We all know that the classic Parker Brothers board game Monopoly can bring out the worst in people. Friendships, relationships, and even familial bonds have ended on Park Place. With its potential to turn good people bad, imagine what effect it could have on the most despicable people to ever live.
We’ve compiled a list of some of the most deranged serial killers of all time and ranked them by how absolutely insufferable they would be playing Monopoly.
And it should go without saying, but this list mentions the violent crimes of all these killers, if you are sensitive to that material then we have a Seinfeld list that might be more up your alley.
50. Charles Manson
Technically Charlie is an honorary serial killer since we have no proof he actually killed anyone, but come on, he’s Manson, he’s in the conversation. He ranks last because frankly of all the deplorable people on this list, he’s your best shot at having a good time. He wouldn’t follow the rules of Monopoly or any rules for that matter, but he’s entertaining, he has acid and you might even get a Brian Wilson story or two.
49. John Wayne Gacy, The Killer Clown
He’s one of the worst of the worst people to ever live for sure, but he’s also an entertainer. He could probably be halfway pleasant through an evening of Monopoly if he were so inclined, just throw him some KFC and he should behave,
48. Rodney Alcala, The Dating Game Killer
Creepy, opinionated, and responsible for the deaths of anywhere from 10-130 people, Rodney’s a bad guy, but we have actually seen him play a game before, and although he was so weird off camera the contestant refused to go through with the date, he was charming enough to win.
47. Elizabeth Bathory
There’s just enough spooky horse girl in us to think meeting Elizabeth Bathory would be pretty cool.
46. Edmund Kemper, The Co-Ed Killer
Kemper’s crimes are insanely gruesome, culminating in the murder, decapitation, and corpse humiliation of his own mother, but at least he’s honest. He called the police to confess his crimes, and when they didn’t believe him he called them back to say “No, seriously, come arrest me.” He would probably make the best banker out of anyone on the list.
45. Jack The Ripper
We have no idea who Jack The Ripper was so honestly there’s no telling how annoying he would be at Monopoly, but you could probably write a cool song about it.
44. David Berkowitz, The Son Of Sam
Cons: After a schizophrenic episode he murdered a bunch of people at the behest of his dog, whom he believed to be the avatar of an ancient god.
Pros: He has a dog!
43. Aileen Wuornos
There are so few female American serial killers that it feels messed up to call the most prolific one “annoying.”
42. Jeffrey Dahmer, The Milwaukee Cannibal
Between ‘90s nostalgia and the fact that he’s a total hunk, we wouldn’t say no to a game of Monopoly with Dahmer.
41. Paul John Knowles, The Casanova Killer
Another handsome charmer, as long as you don’t follow him passed GO to a second location you should be okay playing Monopoly with The Casanova Killer. Keep in mind he did go out wrestling a cop for his gun, so you might wanna just let him win.
40. Jack Unterweger
Okay, we’re just gonna say it, this guy is interesting! Born in Australia he committed murders in four different countries in the ‘60s and ‘70s. He got busted for one in Austria in ‘74 and went to prison, where he started a writing career. The Austrian literary elite loved his writing so much that they petitioned to have him released, and it worked! He went on to become a playwright for a while before getting bored and going back to murdering. Anyway, he must have a million stories, and game night seems like a perfect chance to hear some.
39. Carl Panzram
If you’ve read any of his writing, you know that a board game night with Carl Panzram wouldn’t be all that different from a board game night with any given grindcore frontman. That still sounds annoying, but not without a certain kitsch appeal.
38. Beverley Allitt
She killed a bunch of babies as a hospital nurse, so if she pulls that “Pay Hospital Bill” card with the Monopoly guy holding twin newborns shit could hit the fan fast.
37. Albert Desalvo, The Boston Strangler
Forget the fact that he killed 13 women in 2 years, the fact that he’s from Boston is all you need to know to be sure Albert Desalvo would be annoying to play Monopoly with or even be around.
36. Moses Sithole, The ABC Killer
He committed a series of brutal rapes and murders while managing a shell organization dedicated to fighting child abuse. Anyone capable of that level of cognitive dissonance is for sure going to try cheating at a child’s board game.
35. Harold Shipman, Dr. Death
It can be highly irritating to play a kid’s game with an educated professional. They often can’t accept the fact that their perceived intellectual superiority doesn’t equate to winning, and can lash out. They aren’t all like that of course, but this one killed 250 people, so he’s probably like that.
34. Kenneth Bianchi, The Hillside Strangler
A failed cop who targeted New York sex workers in the ‘50s and is still alive. Can’t wait to hear his politics on game night.
33. Wayne Williams
An aspiring music producer and alleged child mass murderer. We could tolerate a game night with one or the other but not both.
32. Ed Gein, The Butcher Of Plainfield
He would have zero interest in the game and would try to segue the whole evening into a crafts night. He won’t be dissuaded when you tell him you don’t have any craft materials on hand either… you ARE the craft materials!
31. Samuel Little
Little’s got the most confirmed kills out of any serial killer in U.S. history, so you know he’s a big competition freak.
30. Ottis Toole
Ottis may or may not be a serial killer. He was the accomplice of Henry Lee Lucas and corroborated a lot of his confessions, many of which were proven to be lies. It’s never fun playing a board game with a liar, but he’s a good friend, and that has to count for something.