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Top Ten Fictional Gangsters in Movie History Known for Their Ruthlessness

Gangsters and gangster movies have always been well-received in America and worldwide. People love romanticizing outlaws, thumbing their noses in the face of society’s rules. Gangsters rob and kill their way through life instead of getting regular jobs like the rest of us working shlubs.

Gangster movies allow these violent and sadistic characters to take center stage and are often the protagonists. These films flip the typical storytelling template, making criminals into antiheroes. Despite this romanticism, gangsters are callous, sometimes enjoying their acts of evil. Robbing and killing takes a certain ruthlessness that most people just don’t have. Movie buffs worldwide have favorites, from Vito Corleone to Vincent Vega and everyone in between.

With that in mind, we have compiled a list of the ten most ruthless gangsters in movie history.

10 Vincenzo Coccotti: True Romance

Vincenzo Coccotti is consigliere for Detroit-based mob boss “Blue” Lou Boyle, and he hasn’t personally killed anyone since 1984. That is until Clarence Worley and his new wife, Alabama, steal Boyle’s cocaine from Alabama’s ex-pimp, Drexl. Christopher Walken plays Coccotti with genuine menace, towering over a tied-up Dennis Hopper, playing Clarence’s dad as he brutally interrogates him for his son’s whereabouts.

Clarence’s dad turns the tables on the mobster by insulting his Sicilian heritage until he snaps and breaks a years-long no-kill streak (since 1984). It is one of the most memorable scenes Quentin Tarantino has ever written, and Walken really sells the gangster’s unbridled fury when he’s embarrassed.[1]

9 Tony Montana: Scarface

One of the most quotable movies of all time, Scarface chronicles the life and times of Tony Montana. Early in the film, Montana is traumatized by chainsaw-wielding gangsters. “Instead of taking that experience as a warning sign and turning his back on crime, he decides to match their brutality.” As Tony climbs his way up through the Miami underground, he becomes more and more brutal.

Montana eventually turns on the people closest to him, and worse, he breaks the first rule of drug trafficking; he starts getting high on his own supply. By the film’s end, he’s unleashing an arsenal of firearms (one of which he refers to as his “Little Friend”) on an army of assassins sent to take down his empire. It is one of the most iconic and epic finales of any gangster movie.[2]

8 Mr. Blonde: Reservoir Dogs

Reservoir Dogs is a cult classic and Quentin Tarantino’s directorial debut. While the film never got any traction at the box office, it is now well-known and frequently viewed as a classic gangster flick. The plot is of a bank heist gone wrong. The film flips back and forth from past and current events. While the bank heist itself isn’t shown on screen from what the crew says, Mr. Blonde started arbitrarily executing civilians. After blowing the theft, Blonde stops for a burger and a coke and kidnaps a cop on his way to the rendevous.

After displaying an utter lack of respect for life, this heartless gangster cuts off the cop’s ear while listening to ’70s soft rock and dancing around in a carefree bloodbath. While Mr. Blonde is not the mastermind behind the crime, he is the archetypal gangster character incapable of professionalism. He is a terrifying character, as neither friend nor foe is safe from his violent tendencies.[3]

7 Carlito Brigante: Carlito’s Way

Carlito Brigante is not your typical gangster, at least not anymore. At the start of this film, the title character is released from prison and sets out to make a legitimate life for himself. What gets Brigante on this list is that he was such a ruthlessly violent criminal before he was locked up that his reputation precedes him on the streets years later.

Superbly played by Al Pacino, Carlito whispers, “The streets are watching,” referring to his reputation and the many obstacles standing between him and a normal life. However, he tries to leave his life of crime behind and retire in the Bahamas with his girlfriend, Gail. Circumstances conspire against him when Carlito unknowingly accompanies his young cousin to a drug trade, which quickly goes awry.

Carlito is forced to shoot his way out and kill the dealers to escape. While Carlito would prefer a life less violent, his professionalism and survival instincts make him one of the most ruthless gangsters ever to grace the silver screen.[4]

6 Keyser Söze: The Usual Suspects

According to the main protagonist, petty con artist Roger “Verbal” Kint (Kevin Spacey), Söze is a crime lord whose ruthlessness and influence have acquired a legendary, even mythical, status among police and criminals alike. Further events in the story make these accounts unreliable; in a twist ending, a police sketch identifies Kint and Söze as the same. The character was inspired by real-life murderer John List and the spy thriller No Way Out, which featured a shadowy KGB mole that may or may not have existed in real life.

Söze is the only figure on this list who is both unmercifully murderous and Machiavellian. Maybe he is a Hungarian drug czar who killed his own family to make a point, or perhaps that’s just another myth from this gangland master of personal branding. Ultimately, Keyser Söze’s best weapons are fear and deception. His misdirection alone makes him one of the most iconic gangsters ever.[5]

5 Tommy DeVito: Goodfellas

Based on real-life mob hitman Thomas DeSimone (aka Two-Gun Tommy), Tommy DeVito is a cruel associate of the Lucchese crime family and arguably the most feared member of the crew. As the years go by, Tommy moves from fencing contraband to hijacking trucks alongside Jimmy Conway, who is just one step below their crime boss, Paulie Cicero. Tommy’s fearsome temper and aptitude for violence make him a valuable team member.

Unfortunately, by 1963, Tommy’s sociopathic behavior has grown almost uncontrollable, making even the simplest of conversations a minefield for the others: He apparently doesn’t like being called funny. Tommy had a penchant for harassing civilians and threatening his coworkers. In the end, the mob has to put him down like a dog, and he sees it coming at the last second, making the scene brutal and devastating. Tommy’s ruthlessness came from a natural aptitude for violence and years of unchecked aggression.[6]

4 Michael Corleone: The Godfather Trilogy

The story of Michael Corleone is the quintessential gangster story. During the first film, Michael is the only one of the Godfather’s sons not vetted to follow in the family business. He attended an Ivy League school before going off to fight in WWII. Upon his return, however, the family enters a mob war, and his father, Vito (The Godfather), is severely wounded. The attack on his family awakens a darkness in Michael that starts with the gangland execution of a rival, Maffia Cappo, and a NYC police chief and goes on to claim countless victims.

Michael assumes his recently departed father’s role as Godfather at the first film’s conclusion. What sets Michael’s ruthlessness apart is his decision to have his own brother whacked at the second film’s end. While the young Godfather doesn’t take killing his brother, Fredo, lightly, he does feel it was the right “business decision” to make. By the trilogy’s end, Michael is alone. Everyone he has ever loved has either been killed in mob-related violence or left him.[7]

3 Professor Moriarty: Sherlock Holmes

Sir Arthur Conan Doyle’s legendary characters, Sherlock Holmes and Professor Moriarty, have endured for over a century. They have appeared in books, comics, TV series, and movies. In every incarnation, Holmes and Moriarty are each other’s equals in every conceivable way. They both represent the height of human intelligence, wit, and endurance. While Holmes uses his gifts to solve and prevent crimes, Moriarty is a crime lord.

Nothing happens in Moriarty’s city illegally without him (sometimes her) knowing about it. “He is the Napoleon of crime, Watson. He is the organizer of half that is evil and nearly all undetected in this great city. Moriarty is the hub through which most criminal enterprises of significance must pass what we call the ‘mastermind,’ Holmes explains to his trusted companion.”[8]

2 The Joker (Jack Napier): Batman (1989)

Since his first appearance in Batman #1 in 1940, countless incarnations of The Joker have occurred. Some of the TV and movie versions of this Clown Prince of Crime have been given subtitles by the fans. For example, Heath Ledger’s Joker is known as the anarchist, and Jack Nicholson’s is known as the gangster. In Tim Burton’s 1989 Batman, The Joker is given a definitive origin story, unlike his comic book counterpart.

He starts the movie as Jack Napier, a mob lieutenant. After a bath in a vat of toxic chemicals, courtesy of Batman, Napier, who already had violent tendencies, becomes The Joker. As the green-haired archnemesis of the Caped Crusader, no act of violence is too vicious. From lacing essential products with a lethal poison to shooting his right-hand man in the face, few characters, fictional or not, have been more ruthless. Jack Nicholson expertly portrays a mob boss gone mad and does this legendary character justice.[9]

1 Bodhi: Point Break

While it may be surprising, the bank-robbing surfer Bodhi is the most ruthless movie gangster of all time. Despite the stoner philosophy, Bodhi is just as much a gangster as any other famous bank robber, such as Bonnie and Clyde, and his modus operandi is the same. He and his gang of long-haired heshers might think they’re just stealing to finance some zen pursuit of endless summer, but that’s all self-deception.

In reality, he’s got more in common with Henry Hill from Goodfellas, who says of the working class, “They had no balls. If we wanted something, we just took it.” Bodhi is a great gangster, not because he’s different but because he’s just like the rest, with a “radical” new arsenal of excuses. What makes Bodhi a step more ruthless than the rest is his hypocrisy. He claims loyalty and solidarity to his crew, but there’s no one he wouldn’t turn on to save his own skin.[10]

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