Succession, Parasite, The Joker, Mr. Robot, How to blow up a pipeline, The Edukators… Would love to hear about more
Arrested Development
TV - Loot, Fall of the House of Usher, White Lotus
Movies - Triangle of Sadness, Glass Onion
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Schitt’s Creek comes to mind.
There are already a lot of good suggestions here!
I would add Eat the rich and The menu (not related) for movies criticizing the rich. Although the former just makes fun of them.
I would also argue for Andor even though it doesn’t focus on the super rich and instead on the rebellion and the people making up the cogs of the fascist imperium. It still shows the rich in a critical light. I haven’t seen any series that made me want to fight the system more than Andor.
Altered Carbon season 1
It’s a shame only one season exists, right?
What a shame, so much wasted potential
Righteous Gemstones if you want to focus on uber rich televangelists, specifically
There Will Be Blood. The acting is brilliant and you see the MC going from a poor miner to his own oil empire, showing just what sociopathic chameleon he is at many points. It’s longer than average, but it’d sure keep you engaged. I see it as a modern-made epic story that pretty much describes what (self-built) multi-millionaires are like.
In Time
Silicon Valley
Triangle of Sadness, The Menu
Highly recommend both of them
TV: The White Lotus
The good fight, but it’s a bit on and off. There are subplots about resistance movements, but it’s more against far right than rich. They are just aligned. Some is the imbalance of justice.
Anything cyberpunk usually fits that bill. Like Captain Laserhawk: A Blood Dragon Remix sounds and is ridiculous in many ways, but also has some insights on the rich taking over the media and prison system.
“Killing It” on Peacock was a surprisingly dark comedy about the death of the American dream.
Been a while since I’ve seen it but a movie called “A Day Without A Mexican” where rich assholes and middle class white people lose their nannies and field workers picking their food. I believe it was a dark comedy but like I said been a number of years since I saw it…
Leverage is one of my favorites. The reboot is pretty good as well.