Summary
- Gangsters are not just glamorous figures on screen; they are terrifying individuals capable of ruthless violence and psychopathy.
- Hollywood has created iconic gangster characters, played by talented actors, that have left lasting impressions on cinema history.
- Beyond the glitz and charisma, gangsters like Tom Powers, Sonny Corleone, and Nicky Santoro are ruthless killers with no remorse.
America has always had a fascination with gangsters, thanks to real-life mobsters like Al Capone and Lucky Luciano. Their headline-grabbing crimes and wealthy lifestyles made them sensations in the early 20th century. In response, Hollywood churned out gangster movie after gangster movie, giving the American people what they wanted: crime, glamour, and bloodshed on the big screen. Since then, we’ve watched some of Hollywood’s greatest actors shoot their way into cinema history, playing iconic and memorable gangsters.
But it’s time to look beyond the glitz and charisma and face the truth: gangsters are terrifying people. We’re talking about ruthless killers who often get away with murder. Many gangsters can be defined as legitimate psychopaths, who revel in bloodshed and go from 0 to 100 in the blink of an eye. Some of these characters are entirely fictional. Others are based on real people, men who have actually done what we’ve seen them do on screen, which only makes them that much more frightening. Sure, you might find yourself rooting for these gangsters from time to time. But at the end of the day, they’d murder you on the spot without even feeling an ounce of remorse. Without further ado, here are nine of cinema’s most terrifying gangsters who you would never, ever want to upset.
9 Tom Powers – The Public Enemy (1931)
James Cagney starred in several gangster classics during the 1930s, but The Public Enemy is regarded as his crowning achievement. Set during the Prohibition era, The Public Enemy captures the rise of Tom Powers (Cagney) in America’s criminal underworld, as well as his inevitable downfall. As simple as it sounds, The Public Enemy is a milestone in the genre that’s inspired every gangster movie since its release.
A Dangerous Man, Especially with Grapefruits
Long before there was James Caan’s Sonny Corleone or Joe Pesci’s Tommy DeVito, there was Cagney’s Tom Powers. With his tough guy attitude and arrogant smirk, James Cagney perfectly captures the gangster archetype.
Powers is a loose cannon with an unhealthy need to be the toughest guy in the room. He isn’t afraid to use force to get his way, whether it’s with fists or with bullets. Powers will snap on anybody who crosses him, including his own girlfriend. This is most evident in The Public Enemy’s most famous scene, when Powers aggressively smashes a grapefruit into his girlfriend’s (Mae Clark) face. It’s a jarring moment, even for today’s audiences. Stream The Public Enemy on Tubi.
8 Sonny Corleone – The Godfather (1972)
The Godfather is considered to be one of the greatest films ever made. It’s arguably the most significant milestone of the gangster genre, a masterpiece that’s inspired every film that’s followed it — and we’re not just talking about gangster movies. The Godfather is the first entry in a three-part saga that follows the powerful Corleone crime family. This particular installment focuses on its aging patriarch, Vito (played to perfection by Marlon Brando), and the family who steps up to help him after an unexpected shooting places him in the hospital.
The Family Hothead
There are many different personalities and temperaments in the Corleone family. Sonny Corleone (James Caan), Vito’s eldest son, is known as the family hothead. He has anger issues that dominate his judgment and self-control, which also worries the people around him. Most of Sonny’s scenes show him getting restrained at one point or another. We catch a glimpse of Sonny’s rage very early in the movie, when he goes ballistic on a cop for photographing license plates during his little sister’s wedding.
His most famous outburst, though, occurs after his brother-in-law physically abuses his little sister, Connie (Talia Shire). Blinded by rage, Sonny beats his brother-in-law bloody in the middle of a crowded street. Sonny becomes the Don after his father is gunned down. But his uncontrollable rage prevents him from being a competent leader — and eventually leads to his undoing. Stream The Godfather on Paramount+.
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7 Mr. Blonde – Reservoir Dogs (1992)
Reservoir Dogs is the movie that put acclaimed filmmaker Quentin Tarantino on the map. It follows several strangers from the criminal underworld who are brought together by a mutual connection to pull off a diamond heist. There’s just one problem: one of them is an undercover cop. Told in a non-linear fashion, we watch as the planned heist goes terribly awry, with clues as to who the undercover cop is slowly unraveling throughout.
“Stuck in the Middle with You”
Victor Vega, better known by his alias Mr. Blonde (Michael Madsen), is one of the criminals who was recruited into the diamond heist. He’s an enforcer for Los Angeles crime boss Joe Cabot (Lawrence Tierney) and his son Eddie ‘Nice Guy’ Cabot (Chris Penn). But don’t let Mr. Blonde’s calm demeanor fool you. Beneath that cool exterior lies a heartless and violent psychopath, and that’s the scariest part about him. He’ll casually cut off your ear while dancing to music — which he actually does in the film’s most iconic scene.
Here, Mr. Blonde confesses an enjoyment of torture and proceeds to demonstrate this on a tied-up cop, slicing off his ear with a straight razor and then dousing him in gasoline to light him on fire, all while the upbeat tune “Stuck in the Middle with You” by Stealers Wheel plays in the background. It’s a harrowing scene, and had Mr. Blonde not meet his demise shortly after, the end result would’ve been incredibly grisly. Stream Reservoir Dogs on The Criterion Channel.
6 Michael Corleone – The Godfather Parts I and II
Unlike his brother Sonny, Michael Corleone (Al Pacino) takes after their father, Vito. He’s a smarter, more competent, and strategic leader. But Michael is also a lot more ruthless, and more frightening, than his father ever was. Michael wields an enormous amount of power and influence, which reaches all the way up to the American government. He can get away with whatever crime he wants, as he’s proven time and time again during The Godfather saga.
Nobody Is Safe, Not Even Family
In the first movie, Michael keeps his distance from his family’s criminal empire. But when his father is unexpectedly gunned down, Michael quickly volunteers to murder the assailant, transitioning seamlessly into a cold-blooded murderer. Later, in the film’s most iconic sequence, Michael uses his godchild’s baptism as an alibi to commit a string of murders — the last of which being the father of the child he just baptized.
You think that’s cold and heartless? The Godfather Part II kicks it up a notch. After nearly being gunned down himself, Michael becomes convinced that someone in his inner circle helped arrange his assassination. In one of cinema’s most iconic betrayals, the traitor is revealed to be his own brother, Fredo (John Cazale). Michael then has his own brother killed after feigning forgiveness. Nobody is safe, not even family, when it comes to Michael Corleone. Stream The Godfather Part II on Paramount+.
5 Nicky Santoro – Casino (1995)
Based on the true-crime book of the same name, Casino follows gambling expert Sam “Ace” Rothstein (Robert De Niro) to Las Vegas, where he finds himself running the Tangiers Casino for the Chicago Mafia alongside his best friend and mob enforcer Nicky Santoro (Joe Pesci). The casino’s success brings Ace and his crew wealth and power, on top of luxuries beyond their wildest dreams. But their illegal operations eventually come tumbling down like a house of cards, sending their lives spinning out of control faster than a roulette wheel.
Pesci’s Most Terrifying Performance
Nicky Santoro is based on real-life gangster Anthony Spilotro. In Casino, Santoro is a ticking time bomb of rage that can explode at any second. He intimidates basically everyone that he has a conversation with, including the people he loves most. Intoxicated with power (among other substances), Nicky turns on everyone who was once close to him, from his bosses back in Chicago to his best friend Ace, abandoning the Mafia code (as well as any moral code) that he swore to live by.
When Ace meets Nicky out in the desert, he’s afraid that Nicky might actually kill him and bury his corpse in the sand. We can’t blame him; nothing is off limits when it comes to Nicky, including torture. But in the end, Nicky’s evil acts come back to haunt him, giving him a death that’s as violent as his life. Buy or Rent Casino on Prime Video.
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4 Tony Montana – Scarface (1980)
Scarface is a remake of the 1932 gangster film of the same name, which was originally directed by Howard Hawks. Writer Oliver Stone and director Brian De Palma give it a fresh spin by focusing on Cuban gangster Tony Montana (Al Pacino) and his drug-fueled rise to power in 1980s Miami, complete with over-the-top violence and more iconic ’80s songs than you can count.
An Anti-Hero with a Short Fuse
Al Pacino delivers an unforgettable performance as Tony Montana, the movie’s short-tempered and violent anti-hero. Tony isn’t afraid of anyone, but almost everyone is afraid of him. He’ll do whatever it takes for money and power, even if it means killing everyone in his path (which he pretty much does). But even after obtaining success, Tony remains angry and hateful throughout the film. He kills his best friend and business partner for sleeping with his sister. And then guess what? He goes ahead and kills his sister, too.
Tony’s rage constantly clouds his judgment, making him dangerous and unpredictable. The guy is also an unstoppable force; even an army of assassins has trouble bringing him down. Even after taking half a dozen bullets, he’s still belting out iconic quotes until his ungraceful demise. In the end, Tony goes out angrily screaming at the world, an appropriate ending for a man who led a rage-fueled life. Stream Scarface on Hulu.
3 William “Bill the Butcher” Cutting – Gangs of New York (2002)
Set at the turn of America’s Civil War, Gangs of New York is an epic period piece that’s regarded as one of Martin Scorsese’s best movies. It pits two rival gang leaders against each other: Amsterdam Vallon (Leonnardo DiCaprio), who seeks revenge for his murdered father, and William “Bill the Butcher” Cutting (Daniel Day-Lewis).
The Most Dangerous Man in America
Daniel Day-Lewis delivers a transformative performance as Bill the Butcher. He’s a larger-than-life character whose shadow looms over New York City. Bill lives his life through fear and violence: he revels in violence while weaponizing fear, unfazed by the bloodshed that follows. At one point, he stabs a man in the hand during a card game and then carries on with the game like it’s nothing.
Bill strikes fear in the hearts of everyone around him; very few people dare to oppose him. His charisma draws everyone toward him, from the audience watching his scenes to his greatest enemies. Even Amsterdam develops an affection for Bill, despite the fact that Cutting murdered his father earlier in the film. Being a skilled fighter, Bill is also adept with knives and blades (they don’t call him Bill the Butcher for nothing). He knows every spot that can instantly kill a man on the human body, making him an efficient killer and a considerable threat to contend with. Stream Gangs of New York on Max.
2 Tommy DeVito – Goodfellas (1990)
Featuring an all-star cast and directed by legendary filmmaker Martin Scorsese, Goodfellas focuses on mid-level thugs rather than the bosses who pull the strings. It chronicles gangster Henry Hill’s (Ray Liotta) involvement with the local Mafia and was adapted from the true-crime book about his life, Wiseguy.
“How am I funny?”
Nobody plays a Mafia tough guy better than Joe Pesci. Here, the actor portrays Tommy DeVito, a trigger-happy psychopath with a short temper. The mood always gets tense whenever Tommy appears on-screen; you don’t know if he’s going to laugh with you or shoot you. He kills poor Spider (Michael Imperioli) during a card game just for talking back to him. He murders a “made man” over one of the most famous insults in cinema: “Now go home and get your f***in’ shine box!” And in the film’s most iconic scene, Tommy uses fear as a playful joke, asking his friend Henry (Ray Liotta) in a deathly serious voice, “How am I funny?” — though at the time, nobody realized that he was kidding, which terrified the entire group into silence.
Tommy is impulsive and reactional, a rabid animal with little self-control. Pesci’s frightening portrayal in Goodfellas won him the Oscar for Best Supporting Actor. But the most frightening part? His character is based on real-life gangster Tommy DeSimone, whom Henry described as a bona fide psychopath. Buy or Rent Goodfellas on Prime Video.
The Best Gangster Movie of Each Decade for the Last 100 Years
The gangster movie is one of film’s oldest genres and has been around since before the Golden Age of Hollywood.
1 Keyser Söze – The Usual Suspects (1995)
In The Usual Suspects, five criminals are brought together to pull off a heist for a mysterious crime lord. It was directed by Bryan Singer and features the likes of Stephen Baldwin, Gabriel Byrne, Benicio del Toro, and Kevin Pollack in its main cast. This 1990s thriller has become a classic since its release and features arguably the greatest plot twist in all of cinema.
The Greatest Trick the Devil Ever Pulled…
“Who is Keyser Söze?” That’s the question that we and the main characters are forced to ask ourselves during this movie. Keyser Söze is a crime lord that no one has ever seen or spoken to, save for the lawyer who claims to work for him. His existence is based only on tall-tales and gossip — and that’s what makes him so terrifying. Keyser Söze is the bogeyman of the criminal underworld, an urban legend that criminals like to tell each other in their prison cells late at night. But do you know what’s even more frightening? The fact that he actually does exist.
Keyser Söze (Kevin Spacey) isn’t a mythological figure but a ruthless gangster, a criminal mastermind who isn’t afraid of getting his hands dirty. He’s a brilliant strategist who can outsmart everybody else in the room. Even when he’s backed into a corner, with no escape in sight, Keyser will manipulate the situation and turn the odds in his favor. As Keyser famously tells us:
The greatest trick the devil ever pulled was convincing the world he did not exist. And like that… he is gone.
In this case, Keyser is the devil, using his cunning and deceit to take whatever it is that he needs from you. And before you even know what hit you — poof — he’s gone. Buy or Rent The Usual Suspects on Prime Video.