Two episodes in, and Boardwalk Empire’s Nucky Johnson (Steve Buscemi) seems destined to become one of the all-time great fictional crime bosses. Of course, looking at the “best” fictional crime bosses really means looking at the meanest. Sure, they were good at what they did, but they weren’t “good” in any other sense of the word. These 20 men were utterly ruthless, but their ruthlessness accounted for much of the dramatic tension in some amazing movies, TV shows and comic books.
20. ‘Hatchet’ Harry Lonsdale
Lock, Stock & Two Smoking Barrels
Actor: P.H. Moriarty
Management style: Make lots of money so you can keep gambling.
Best line: “I don’t want to know who you use, as long as they’re not complete muppets.”
19. Wilton Fisk (Kingpin)
Marvel Comics (Spider-Man and Daredevil)
Actor: Roscoe Lee Browne, among others
Management style: Compensate for the lack of superpowers by learning and destroying the secret identity of his rival, Daredevil.
Best line: “I was raised in the Bronx, Wesley. This is something you wouldn’t understand.”
18. Leo O’Bannon
Miller’s Crossing
Actor: Albert Finney
Management style: A sense of fairness and mercy that don’t bode well for a fictional crime boss.
Best line: “Johnny, you’re exactly as big as I let you be, and no bigger, and don’t forget it, ever.”
17. “Proposition” Joe
The Wire
Actor: Robert F. Chew
Management style: Cautious and opportunistic. That’s why the Eastside runs smoothly.
Best line: “Omar to one side holding a spade, and maybe Marlo to the other with a shovel, and just at this moment, I manage to crawl out my own damn grave. No way do I crawl back in.”
16. Marcellus Wallace
Pulp Fiction
Actor: Ving Rhames
Management style: Get the two coolest henchmen (played by Samuel L. Jackson and John Travolta) to do your dirty work.
Best line: “Yeah, we cool. Two things. Don’t tell nobody about this. This shit is between me, you, and Mr. Soon-To-Be-Living-The-Rest-of-His-Short-Ass-Life-In-Agonizing-Pain Rapist here. It ain’t nobody else’s business. Two: you leave town tonight, right now. And when you’re gone, you stay gone, or you be gone. You lost all your L.A. privileges. Deal?”
15. “Boss” Rupert Thorne
DC Comics (Batman)
Actor: John Vernon, among others
Management style: Whatever it takes to keep Gotham open for crime.
Best line: “All men have something to hide. The brighter the picture, the darker the negative.”
14. Brick Top Polford
Snatch
Actor: Alan Ford
Management style: Threaten to feed the bodies of disobedient underlings to the pigs and torch buildings with their family members.
Best line: “Do you know what “nemesis” means? A righteous infliction of retribution manifested by an appropriate agent. Personified in this case by an ‘orrible cunt… me.”
13. Nino Brown
New Jack City
Actor: Wesley Snipes
Management style: Megalomania and intimidation with a dash of paranoia.
Best line: “Sit your five-dollar ass down before I make change.”
12. Jabba The Hutt
Star Wars series
Actor: Larry Ward
Management style: Business first, but that doesn’t keep him from enjoying the fruits of his labor—or enjoying punishment for those who fail.
Best line: “Han, Han, I can’t make exceptions. What if everyone who smuggled for me dropped their cargo at the first sign of an Imperial Starship. It’s not good business.”
11. The Joker
The Dark Knight
Actor: Heath Ledger
Management style: A pencil-pusher only in the literal sense of the word, he’s not in it for the money and doesn’t have the slightest regard for his underlings.
Best line: “Don’t talk like one of them. You’re not! Even if you’d like to be. To them, you’re just a freak, like me! They need you right now, but when they don’t, they’ll cast you out, like a leper! You see, their morals, their code, it’s a bad joke. Dropped at the first sign of trouble. They’re only as good as the world allows them to be. I’ll show you. When the chips are down, these… these civilized people, they’ll eat each other. See, I’m not a monster. I’m just ahead of the curve.”