I like the South Park movie. Team America is ok.
I haven’t watched many movies for years but recently enjoyed some about finance, particularly The Big Short. I also found Wolf of Wallstreet and Boiler Room worth watching.
I watch more YouTube and reality TV shows. IME it’s hard to find educational stuff that I can learn much from outside specific niches where people have expertise like chess or a video game. I generally like realistic stuff more than scripted, e.g. Life Below Zero, Big Timber, Outback Truckers or Mountain Men show parts of life I don’t see otherwise (those aren’t esp important things to know about though). Teen Mom 2 and others with relationships and drama (e.g. The Bachelor, Love is Blind, Married at First Sight, Marrying Millions, 90 Day Fiance) can show stuff about how people’s lives suck and how they view relationships, so I think it’s good to see a bit of that to have some familiarity. There are things like How It’s Made, Impossible Engineering and documentaries that have nice info. I also sometimes like historical fiction, esp for Greece or Rome, but anything that’s more about history rather than putting modern drama or comedy in an old setting.
The Pickup Artist (2 seasons on vh1, around 2007) was the best reality TV show I’ve seen. Bullshit was a good show.