Take the Cannoli

Kiryu Kazuma grew up in an orphanage and viewed the crime boss who killed his parents as a father figure. Following in the footsteps of his mentor, Kiryu joined the Yakuza and became feared as a member of the Tojo Clan. His life was put on hold, however, when he took the fall for a murder committed by his best friend. After serving ten years in prison, Kiryu discovered that his friend had gone into business for himself and managed to steal ten billion yen from the clan. Kiryu soon found himself in the midst of Yakuza family wars and was named Fourth Chairman of the Tojo Clan after a bitter battle with his former friend. He gave up the position to pursue other interests, but he was clearly qualified for the role. His tenure was too short for him to be rated higher on this list, but it takes balls to walk away from a job that people would literally kill for.

Vito Scaletta’s family moved to America from Sicily to start a new life, but his parents were unable to escape poverty and both died young. After serving time in the military and prison, Vito gave up on the American dream and looked to the criminal underworld for opportunity. He’s not above hurting or killing people for money, and his life as an up-and-coming gangster is glamorized at first. He pays a price for his actions, however. Vito ends up running his own gang and seizes control of a few territories as an underboss, but you have to question if it was worth the effort. Numerous crime families want him dead, he’s wanted by the FBI, and he lost most of his friends because of his profession. Vito becomes increasingly jaded as the series progresses, and he begins to view the Mafia as a dead-end-job with more risk involved.

The head of the Ashura-kai, Tayama was little more than a common gangster before demons invaded Tokyo. Tayama saw the cataclysmic event as an opportunity, and he began negotiating with the demons after their arrival. The safety of the underground districts partly stems from his efforts, and the Ashura-kai legitimately strives for peace. Their methods are violent and twisted, however, and the group gains power through extortion and protection rackets. Those looking to join the Ashura-kai are required to provide three children, but the organization doesn’t partake in garden variety human trafficking. Instead, they harvest human brains to make food for the demons in order to secure contracts. Tayama has the moral backbone of a chocolate eclair, and even demons are horrified by him.

Whether you know her as the boss, the queen, or the CEO, Aria T’Loak is the de facto ruler the space station Omega. After arriving on the station, Aria worked as an exotic dancer at the Aferlife Club before killing the owner and taking control of the establishment. From there, she continued to form alliances with others until she had enough power to claim the Omega as her own. Aria negotiates from a position of power and uses centuries of life experience to read others. Since she surrounds herself with loyal followers and has the entire crime world in her pocket, Aria is able to rule with absolute authority. Nothing that happens on the station escapes her notice, and even mercenary groups are afraid to cross her. Despite her hard exterior, she has just one rule: “Don’t fuck with Aria.”

Thanks to the Pokémon anime, Team Rocket is arguably the most notorious criminal organization in gaming. The group steals rare Pokémon from around the world and sells them to the highest bidder. They also conduct cruel experimental research and have even killed Pokémon. They proudly exploit Pokémon for profit and have the belief that all Pokémon exist for their glory. Giovanni claims to be the strongest Pokémon trainer and threatens to bring a world of pain to those who oppose him, but he repeatedly loses battles to children. He is forced to regroup on multiple occasions, but he works hard to restore Team Rocket to its former glory after each defeat. Pokémon are important tools for keeping Giovanni’s criminal enterprise going, so it is unlikely that he will ever stop exploiting them. Team Rocket’s blasting off again!

Johnny Gat is technically the second-in-command of the 3rd Street Saints, but his role is more akin to co-leader than a lieutenant. The Boss is a stoic and resourceful mastermind, but Johnny is a lot more interesting since he has the freedom to do whatever he wants. Johnny is obsessed with guns and violence and he would sooner blow things up than sneak around in the shadows. With 387 counts of murder to his name, Johnny is described as the most dangerous person on Earth. Whether he’s using an assault rifle to hold off the entire police force or killing aliens with only his fists and a knife, Johnny is a badass of the highest magnitude. The Saints eventually become international celebrities, but even after the Boss is elected President of the United States, he never stops looking up to Johnny.

Geese Howard is the local crime boss of South Town and the main antagonist in the Fatal Fury franchise. He’s responsible for illegal acts ranging from kidnapping to murder, and he’s so arrogant that he hosts fighting tournaments to confront those seeking vengeance against him. His ego is somewhat inflated, but it’s hard to deny his abilities. Not only is Geese a skilled fighter, but he’s almost impossible to kill. He’s presumed dead after falling from a high-rise building, but he somehow survives. He later gets knocked off the tower again, only to return as a ghost! A younger version of Geese shows up in Art of Fighting 2 as a corrupt police commissioner, and he’s revealed to be the true mastermind behind all the shady events that unfold in that series as well. I guess his crimes simply couldn’t be contained in a single franchise.

Heihachi Mishima is the on-again/off-again head of a multinational conglomerate called the Mishima Zaibatsu. While ostensibly a financial group, the Zaibatsu functions more like a criminal organization. At one point, Heihachi creates a private corporate army called the Tekken Force and dispatches them around the globe to end small conflicts in foreign countries. The army helps Heihachi gain favor with the public, but his true intentions are for world conquest. Heihachi is one of the strongest Tekken characters, but he’s also one of the most unbalanced. Whether he’s throwing his son off a cliff to test his strength, trying to combine his own DNA with an ogre’s, or simply showing up as a competitor in Anna Kournikova’s Smash Court Tennis, Heihachi comes across as an aging grandfather who is beginning to lose his sanity.

M. Bison is known as Vega in Japan, but some gamers refer to him simply as Dictator. It’s a fitting title, as Bison aims to control the world through his covert crime syndicate, Shadaloo. The specific goals of the organization are ambiguous, but Bison wields an inherently evil energy known as “Psycho Power” and uses a machine to channel psychic energies. When the power exceeds the limits of his body, Bison’s scientists devise a way to transfer his essence into a new host. This allows him to cheat death on multiple occasions. Bison rules with an iron fist, but he’s also familiar with the art of persuasion. He uses the promise of wealth to enlist lieutenants and brainwashes teenage girls to act as bodyguards. He makes enemies of Interpol, the US Air Force, and a myriad of martial artists, so I guess he needs all the backup he can get.

Tommy Vercetti worked his way up through the ranks of the Forelli crime family, but a hit was ordered against him when he started to gain power. After killing all 11 men who were sent to ambush him, Tommy was taken into police custody. He refused to reveal any info about the Forellis, however, so the family pulled some strings to spare him the death penalty. After spending 15 years in the big house, Tommy was sent to Vice City to expand the drug trade in the south. Tommy was involved in smuggling and protection rackets, and he began buying businesses around the city to expand his influence. After instigating conflicts between rival gangs, Tommy found himself in control of Vice City’s criminal underworld. He has anger issues and often trusts people he shouldn’t, but his sense of loyalty is admirable and his work ethic is unrivaled.