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
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
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
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?”