have some decent radical media just with that caveat that liberals don't get it because they're politically ignorant.
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Sorry to Bother You
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Andor
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Snowpiercer
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Parasite
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Okja
The above movies aren't even the usual Hollywood appropriation of leftist themes that have been so divorced from context that they become bland and in support of liberalism, e.g. being the collectivist "underdog" fighting "the oppressor". They smack you over the head with revolution due to anti-capitalism and/or an imperialist entity. Andor has parts literally modeled after the life of Young Stalin. And the liberals still don't get it. They require explainers in their media sources to relay its meaning to them and those explainers also usually don't really get it.
I think that if we want radical media that appeals to the masses we should do everything we can to educate the masses so that they recognize and understand what it means to be radical. That it's not an aesthetic, it's an analysis and opposition to capitalism and there are patterns and schools of thought and it is very relevant to their daily lives.