Gangsters have always been a favorite movie topic. From The Public Enemy (1931), to The Godfather (1972), to The Departed (2006), Hollywood just can’t get enough of these morally troubling figures and their rise and fall. While some movie gangsters are fictional, there are just as many movie gangsters based on real people. One such case is Johnny Depp’s upcoming portrayal of Irish mobster Whitey Bulger in Black Mass. No one wants to get on the wrong side of a gangster, but especially not one like Bulger, who was often referred to as a sociopath during his well-publicized trial for 19 murders.
Some gangsters are more ruthless and terrifying than the rest. They are the ones who go out of their way to intimidate and frighten those around them. And they will stop at nothing to seek revenge against those that have wronged them. Here’s a look at Screen Rant’s 10 Most Ruthless Movie Gangsters.
Tony Montana in Scarface (1983)
The 1983 film Scarface, directed by Brian de Palma, tells the story of a Cuban refugee, Tony Montana (Al Pacino), who makes it big in Miami by becoming a drug kingpin. A remake of a 1932 Howard Hawks film of the same name, Scarface gained notoriety for its graphic use of violence and drug use. The entire movie has an over-the-top feel to it; in one notorious scene, a man has his body cut up with a chainsaw and thrown out of helicopter. There’s nothing subtle about the way Tony Montana handles business.
The entire movie could have easily devolved into pure camp had it not been for Al Pacino’s performance as Tony Montana. There’s no question it’s a divisive performance – the whole movie is a love it or hate it proposition – but for those who admire the film, Pacino’s brash performance was the key to the film’s success. Tony Montana came from nothing and literally fought and clawed his way to the top of an empire. He wasn’t a cool and collected businessman (that was Michael Corleone in The Godfather). Montana is instead fueled by cocaine, jealousy, and recklessness.
Tommy DeVito in Goodfellas (1990)
There’s a reason Joe Pesci won an Academy Award for his portrayal of Tommy DeVito in Martin Scorsese’s classic crime film Goodfellas. Pesci’s performance was stellar throughout the film, as a gangster that was a powder keg of violence just waiting to explode. DeVito wasn’t intimidating in his size or physical strength, but that didn’t stop him from being the most threatening man in the room.
Usually it’s good form to laugh at your superior’s jokes, but when fellow mobster Henry Hill (Ray Liotta) cackles during one of DeVito’s stories and calls him a ‘funny guy’, Pesci has his finest moment in the film. “I’m funny how? I mean funny like I’m a clown? I amuse you?” With these words Pesci takes a light and funny moment and turns it into a terrifying confrontation that quiets an entire table. Will DeVito start laughing back or pull out his gun and start shooting? You just don’t know, and that’s why it’s a classic moment.
Nino Brown in New Jack City (1991)
Wesley Snipes’ best performance can probably be found in Mario Van Peebles 1991 crime thriller New Jack City. Snipes plays drug lord Nino Brown, who takes advantage of the widespread use of crack-cocaine in New York City to make his fortune. Nino Brown is ruthless, but he is also charming, which makes for a deadly mix to those in his inner circle. Brown is willing to kill his close friends if it benefits his drug empire, and isn’t above using a child as a shield for himself in a gunfight.
Brown, like most gangster kingpins, is an egomaniac who can’t see beyond his own visions of power and fame. The Brown character has drawn many comparisons to the film Scarface, which several characters in New Jack City are shown watching on television during the film. While Brown claims again and again that what he does is “business and not personal,” his community takes his violent and destructive actions very personally. When Brown is brought to court for his crimes, he unsurprisingly blames everyone and everything except himself for the damage he has caused.
Mr. Blonde in Reservoir Dogs (1992)
Many people categorize Reservoir Dogs as a heist film, but if the definition of gangster is “a member of a gang of violent criminals,” then the characters of Reservoir Dogs seems to fit the bill. And among this impromptu gang of jewel thiefs, there is no one as violent, sadistic, and psychopathic as Mr. Blonde (Michael Madsen).
After cops show up at the heist and it turns into a bloodbath, several characters refer to Mr. Blonde’s unnecessary killing of innocents as the start of the trouble. If that isn’t bad enough, Mr. Blonde has taken a police officer hostage. After being left alone with the officer, Mr. Blonde tells him he doesn’t really care what he does or doesn’t know. He’s just going to torture him for his own amusement. And in a scene that will forever change your memories of the song “Stuck in the Middle With You,” Mr. Blonde does exactly that. Mixing torture with jokes and really bad dancing, all while remaining calm and cool, Mr. Blonde is as ruthless as they come.
Marsellus Wallace in Pulp Fiction (1994)
You know who isn’t a good man to cross? Marsellus Wallace. The 1994 Tarantino film Pulp Fiction interwove the storylines of dozens of characters in a singularly unique crime tale. John Travolta and Samuel L. Jackson’s characters (Vincent Vega and Jules Winnfield) had some of the most memorable scenes in the film as enforcers for their boss, gangster Marsellus Wallace. In one of these scenes, Vega and Winnfield describe how Wallace previously had a man thrown off a fourth story balcony after he gave Wallace’s wife a foot massage. In another scene, the duo show no mercy to a bunch of college kids who have stolen from Wallace. There is no good ending in Pulp Fiction when you cross Wallace.
Ironically, Wallace’s ruthlessness is most on display in Pulp Fiction in a scene where he is the victim. After chasing Butch Coolidge (Bruce Willis), a boxer who refused to throw a fight for Wallace, both Willis and Wallace end up as captives in the basement of a sadistic pawn shop owner. When Wallace escapes, his first move is to shoot the man that was just violated him. Wallace doesn’t acknowledge anyone or anything else in the room, except the man that is now his prey. Wallace tells the man “I’m ‘a get medieval on your ass,” and you know that whatever is about to happen is going to be horrifying.
Dutch Schultz in Hoodlum (1997)
It’s a special kind of gangster that can take several shots to the gut and then calmly sit down at a table as if he’s about to order a drink. In Hoodlum, Tim Roth plays real life gangster Dutch Schultz and the film follows the turf war between his former employer Lucky Luciano (Andy Garcia) and Ellsworth “Bumpy” Johnson (Laurence Fishburne), who controls illegal activities in Harlem.
Dutch’s tactics to expand Luciano’s numbers rackets into Harlem are so violent he is even off-putting to other criminals. Dutch, with his disturbingly joyful facial expression, kills without thought or mercy, and pulls a gun out in a crowded nightclub with no thoughts about anyone else’s safety. Dutch clearly enjoys the violence and brutality that come with his work in the mafia.
Don Logan in Sexy Beast (2000)
Don’t ask Don Logan to put out a cigarette on an airplane. Trust us. In Sexy Beast, Ben Kingsley brought criminal, and arguable sociopath, Don Logan to life in a film where Logan tries to recruit a bank robber for one last heist. There is nothing appealing about Logan’s character. He’s a lying, manipulative and violent man who won’t take no for an answer.
Logan can be loud, aggressive, and out of control, or chillingly calm and composed. His unpredictability is one of the things that makes him a terrifying character. One moment he’s threatening and verbally abusing the crew and passengers on an airplane, and the next he’s making up stories about being abused to avoid police detention (there are hints of Heath Ledger’s Joker in the way he can’t be trusted to tell you the truth about his own history). Logan is a dangerous wild card who finds success through intimidation and fear. It’s a mesmerizing and terrifying performance from Kingsley.
Arthur “Cody” Jarrett in White Heat (1949)
James Cagney became famous portraying a variety of gangsters in his film career. These performances are memorable to this day because of the unbridled bravado and sense of urgency that Cagney brought to these characters. While Cagney’s most famous gangster movie is The Public Enemy, the character he portrayed in White Heat was the most ruthless.
In White Heat, Cagney plays Arthur “Cody” Jarrett, a gangster driven mad by headaches and an unhealthy relationship with his mother (cue the Freudian analysis). Cody is a killer, but he’s also smart enough to confess to a lesser crime to get an alibi for a much more serious offense. Nevertheless, even with a reduced sentence, he quickly breaks out of jail and takes hostages along the way. In one particularly horrifying display of ruthlessness, Cody fires a machine gun right into the trunk of his car, where a hostage was desperately asking for some fresh air. You’re either with Cody, or you are his enemy.
White Heat and Cagney’s performance have survived the test of time, as there continue to be references to the film in movies and music to this day; Madonna even named a track after the film on her album True Blue, which she dedicated to James Cagney.
Connor Rooney in Road to Perdition (2002)
There are several gangsters on this list with mother issues. But Connor Rooney (Daniel Craig) only has a serious daddy issue in Road to Perdition. Rooney is the son of an Irish crime boss John Rooney (Paul Newman) who favors one of his employees, Michael Sullivan (Tom Hanks), over his own son. Rooney is truly a son only a father could love. He has a penchant for unnecessary violence, and he’s been embezzling money from his father’s business.
Rooney is also burning inside with rage over his father’s relationship with Sullivan. When Sullivan’s son witnesses a crime, Sullivan insists to Connor and John Rooney that his son will not speak about what he saw. Connor however sees his chance to inflict pain on the rival for his father’s love, and murders Sullivan’s wife and younger son. While he may be a ruthless, sociopathic animal, Connor Rooney is also a coward. He gets others to do his dirty work for him while he stays out of harm’s way, and he goes into hiding when Sullivan seeks his revenge.
Pinkie Brown in Brighton Rock (1947)
Pinkie is the ultimate gangster sociopath who manipulates and uses those around him for his own purposes. In the 1947 film adaptation of Graham Greene’s novel Brighton Rock, Richard Attenborough plays the charming teenage hoodlum, who is also a cold-blooded murderer. After the leader of Pinkie’s gang, known for using straight-edge razors to get their way, is murdered by a rival group, Pinkie assumes leadership and elevates his position in the crime world through a string of brutal murders and a manipulated romance with a young girl. She thinks Pinkie truly loves her, when he’s really using her to cover his tracks with the police.
Attenborough was just 23 years old when he appeared in Brighton Rock, and was heavily praised for his performance as the evil and twisted Pinkie. The film’s ending had to be watered down from Green’s ending in the novel, as it was considered too disturbing for audiences. Even with a softer ending, the film was banned in some areas of Australia for its shock value. Interestingly enough, not even the remake of Brighton Rock, made in 2010 with Sam Riley in the lead role, was as dark as the novel.
Which gangsters on this list are the most ruthless? Which ones did we leave off? Let us know what you think in the comments.