With The Dark Knight Rises rising on the horizon, Hollywood is abuzz with all things Batman, and under that umbrella falls the man behind the mask, Bruce Wayne. Wayne wouldn’t be the hero that he is if it wasn’t for a really shitty life up to the point he decided to don the cape, and a big part of that was being rich.

Sure, being rich affords him guys like Lucius, but it also made him miserable enough to shake things up a little. Here’s a few other guys that prove money can’t buy happiness all the time.

Now let’s talk about some rich jerks.

Nicholas van Orton – The Game

He watched his dad die, and seems to exist as some “forever alone” billionaire. He treats everyone, including his addict brother, like crap. Knock it off, NVO. You’ve got great shoes and a really nice housekeeper that makes you nice baked goods for your birthday.

Van Orton is pretty much the only guy we see who really shows promise of change late in their film. All because of the game. The game works. It changes people. But how much? I want to see the continuation of this story with Nicholas running around like a better-dressed Mr. Deeds, though that will probably never, ever happen.

Oh, to dream!

Cal Hockley – Titanic

If you’re going to be a rich jerk, then own it. And no one owns “rich jerk” like Billy Zane (“ZANE!”) playing a privileged asshole on the Titanic, a ship loaded with privileged assholes. I know James Cameron is busy making 14 more Avatar films, but couldn’t he hand off the next chapter of Titanic, aka “What became of Cal?” to a lesser director, like F. Gary Gray, or Rob Cohen?

Cal was so awesomely evil that it makes me want to punch my computer in delight. He shot Jack Dawson’s friend in the stomach, and probably displaced poor women and children so that he could live. Can’t say I argue with either of those (Jack’s friend was annoying, and I really like not being dead), but when you do those things with slicked-back hair, it takes things to another level.

Sometimes being a jerk is awesome, and Cal is just the awesomest.

Bruce Wayne – Batman Franchise

Granted, Batman’s had a tough go of it, but as far as superheroes go, he’s lacking in the levity department. I’m sorry that you were in a Nepalese prison, Bruce. I’m sorry that your name is Bruce, Bruce. I’m sorry that your parents were killed by criminals, Bruce. I’m sorry that you were terrified by bats when you were younger, Bruce.

Now turn that frown upside down and live like you acted in The Dark Knight with the Lamborghini, and buying the restaurant, and the two hot girls.

And stop scowling. You’re so much more handsome when you smile, friend!

Terry Benedict – Ocean’s 11, 12, and 13

Terry Benedict is one of the few self-made men on this list, but that doesn’t free him from the sourpuss affliction that hits so many of the guys that are just born into money.

Terry struts around like everyone is trying to screw him, which is actually pretty prescient, because the entire Ocean’s franchise is predicated on people trying to screw Terry Benedict. Also, maybe he feels ridiculous and wallows in shame because he’s always dressed in insane Asian-inspired suits that make him look like a monk attending the White House Correspondents’ Dinner. In any event, he’s a Grumpy Gus, and I don’t just throw around the phrase “Grumpy Gus.” Why would I?

Sebastian Valmont – Cruel Intentions

He’s sex obsessed, but not in a funny Jason Biggs-in-American-Pie way, but rather a “there’s nothing that will ever fill the emptiness I have from being a privileged bastard” way. He’s about two steps away from being a total Patrick Bateman, but he manages to sort of, kind of, make good by the end of the film, even though he’s still pretty much a dick.

Smile, Sebastian. You’ve got a great car, a great townhouse, and well-tailored shirts and hunting outfits. If you’re ambling around Manhattan, try to run into Thomas Crown. He’s insanely rich as well, but seems to derive a little more pleasure from his good fortune than you do.

Money’s only a curse if you let it be.

I just made that up, but it could be right. Mo’ money, mo’ problems, my ass.

The Malfoys – Harry Potter

You’ve got SO much money, Malfoys. Why can’t you give up the whole “flirting with evil” thing and just buy an island and sponsor a Formula One team instead of teaming up with that whose name we shouldn’t be saying? You know, the V-word. Well, one of the v-words. The Malfoys are definitely what you would consider “old money,” but that’s no excuse for being evil, though it is pretty clear that the loner money has been in a family, the more likely it is that the character will be joyless and just grumpy.