Movies about gangsters and the lives they live have always fascinated audiences and made for some of the most highly acclaimed pictures in history. Such is the interest around these figures, whether they be fictional or not, that the careers of many actors and directors have become synonymous with the genre and the reason for much of their success.
Try thinking of Martin Scorsese or Robert De Niro, and it's likely that films like Casino or The Irishman will immediately spring to mind, just as the names Brian De Palma or Al Pacino inevitably conjure up images from Scarface or The Untouchables. Glamorized by Hollywood, the lifestyles of gangsters, no matter how reprehensible they may be, have also always held a morbid appeal. As much as ordinary, law-abiding citizens may hate to admit it, the lives of some gangsters, in real life and on-screen, have some truly attractive qualities.
Between the money, power, and influence they wield, gangsters often come across as cool, despite them actually being the villains. In homage to those gangsters over time whose on-screen portrayals have captivated audiences time and time again, here's a ranked list of the coolest gangsters in movie history.
Updated on August 5th, 2023, by Danilo Raul: This article has been updated with additional content to keep the discussion fresh and relevant with even more information and new entries.
20 Tony Soprano
The Sopranos (1999-2007)
Tony Soprano is the quintessential XXI-century Mafioso. He was brilliantly played by James Gandolfini, who turned up the performance of a lifetime in The Sopranos, a role that would bring him multiple awards. We meet Tony in what should be the best moment of his life. Although his elder uncle Junior Soprano is next in the line of succession to lead the family, everyone knows who runs the game in New Jersey. Tony is an accomplished man with multiple business fronts and a loving family, but nothing is enough for him.
Tony seeks the help of a therapist on account of his panic attacks due to multiple unresolved issues with his later father and his ruthless mother. Guys from the old regime begin to return from their stints in prison, and they are coming back to a world that no longer welcomes their kind. His family secretly hates him. As the show advances, we slowly realize that Tony is inheriting a falling kingdom, and all he can do is try to hold the pieces together as corporate America takes over, leaving the mob as a thing of the past.
19 Murakawa
Sonatine (1993)
Takeshi Kitano was a longtime comedian in Japan with dreams of becoming an international superstar. It took a left turn in his career to gain his desired recognition. Kitano is known for playing hardened criminals in most of his films. His understanding of Yakuza culture allows him to explore the human side of the underworld in very unsuspecting ways. His role as Murakawa in Sonatine it's one of his finest performances to date.
Murakawa is a solemn, stoic Yakuza who grows tired of the criminal life. His Oyabun sends him on a special assignment to settle a dispute between rival gangs. Suspecting he's being set up to be assassinated, Murakawa walks into the trap, only to have most of his men killed in a planned bombing. After hiding in an abandoned beach resort, he finds out his boss is making a deal with a rival to take over his turf. He finds out the location of the meeting and kills them all. Slick and easy.
18 Tom Powers
The Public Enemy (1931)
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It was challenging to separate James Cagney from the old-school gangster stereotype after this film was released. In The Public Enemy, Cagney plays no-nonsense gangster Tom Powers, a man who gains the favor of a local mobster Samuel "Nails" Nathan, during the prohibition era in Chicago. Tom gains power, money, and respect as a handler for Nails, but his family rejects him, especially his brother, who returns from serving in the First World War.
As the story advances, we see Tom fall deeper into the clutches of the underworld as rival gangs target him. With his friends and mentor dying left and right, the mentally unstable Tom is ready to go on a violent rampage. Still, he quickly stopped after his family decided to take him in again. Sadly, the underworld is unwilling to forgive his sins so easily. When Tom finally returns home, his brother is there to receive him and perpetuate the cycle of violence.
17 Mark Lee
A Better Tomorrow (1986)
Chow Yun-Fat might seem like a minor celebrity in America, but in his native China, he's a massive star. He got his big break with the first pairing with John Woo in A Better Tomorrow. Yun-Fat plays the role of Mark Lee, the enforcer, bodyguard, and best friend of a Triad accountant named Sung Tse-Ho. Being in such a position of power, Sung can provide for his family and send his little brother to the Police Academy. Sadly, his brother discovers his dealings with the Triads and disowns him from the family.
Mark stays a friend with both men, trying to ease the tension between the brothers. When Sung is imprisoned after being captured and laundering money, the Triads try to kidnap his dad to ensure his silence, killing him in the process. Mark waits for his friend to come out of jail and pairs up with him and Sung's brother to wreak havoc and destroy every member of the Triad who messed with his friends. This film launched the career of Yun-Fat and was the first of five collaborations with the famed director.
16 Frank Lucas
American Gangster (2007)
Frank Lucas used his wits and street smarts to cut out middlemen and forge a drug trafficking empire for himself out of Harlem, New York. This was no easy feat for an African American at the time since the Italian Mafia pretty much ruled all underworld trade in the city back then.
An imperious Denzel Washington aptly played him in the film American Gangsterwhich was nominated for two Academy Awards. Washington perfectly captured the kind of struggle that Frank Lucas went through to build his empire and the swag with which he lived his fascinating life — a life made even more fascinating by the fact that it was all true.
15 II Duce
The Boondock Saints (1999)
The 1999 small-budget film The Boondock Saints became an instant cult classic as it took on themes of gangsterism and what happens when two people decide to stop turning a blind eye to the atrocities of the mob. The mob in question in the film was the fictional Yakavetta family. When a pair of vigilante brothers decide to take on this powerful family, in desperation, the Yakavetta family turns to an almost mythical figure to stop them. Known as II Duce (The Duke), he was only hired three times in 30 years since he was the kind of person you only used as a last resort.
Even now as an old man, Il Duce was so deadly that the aftermath of his exploits led investigators to believe that there were six shooters involved in a shootout he caused — when in fact it was just one man with six guns. His entire presence and aura in the film were cool from the moment he shows up. By the end, he teams up with the vigilantes himself, who turn out to actually be his sons. In a film full of awesome lines, Il Duce gives one of the best ones as he chats to one of his sons about how far they are going to take their vigilante justice against the mob.
14 Henry Hill
Goodfellas (1990)
With a 96% approval rating on Rotten Tomatoes to date, Goodfellas was another one of those unforgettable gangster movies by Martin Scorsese. At the helm of this one was Henry Hill (played by Ray Liotta) who becomes enamored by the lifestyles of gangsters as a kid and later works his way up the ranks to become one himself.
As an adult, Hill takes to life like a fish to water and is pretty soon looking and dressing the part and running his own rackets. Hill poignantly displays the fascinating side of power in one of the film's most memorable scenes. When a tough guy from her neighborhood harasses the girl he fancies, Hill walks right up to the guy in broad daylight and pistol whips him in front of his two friends without saying a word, knowing that as a 'goodfella,' he's virtually untouchable.
13 'Johnny' Tapia
Bad Boys II (2003)
The Bad Boys franchise from Michael Bay may have centered around two buddy cops, but there were also many other memorable characters from the films. One such character was definitely 'Johnny' Tapia who kept law enforcement and rival gangsters chasing their own tails in Bad Boys II for practically the entire film.
As a Cuban drug lord, Tapia wielded enormous power, wealth, and influence, and used it to devastating effect against anyone who crossed him. The quiet confidence he often exuded made him a character that oozed coolness in many ways for the way he could handle his business. Of course, the Bad Boys always get their man, but that wasn't before Tapia left an indelible mark on the film with gangster charm.
12 Donnie Brasco
Donnie Brasco (1997)
Former FBI agent Joseph Pistone probably had one of the most fascinating careers out there. For five years he infiltrated the Bonanno mob family as an undercover agent using the name 'Donnie Brasco' and eventually worked his way up to the point of being a made man. In 1997, the film Donnie Brasco portrayed Pistone's time with the mob and how deep undercover his role took him. The film was a stark reminder of just how blurred the lines can become between the real world and the world that gangsters inhabit.
Played by Johnny Depp, Brasco's harrowing ordeal was brilliantly captured, from the swagger he developed as his gangster alter ego, to the very real dangers he faced every day of his life in those moments. Again, what makes this so cool and even more appealing was that, despite it being a stranger-than-fiction kind of tale, it was all true.
11 Frank White
King of New York (1990)
Christopher Walken is a screen legend and one of the most memorable roles that earned him that reputation was his portrayal of a gangster named Frank White in King of New York. White was a drug kingpin who, upon his release from prison, has to rebuild his business.
What made Frank White so cool was the apparent fearlessness and determination with which he sets about doing this. Personally ensuring that he takes out his competition, he takes on Colombian drug cartels and Triad members, seemingly without a care. White shows that he is ruthless as he fights for every scrap he feels entitled to until the very end.
10 Walter White
Breaking Bad (2008-2013)
Rarely in the history of television has there been a character who inspired as much cult popularity as Walter White. The lead character from the legendary show Breaking Bad, White's transformation throughout the show was mind-bending. Played by Bryan Cranston, the fact that he started off as a harmless chemistry teacher and family man made it all the more jaw-dropping. The reason — by the end, Walter White became one of the most feared and respected drug lords in the country.
What he lacked in brawn, he more than made up for with the fierce and deadly intellect that he used to outwit and murder many people, including rival dealers, cartel assassins, and anyone else that got in his way. His style and quiet confidence made him one of the coolest gangsters in TV memory and cemented Breaking Bad as one of the greatest shows ever made.
9 Nicky Santoro
Casino (1995)
Despite Joe Pesci's small size and sometimes comical demeanor, as a gangster, he never fails to make for one intimidating figure. This was never more evident than in the hit Scorsese film Casino. Starring alongside Robert De Niro, Pesci played Nicky Santoro, the borderline psychotic gangster tasked with helping De Niro's character enforce the Casino business they were handling for the mob.
Santoro's unhinged and volatile nature throughout the film made him a real live wire. In any given scene he was in you never knew if it would end with him cracking a joke or in bloodshed. Aside from his violent tendencies, he also proved himself to be quite a manipulative character which somehow only added to his morbid charm. In the end, Santoro's unpredictability even became too much for the mob itself, and he paid the ultimate price for it.
8 The Kray Twins
Legend (2015)
Ronald and Reginald Kray were legendary figures of the London gangster scene between the '50s and '60s. Identical twins, they could not have been more different in other ways. Using violence, intimidation, and influence, the twins all but ruled parts of London for a long time. They became nightclub owners and lived an almost celebrity-like lifestyle for a while. While one was cold, measured, and ruthless, the other was unpredictable and probably more than a little psychotic.
In the 2015 biopic Legend,the twins were both brought to life spectacularly by Tom Hardywho played them both in the movie. The vast differences between them made for a stunning display of Hardy's acting range as the coolest and most ruthless elements of the twins' lives were portrayed with the kind of flair and style that only an actor of Hardy's quality could muster.
7 Michael Corleone
The Godfather (1972)
Michael Corleone may have been a fictional character from Mario Puzo's legendary novel (turned legendary film series) The Godfather but his status as one of the coolest gangsters in history isn't affected by this fact. Played by Al Pacino in the films, Corleone was ranked as the 11th most iconic on-screen villain by the American Film Institute.
What made him cool wasn't just the fact that he became the head of one of the most powerful mafia families, but everything he achieved before this. He initially wanted nothing to do with the family business. As a result, before taking over he attended Dartmouth College, was a marine, fought in the Pacific War, and rose to the rank of Lieutenant. After his father's death, he reluctantly takes over the family business and cemented himself as one of the coolest gangsters in movie history.
6 Frank Costello
The Departed (2006)
Another masterpiece from Martin Scorsese, The Departed was as gritty and brilliant a gangster film as you'll ever see. As the head of the South Boston Irish mob, Frank Costello (Jack Nicholson) made for one complex character. He was ruthless, as intimidating as they come, and could back it all up with his power and reach.
However, he also proves throughout the movie to be a brilliant tactician. He constantly stayed one step ahead of law enforcement and kept them running in circles as he even went as far as to infiltrate their ranks with his own men. His layers meant that he could be cold and violent, charming and funny, and even philosophical at times, always keeping a cool edge of confidence to everything he says and does.
5 Pablo Escobar
Narcos (2015-2016)
Perhaps the most famous and vicious gangster in history, the name Pablo Escobar is both legendary and infamous. Possibly one of the most feared and ruthless criminals that ever lived, Escobar's enterprises in Cocaine production and distribution shook the world and continue to do so long after his death. At his peak, he was so powerful that he took out Presidential candidates and scores of other people that got in his way, was one of the richest men in the world, and even attempted to run for President of Colombia himself.
He is still hailed as a godlike figure today and is revered among the most powerful drug cartels in the world. For sheer power and influence, Escobar has always been portrayed as one of the coolest and most vicious gangsters in history. There have been many depictions of him in films and TV. Most notably in recent times, Netflix's hit show Narcosdedicated its first two seasons to Escobar and provided a chilling rendition of his true life exploits.
4 Don Vito Corleone
The Godfather (1972)
The original Godfather, Don Vito Corleone's portrayal by Marlon Brando has forever become one of the most legendary performances in movie history. Brando actually stuffed his cheeks with cotton wool to achieve the distinctive voice and look of Corleone as he spoke.
The head of his own incredibly powerful mob family, Corleone's lines throughout the first Godfather film are timeless. While the role was later taken over by Robert De Niro, Brando's original performance set the benchmark for the ultimate gangster role and has probably never been surpassed since.
3 Al Capone
The Untouchables (1987)
Al Capone is a legendary figure whose life and legacy are sometimes hard to believe. In some ways, he was the original gangster as he forged an empire with his Chicago operations that were known for being ruthless. Capone's exploits were the gold standard in gangsterism as his rackets made him insanely rich while his power and influence made him feared and despised by law enforcement.
He suffered a lot of mental and physical setbacks in his older age but before that, rose to become an almost mythical figure as far as crime lords go. While Tom Hardy's portrayal of his later years was certainly brilliant and disturbing in Capone, his most famous portrayal was in Brian De Palma's The Untouchableswhere Robert De Niro took on the iconic role in a brilliant film about the rise and fall of Capone and his empire.
2 Tony Montana
Scarface (1983)
Brian De Palma's success with The Untouchables came four years after he had already become a legendary director for another gangster film. That film was of course the unforgettable Scarface. Al Pacino's most famous roles often fluctuate between his turn as Michael Corleone and probably his most iconic role as Tony Montana in Scarface.
The film and Tony Montana's exploits in it have become legendary with quotes and references to it showing up everywhere in pop culture since. Montana was a Cuban refugee who rose to become a powerful and homicidal crime lord. His swag, mannerisms, and demeanor oozed cool throughout the movie and even in his final moments, Montana went out with style. His famous line, "Say hello to my little friend," is one that never gets old, just as the character and Pacino's performance remain legendary to this day.
1 Sam 'Ace' Rothstein
Casino (1995)
The 1995 gangster flick Casino is one of Martin Scorsese and Robert De Niro's most famous. Telling the sweeping rise and fall of a mafia associate known as Sam 'Ace' Rothstein, the film is a brilliant rendition of the excesses of the mafia lifestyle, and just how tangled a web their operations often became. Tasked with running the Chicago Mob's Tangiers Casino in Las Vegas, Rothstein quickly proves himself competent and a huge moneymaker for the mob. However, the lifestyle and the mob's interests are never that straightforward and problems quickly escalate.
Throughout the film, Rothstein's suave and calmly measured personality, coupled with his brilliant eye for gambling, makes him one cool character throughout the film. His only downfall is the trust he places in his wife (played by Sharon Stone) and his enforcer Nicky Santoro (Joe Pesci). Despite all the problems that arise, Sam keeps his head throughout and manages to survive it all despite the danger all around him. His ice-cool demeanor and the style he exudes throughout the film have made De Niro synonymous with cool gangster films — a trope epitomized by his brilliant performance as Sam 'Ace' Rothstein.