29. Andrew Cunanan
He murdered Versace, so you know he has no taste. He’s probably all about being the iron and makes a big deal about calling dibs on it. Everyone knows that’s the worst one!
28. Fritz Haarmann, The Butcher Of Hanover
Also known as The Vampire of Hanover, also known as The Wolfman, also known as “Hey buddy, pick a lane!” He would probably spend the whole game trying to give himself cool new nicknames. That’s not how it works!
27. Patrick Kearney, The Freeway Killer
The Freeway Killer is the Captain Marvel of serial killers, not because he’s awesome at it but because there are three other killers named The Freeway Killer. With so many contenders to the throne, he’s gonna try way too hard to be on brand the whole game. We get it dude, you want the race car, chill.
26. Richard Speck
He was originally sentenced to death for killing nursing students in Chicago, but did some hard finagling to get his sentence reduced to a scant 1,200 years. Something tells us he’s only playing to get that “Get Out Of Jail Free” card and we don’t wanna be around when he finds out it doesn’t work that way.
25. Israel Keyes
There are two kinds of serial killers: ones that make people say “Really? He seemed so nice!” and ones that make people say “Yeah that totally tracks.” If you’re going to play the Parker Brothers classic with a murderer you want the former, and Israel is strongly the latter.
24. Irina Gaidamachuk, The Satan In A Skirt
She’s a raging alcoholic, and there’s nothing as annoying as playing a board game with a drunk. They never remember their turn, they accuse you of cheating when you’re not, they murder you with a hammer and pick your pockets for booze money, it’s just a bad time.
23. Charles Cullen
Is there anything creepier than a nurse murderer? Charles killed over 50 patients in his career through “accidental” overdose and he’s a stone-cold bummer to boot. Between his sob stories and the repetitive tedium of Monopoly it’s only a matter of time before you nod off, and as soon as you do, it’s “medicine time.”
22. Karl Denke
Super annoying Monopoly player. He’s German so he doesn’t understand English, he was born in the 1800s so he doesn’t know the rules and he eats people. Annoying.
21. Myra Hindley And Ian Brady, The Moors Murderers
Ever been invited to a couple’s board game night only to realize the hosts are swingers feeling you guys out? Picture that level of annoyance, but with child murder.