#10 - Marcellus Wallace
Illegal activities: Murder, gambling, corruption
Marcellus Wallace is an elusive and mysterious man. He’s got an attractive young wife named Mia and several hit men in his employ. His motivations are equally enigmatic and he sends out his men to retrieve a suitcase, which has unknown, but valuable, contents inside. And if you happen to get the best of him one day, you won’t be enjoying it for long because he holds a grudge.
Boss’ orders: “I'ma get medieval on your ass.”
#9 – XXXX
Illegal activities: Drug dealing, racketeering
XXXX (the unnamed protagonist of Layer Cake, played by Daniel Craig) is planning on retiring from the criminal world after years of doing business on his terms. He played it as safe as a drug dealer can play it, but now that he’s on the verge of retirement, he has to find the daughter of a business associate and negotiate a deal for 1 million ecstasy pills. Unfortunately for XXXX, these last few days before retirement are going to be difficult, but luckily he’s a smooth operator who’s got a way with the ladies and knows his way around London’s underbelly.
Boss’ orders: “It is vital that we work to a few golden rules. Always work in a small team. Keep a very low profile. Only deal with people who come recommended. And it's like selling anything else: washing machines, handmade shoes, blow jobs. As long as you don't take the piss, people will always come back for more. And that is not to say we don't have that special kind of magic that makes two kilos into three. But never be too greedy.”
#8 - Frank White
King of New York
Illegal activities: Drug trafficking, murder, racketeering
Frank White is a modern-day Robin Hood who decides to wipe out the competition, against the wishes of the corrupt law enforcement who would like to bust him. White’s plan is to take the riches (money and drugs) that his competitors have accrued while White was in prison and turn that money into a hospital for the needy in South Bronx. White does very bad things in order to do great things.
Boss’ orders: “From now on, nothing goes down unless I'm involved. No blackjack, no dope deals, no nothing."
#7 - Nino Brown
New Jack City
Illegal activities: Drug trafficking, murder, corruption
While all the other drug dealers are selling cocaine, Nino has the revolutionary idea that the future of the drug market is in the rock form of cocaine: crack. This leads Nino to quickly rise in the ranks as one of the biggest drug lords the city has ever seen, and he’s soon making over $1 million a week from his operation. And the cops will do anything and break any rule to bring him down from his lofty perch.
Boss’ orders: “Money talks, and bullsh*t runs a marathon. So, see ya and I wouldn't want to be ya.”
#6 - Tony Montana
Illegal activities: Drug trafficking, murder, racketeering
Tony Montana is a Cuban immigrant who wants to make it in America once he washes ashore on Miami Beach. He finds that the quickest way to the top is to be in the cocaine business. It’s a meteoric rise and then a crushing fall into a mountain of his precious white powder.
Boss’ orders: “Say hello to my little friend!”
#5 - The Joker
The Dark Knight
Illegal activities: Murder, kidnapping, racketeering, mayhem
Coming seemingly from nowhere, the Joker is a madman hell-bent on the destruction of Gotham City and the unmasking of Batman. He has a permanent smile carved into his face, but his story for how it happens changes every time he tells it. He’s a psychopath that likes to see mayhem just for the joy of watching things burn and crumble, but he has a great time doing it.
Boss’ orders: “If you're good at something, never do it for free.”
#4 - Frank Costello
Illegal activities: Murder, drug dealing, racketeering
Vicious and methodical, Frank Costello is respected in his community by some and vilified by others. He does vicious things, but usually only to those who are duplicitous. He takes a young man under his wing and helps to keep him safe and happy, but he expects a large favor to be done on his behalf: to infiltrate the Boston Police Department and report back to him. Costello thinks long-term, but things have a way of catching up.
Boss’ orders: “When I was your age, they would say we can become cops or criminals. Today, what I'm saying to you is this: When you're facing a loaded gun, what's the difference?”
#3 - Michael Corleone
The Godfather: Part 1, 2 & 3
Illegal activities: Racketeering, gambling, money laundering, murder
Michael is the favorite and youngest son of Vito Corleone and after a stint in the army, he was supposed to go on and do great things with his life. But when his father is shot and the family falls to pieces, Michael is the only one with the smarts to keep it all together. Michael doesn’t so much take the position that his father once held so much as he was the only man for the job. Michael does his job much more methodically than his father and he’s got a vicious cold streak that runs deep within him.
Boss’ orders: “Keep your friends close and your enemies closer.”
#2 - Tony Soprano
Illegal activities: Multiple murders, racketeering, gambling, money-laundering
Tony (James Gandolfini) is the head of two Soprano families: the notorious New Jersey crime family and his own family with his wife and two kids. Tony is equally dedicated and equally frazzled by both families. When he spends too much time on one, the other suffers. It doesn’t help that Tony is prone to having affairs, as well as suffering from panic attacks that take him to therapy. In other words, Tony Soprano is just like us (if we were the head of a major crime syndicate).
Boss’ orders: “If you can quote the rules, then you can obey them.”
#1 - Vito Corleone
The Godfather: Part 1&2
Illegal activities: Racketeering, gambling, bootlegging, the murders of Don Ciccio and Don Fanucci
The head of the Corleone crime family, which is the most powerful in New York City, Vito Corleone makes his way up the ranks by being smart and dedicated. Vito’s No. 1 goal as a kid was to protect his family at all costs, and that loyalty stayed consistent as he got older and had a family of his own. His kids are the pride and joy of his life, especially young Michael, who he hopes will lead the legitimate life that he never got.
Boss’ orders: “I'm gonna make him an offer he won't refuse.”