1. The Wolf of Wall Street (2013) and The Great Gatsby (2013)
These are two different stories of wealth’s abundant, yet corrupt pleasures. Both movies show the harmful effects that being excessively rich has on the human soul.
Wealth: 10+
Creepiness: 2
Fun: 9
2. Arbitrage (2012), Wall Street (1987), Too Big to Fail (2011), Margin Call (2011), and The Godfather, Part II (1974)
What’s more entertaining than a film about earning a fortune? Well, there’s one problem: making money can be quite boring IRL. So, in movies, we often see criminal affairs that are added to spice things up. These movies tend to follow big events, for example, Wall Street premiered only three months after Black Friday in 1987. And after the 2008 collapse of Lehman Brothers, such films as Margin Call, Arbitrage, and Too Big To Fail were shot. But the winner in capturing the chief executive’s isolation is The Godfather, Part II. This series began after the oil crisis of the 70s.
Wealth: 6
Creepiness: 7
Fun: 2
3. Trading Places (1983), Cinderella (2015), and Limitless (2011)
The classic trope from rags to riches is timeless. Movies like Cinderella and Limitless show characters make sufficient gains, but it’s never straightforward and easy. That’s why we worry so much about Eddie Morra who is running out of NZT-48 pills. And of course in the end the movies actually allow the characters to keep their wealth. In Trading Places characters Louis and Billy Ray dupe rich financiers, and in the end, they relish their enormous amounts of money.
Wealth: 7
Creepiness: 0
Fun: 10
4. American Psycho (2000)
He’s handsome, he’s smart, and he’s an insane criminal, of course. Patrick Bateman in American Psycho makes us think about the rich and morality. What are they hiding and how far is too far for them?
Wealth: 9
Creepiness: 9
Fun: 2
5. Robin Hood (2010), The Hunger Games (2013), In Time (2011)
These are the films that show class inequality and the elite’s carelessness about lower-class conditions. This has been done in the form of fantasy fiction (In Time) or a fairy tale classic (Robin Hood). But The Hunger Games series comments on this most notably.
Wealth: 8
Creepiness: 7
Fun: 3
6. Marie Antoinette (2006)
What can make a movie where the wealthy watch their inferiors being killed for their own entertainment even more disturbing? Only the fact that it’s based on historical truth, which is the case of Marie Antoinette.
Wealth: 10
Creepiness: 4
Fun: 8
7. The Philadelphia Story (1940), Goodbye, Columbus (1969), Love Story (1970), and Cruel Intentions (1999)
America has its stories about old money. In these movies, the only goal of rich parents is to make their daughters marry other rich people instead of the funny lovable men that these female characters are falling in love with. Movies mentioned above all invoke this taboo.
Wealth: 6
Creepiness: 1
Fun: 9
8. The Silence of the Lambs (1991), The Devil’s Advocate (1997), Indecent Proposal (1994), and All Good Things (2010),
In these movies, the wealthy are portrayed in the creepiest way possible. There are a few somewhat realistic films like All Good Things, which shows Ryan Gosling’s character as a reckless murderer, and some boring morality stories such as Indecent Proposal. The Devil’s Advocate and The Silence of the Lambs are straight-up horrors, but the good ones.
Wealth: 6
Creepiness: 10
Fun: 0
9. Ferris Bueller’s Day Off (1986), Clueless (1995)
Wealthy people are just like everyone else; they, too, have to go through awkward periods in their young years, the only difference is that they have a credit card (Clueless) or a Ferrari of their dad (Ferris Bueller’s Day Off).
Wealth: 9
Creepiness: 0
Fun: 10
10. Scarface (1983), The Color of Money (1986), and Casino (1995)
There are so many movies out there that show people who want to be wealthy so bad that they couldn’t care less about laws. Do we really think there’s a great crime involved when it comes to great fortune? No one knows. It gives us such great movies as Casino, Color of Money, and Scarface.
Wealth: 3
Creepiness: 7
Fun: 10 in the beginning, 0 by the end
