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.”
10. Keyser Söze
The Usual Suspects
Actor: Now that would spoil it, wouldn’t it?
Management style: Absolute ruthlessness. Deals with disloyal henchmen by killing them and all of their loved ones.
Best line (from Roger ‘Verbal’ Kint): “Keaton always said, ‘I don’t believe in God, but I’m afraid of him.’ Well I believe in God, and the only thing that scares me is Keyser Söze.”
9. Frank Costello
The Departed
Actor: Jack Nicholson
Management style: Make sure you’ve got your man on the inside.
Best line: “The only one that can do what I do is me. Lot of people had to die for me to be me. You wanna be me?”
8. Cody Jarrett
White Heat
Actor: James Cagney
Management style: Only trust your ma.
Best line: “I told you to keep away from that radio. If that battery is dead it’ll have company.”
7. Li’l Zé
City of God
Actor: Leandro Firmino / Douglas Silva
Management style: Kill ‘em all.
Best line: “Motherfucker! I’m the boss around here but he gets his picture in the paper! Have you found my photo in there?”
6. Al Swearengen
Deadwood
Actor: Ian McShane
Management style: Take advantage of the lawless frontier.
Best line: “Pain or damage don’t end the world. Or despair, or fucking beatings. The world ends when you’re dead. Until then, you got more punishment in store. Stand it like a man… and give some back.”
5. Avon Barksdale
The Wire
Actor: Wood Harris
Management style: Defer to lieutenant while in jail. Lament how everything’s gone “corporate.” Bring back the hood.
Best line: “I ain’t no suit-wearin’ businessman like you… you know I’m just a gangsta I suppose…”
4. Tony Montana
Scarface
Actor:Al Pacino
Management style: He’s not just the owner of the drug business. He’s a customer.
Best line: “You wanna waste my time? Okay. I call my lawyer. He’s the best lawyer in Miami. He’s such a good lawyer, that by tomorrow morning, you gonna be working in Alaska. So dress warm.”
3. Tony Soprano
The Sopranos
Actor: James Gandolfini
Management style: Do what you gotta do; seek counseling later.
Best line: “Let me tell ya something. Nowadays, everybody’s gotta go to shrinks, and counselors, and go on “Sally Jessy Raphael” and talk about their problems. What happened to Gary Cooper? The strong, silent type. That was an American. He wasn’t in touch with his feelings. He just did what he had to do. See, what they didn’t know was once they got Gary Cooper in touch with his feelings that they wouldn’t be able to shut him up! And then it’s dysfunction this, and dysfunction that, and dysfunction ma fangul!”
2. Michael Corleone
The Godfather series
Actor: Al Pacino
Management style: Be smarter—and colder—than everyone else.
Best line: “If anything in this life is certain, if history has taught us anything, it is that you can kill anyone.”
1. Don Vito Corleone
The Godfather
Actor: Marlon Brando
Management style: Keep it in the family, rule like a judge and steer clear of the drugs.
Best line: “A man who doesn’t spend time with his family can never be a real man.”