Allow me to clear something up. This isn’t “most evil billionaires.” There are plenty of evil billionaires. Some of the men listed here are evil; some are not. That’s not the criteria.

This list examines all the wealthy men who aren’t enjoying themselves, those who are just as miserable with the cash as they would be without it. The anti-Thomas Crowns. The anti-Arthurs. These guys largely live to work, and have nothing to show for their riches but some nice suits and a frown. You won’t find Montgomery Burns, Gordon Gekko, or Lucius Malfoy on this list. They have way too much fun being evil. This is for the guys that wealth is just wasted on.

Nicholas Van Orton – The Game

Growing up rich doesn’t mean you’re growing up happy, and the odds of being well-adjusted are even less so if you happened to pull up and watch your dad take a header off of the roof of the family estate. Thank God for CRS. With a sequence of elaborately-staged run-ins and scenarios, CRS creates a terrifying ordeal that allows Nicholas the opportunity to figure out what life is like. It helps that there’s a hot girl to fall in love with as well.

Van Orton manages to both talk down to people while at the same time treating them with the general misery that an employee at the DMV would project. All the monogrammed shirts in the world won’t brighten his day.

Jeffrey Lebowski – The Big Lebowski

I happen to like Jeffrey Lebowski, if only because when I get rich, all I want to do is bitch and treat Phillip Seymour Hoffman like shit. Sure, it’s not the most fulfilling life, but it’s what I want to do. However, I would totally expect to be called “joyless” much as I’m calling out The Big Lebowski as being such.

I wish there were more scenes with Jeffrey and his wife Bunny. I bet he just treated her like crap all the time. I don’t know her very well personally, but I can’t imagine that Tara Reid is a magical cure for depression.

Sure, he’s in a wheelchair, but you would think that even a miserable, incapacitated septuagenarian would be able to delight in belittling Tara Reid.