The Classic Gangster on Film

From Cagney to Costner to Bogart and Beatty, gangsters on film have been depicted in myriad ways. Whether it is in the classic or modern era of cinema, the portrayal of the classic gangster is fascinating.

Image Credit: Warner Bros.

Classic Gangsters on Film

Image Credit: Warner Bros.

From Cagney to Costner to Bogart and Beatty, gangsters on film have been depicted in myriad ways. Whether it is in the classic or modern era of cinema, the portrayal of the classic gangster is fascinating.

These ruthless people robbed and murdered, hell-bent on making a name for themselves to go against the proverbial “man” and live a life free from tradition and convention, but also rules and morals.

The motivation of the gangster stemmed from vanity and a determination to rise to the top in power, money, and fame. It was also often because many came from poor and humble beginnings.

Moreover, a culture disillusioned with the government and law enforcement due to the depressed financial times and rampant corruption found gangsters fascinating and were enamored by them and their lifestyles.

The “classic gangster” refers to the fictional characters and real-life men and women from the depression and prohibition eras in America, specifically the 1920s to the 1940s. When examining the cinematic gangster, it is interesting to see this type of figure’s varied looks and evolution as seen in various films.

The earliest films were often heavily stylized, especially in dialogue, and featured fictional gangsters often played by the same actors, namely James Cagney, Edward G. Robinson, and Humphrey Bogart. The films were stylized but truly reflected their personalities and motivations.

It is also important to note that because of the Hays Code, the censorship that affected early cinema made it so villains and corrupt characters could never get away with their crimes. Though not strictly enforced until 1934, some of the earliest pre-code gangster films still emphasized those parameters.

As time went on and the counter-culture era reigned in the 1960s and 1970s, the depictions of these gangsters shifted to morally gray or simply a straightforward look without necessary judgment. And finally, when we reach the modern era of film, the stylized, borderline noir gangster film shifts to more realistic and assuredly more violent examinations of gangsters.

Mostly depicting the real-life individuals of the era, these films also change in that they are not just about the gangster but also the lawmen who brought them down. Overall, the classic gangsters on film and how they evolved on screen are always interesting and entertaining. So let’s explore this evolution in cinema.

Image Credit: Warner Bros.

Little Caesar (1931)

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Image Credit: Warner Bros.

One of the earliest gangster films, Little Caesar, follows the rise and fall of Caesar Enrico “Rico” Bandello. A small-time crook looking to make more of his life joins the Vetorri gang in Chicago. Through his ruthless and charismatic nature, he quickly rises in ranks in the organization, taking over for Vetorri and then the higher-up Pete Montana.

“Rico” is vain and desires power above all else, murdering anyone who steps one foot in the wrong direction, including a newly appointed crime commissioner and a gang member who has a crisis of consciousness and could bring them all down. No one does anything without the approval of “Rico.”

But soon, his ego grows so large that he fails to see that his wise mantra of “the bigger they are, the harder they fall” that plagues his fellow hoodlums will also be his downfall.

In today’s society, the way we think of the classic gangster, the way they speak, act, and what they did, comes from a few specific actors and films from the 1930s. And Eddie G. Robinson and Little Caeser are most definitely one of them.

Robinson’s portrayal of “Rico” is the quintessential classic gangster whose speech is sharp and smarmy, demeanor viscous, and prowess leads to his defeat. With outstanding direction by Mervyn Leroy, this film is not only one of the first but also one of the most influential and essential films of its kind.

(Available on DVD and to rent on Amazon Prime)

Image Credit: Warner Bros.

The Public Enemy (1931)

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Much like Little Caesar, The Public Enemy, released the same year, is very much the quintessential classic gangster film that emphasized that what was depicted in the film was to be condemned. This film includes cards at the beginning and end of the film that says, The Public Enemy is essentially based on real people and the rampant problems of violent crime syndicates that terrorized various parts of the country.

They were a “problem” that needed to be dealt with, and this film is not glorifying their life in any way. On the contrary, it’s ever apparent how much this path leads to nothing but death, destruction, and heartache.

One of the most legendary “gangster” actors, James Cagney, stars as Tom Bower, a man who, along with his childhood best friend, goes from petty criminals to bootleggers and, in Tom’s case, murderer over many years.

Their wealth comes from threats of violence, and their arrogance and lack of morals and respect seep into their personal relationships. What’s important about this film is that it shows us that we do not always get second chances and that we often reap what we sow. The Public Enemy is also one of the most exceptional in portraying the theme of “crime doesn’t pay.”

(Available on DVD and to stream on HBO Max)

Image Credit: Warner Bros.

G-Men (1935)

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James Cagney turns in his gangster threads for that of a law enforcement officer or a “G-Man” in this 1930s classic. This tells the story of Brick Davis, a man who intends to become a lawyer but decides to join the force after his “G-Man” friend is gunned down, and he wants to help take down the gangsters who are wreaking havoc over numerous cities in the Midwest.

It’s a tale that balances suspense, tragedy, and romance with themes of integrity and courage. When the average moviegoer thinks of James Cagney, chances are they only remember his turns as the gangster himself. But Cagney as the lawman is not only just as effective, but the film itself is fantastic.

Moreover, G-Men is an ideal example of the filmmakers’ motivation not to glorify gangsters but showcase that they were an enemy to the public. The film’s re-release in 1948 also includes an introduction featuring a group of FBI agents being educated on the difficulties these men had in bringing these men to justice. This provides a modern audience with a sort of movie within a movie.

It also demonstrates where G-Men stands in the evolution of the classic gangster on film. It focuses on the law enforcement officers while also featuring the era’s style, making it one of the most unique ones on this list.

(Available on DVD and to rent on Amazon Prime)

Image Credit: Warner Bros.

Dead End (1937)

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The gangster as the primary focus takes a back seat in this dramatic film and instead shares focus with various characters on the dead end of a neighborhood that showcases the stark contrast between the wealthy and the poor. Located on the back side of an affluent apartment building, this tenement neighborhood follows these individuals as they all clash during a tense and, in the end, violent day.

There is the group of young kids who are all one wrong move away from reform school, or worse, a life of crime, otherwise known as the “Dead End Kids” and eventually “Bowery Boys,” who would go on to be featured in many more films.

There is the young woman who works hard to provide for herself and her younger brother, who is a part of this gang of delinquents. There is the kind and handsome but poor man (Joel McCrea), whom she loves, but he has eyes for another woman who longs for wealth. And there is the gangster who used to live there, “Baby Face” Martin (Humphrey Bogart), who returns to the neighborhood in his tailored suit. With his self-important and thuggish attitude, he hopes to be well received by his mother and former flame, only to be met with disdain.

What Dead End accomplishes is showcasing the juxtaposition of poverty and wealth, goodness and evil, and everything in between. Through these characters, we see how our choices define us, no matter our situation in life. And as far as the portrayal of the gangster, we see how they were so often born out of hardships but then corrupted into something dark and sinister.

Bogart plays a complicated man who longs for approval while not apologizing for his choices. It makes for a stark contrast to McCrea, who was once a juvenile delinquent himself but found his way towards a more prosperous life, not in money, but in integrity.

Directed by the great William Wyler, Dead End is a fascinating look at a specific time in history with themes that remain relevant today.

(Available on DVD and to stream on Amazon Prime)

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The Amazing Dr. Clitterhouse (1938)

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One of the most unique gangster films of the era, The Amazing Dr. Clitterhouse, once again stars Edward G. Robinson. But this time, Robinson does not play a gangster but rather a doctor who is fascinated with the mind of a criminal.

Researching on his own, Dr. Clitterhouse partakes in four solo robberies before infiltrating a gang, keeping his true identity and motives a secret. He connects with the gang’s leader Jo (Claire Trevor) and clashes with the gang’s heavy hitter, and most ruthless “Rocks” Valentine (Humphrey Bogart), as he helps plan another string of robberies in the name of research.

But as his involvement deepens, not only does the criminal life begin to fascinate him but also entice and intrigue him. Finally, when Valentine grows suspicious, he wants nothing more than to throw the doctor into the ocean with cement boots.

The performances are captivating in this unconventional classic gangster film that examines how people of the era could so quickly become enamored with these criminals and the art of the crimes themselves. Dr. Clitterhouse’s research reaches far beyond his initial scope, resulting in an intriguing examination of the life, and most especially the mind of the gangster.

Like an addiction, it gives them a quick fix that needs to be repeated, and it becomes its own drug, corrupting the body and mind. Moreover, this film takes some unique turns focusing on the consequences of misplaced confidence and what only the darkest criminals are capable of.

(Available on DVD and to rent on Amazon Prime)

Image Credit: Warner Bros.

High Sierra (1941)

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The gangster life in the big cities of the east is replaced with a more intimate look at a former gangster’s life after being pardoned and released from prison in the Western part of the United States.

In this John Huston-directed film, Humphrey Bogart plays Roy Earle, a notorious former gangster who, despite being pardoned, goes right back into the life of crime, wanting to make one big score that will set him up for life.

Under the instructions of his former boss, he meets up with a gang of fellow criminals, including two hot-headed men who need his guidance and a tough and forthright woman (Ida Lupino) who takes a keen liking to Earle. The plan is to rob a luxury hotel and split the take, but things do not always go as planned.

Teetering the line between the typical gangster film and the noir films of the 1940s, High Sierra is rich with remarkable character studies, most especially with Earle’s character. Without a doubt, he is a brutal man willing to murder and shows little remorse for the demise of his fellow comrades.

But Earle is also a complex man. He turns out to be much more of a morally gray character than gangsters of the past. Earle often displays glimpses of a softer and more sympathetic side, seen not only in his relationship with Lupino’s character, but also with a sweet young woman he meets and wants to marry.

This showcases a unique tale and highlights the start of the evolution of these types of films. Roy Earle is not a hero but also a character with unexpected depth.

(Available on DVD and to rent on Amazon Prime)

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Key Largo (1948)

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One of the finest films that featured the legendary pairing of Humphrey Bogart and Lauren Bacall, Key Largo is a fantastic film and the perfect transition in the evolution of gangsters in cinema. The movie follows Army veteran Frank McCloud (Bogart), who visits the father and widow Nora (Bacall) of his fellow soldier at a hotel in Key Largo, Florida, only to find mobsters “in charge.”

And therein showcases why this is a transitional gangster film. Hiding out in this hotel is the aging Johnny Rocco (Edward G. Robinson), his hired muscle, and former flame, the alcoholic moll Gaye Dawn (Claire Trevor). With the height of their terror and prohibition over, Rocco wants to relive his former glory. He is determined to prove he can still control and do anything he wants under the threat of intimidation and violence. When a hurricane fast approaches, all of these characters are forced together, and they must see what they are made of.

Excellent drama and terrific performances abound. Key Largo represents the time in cinema when the gangster is no longer in their heyday, but the fear they can illicit remains. Additionally, director John Huston showcases that this fear pales in comparison to true bravery and that these men no longer had the power they once had.

Rocco represents the gangster still living in the past who wants to be revered. In the end, as with all films at this time, this evil is defeated, and goodness and bravery triumph.

(Available on DVD and to stream on HBO Max)

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Bonnie & Clyde (1967)

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Bonnie Parker and Clyde Barrow are arguably the most recognizable and popular gangsters in American history. When the two meet, Bonnie is a poor waitress bored with her life, and Clyde is recently released from prison on “good behavior.” But unfortunately, that good behavior does not last long. The man in prison for armed robbery returns to it mere minutes after meeting Bonnie, and the two begin a crime spree across the Midwest.

Along the way, the Barrow gang soon also consists of an easily taken-in and gullible simpleton, Barrow’s brother and sister-law. With bank robberies, shootouts with law enforcement, car chases, and a famously very violent end, the public revered Bonnie and Clyde as carefree figures who only robbed banks, not people.

The media perpetuated the mythos behind the infamous duo, and by the time the 1967 film came out, and the counter-culture permeated the film industry, that mythos only grew.

Depicted as a love story, Bonnie and Clyde were given an air of sympathy with a film focusing more on style than truth. There is minimal accuracy to the actual figures who freely murdered not only policemen but also innocent people and often robbed small establishments in addition to banks. Their film personas are good-time bandits instead of the sociopaths they were.

The view into their lives mirrors the odd fascination and reverence the everyday folk of the time held for the pair, depicting, in that case, some semblance of accuracy. Each era (both the one shown in the film and the one in which the film was produced) therefore feels synonymous with how people somehow loved and admired the duo.

Bonnie and Clyde the film and Bonnie and Clyde, the individuals, are quite different from each other, but the movie remains a captivating one.

(Available on DVD and to stream on HBO Max)

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The Godfather Saga (1972-1990)

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Image Credit: Paramount Pictures.

Francis Ford Coppola’s powerful, immersive, and endlessly absorbing films about an Italian mobster family from the early 1900s to the 1960s are understandably lauded as some of the greatest films of all time.

And in the evolution of the gangster on film, The Godfather films represent that bridge between the earliest films and the modern era of cinema.

Following the Corleone mafia family, the first film centers on the aging patriarch “Godfather” Vito Corleone reluctantly passing control of their business to his youngest son Michael, who becomes just as vicious as his father.

The second film flashes back and forth between the present and Vito’s back story, showing how his beginnings were altruistic before they snowball into the violent crime syndicate they become. And in the third film, Michael attempts to break free from the life of crime and legitimize the family business but struggles to do so.

What’s interesting about The Godfather trilogy is that these films are not necessarily labeled as “gangster” films but rather family dramas, which is undeniably true. These films depict the brutality of the mafia but how the family is what matters to them the most. Power is paramount but crossing the family is the greatest sin.

Consequently, this stage in the aforementioned evolution of the gangster movie shows the breadth of their crimes without necessary condemnation. It’s up to the audience to judge and, in the end, focuses more on a story about family.

(Available on DVD and to stream on Paramount+)

Image Credit: Paramount Pictures.

The Untouchables (1987)

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Very loosely based on Eliot Ness’ autobiography that also inspired an earlier television series of the same name, The Untouchables is a brilliant representation of that shift in focus from the gangsters to those whose task was to bring them to justice.

The prohibition era tale follows Agent Eliot Ness (Kevin Costner), who, because of the widespread corruption in the Chicago police department, takes it upon himself to assemble a team to take down notorious crime boss Al Capone. Ness and his team work tirelessly and courageously to bring the gangster to justice, with their very lives on the line at all times.

Evolving from the classic era, The Untouchables highlights the brave lawmen who were some of the few who had not been tainted or corrupted. It also honors these men who helped to bring down one of the most vicious mob bosses in history. Moreover, The Untouchables gives us a genuine sense of the gravity of Capone’s over-reach and the rawness of the danger these men put themselves in the center of.

Overall, the film is not only rife with a more realistic approach but also remains entertaining, thanks to a distinct tone from director Brian De Palma and exceptional performances from the likes of Costner, Sean Connery, Robert De Niro, and Andy Garcia.

(Available on DVD and to stream on HBO Max)

Image Credit: Paramount Pictures.

Bugsy (1991)

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Image Credit: Tristar Pictures.

The tale of the brutal gangster Ben “Bugsy” Siegel is brought to rich and captivating life by director Barry Levinson and actor Warren Beatty. With his long-suffering wife and daughters in New York, Bugsy travels to Los Angeles, in no hurry to return home.

He aims to build up his crime syndicate and becomes enamored with the Hollywood life, especially the actress Virginia Hill, whose personality is just as aggressive as his. He becomes associated with the equally vicious Mickey Cohen and is one of the first people to bring a gambling hotel to Las Vegas, the building of such becoming his obsession and downfall.

Siegel is vain and desires popularity, and wants to be seen as dapper and gentlemanly. He dresses the part, while simultaneously showing no hesitation in murdering or brutally beating anyone who dares to steal or double-cross him. In the timeline of the evolution of the gangster on film, Bugsy is a straightforward and mostly accurate look at life in 1940s Los Angeles.

The film has exquisite period fare and a sense of glamour juxtaposed against the violent, albeit exciting life of one of America’s most notorious gangsters. And the murder of Ben “Bugsy” Siegel remains one of the great unsolved mysteries to this day.

(Available on DVD and to stream on Amazon Prime)

Image Credit: Tristar Pictures.

Public Enemies (2009)

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Image Credit: Universal Pictures.

The life of gangster John Dillinger (Johnny Depp) is the film’s focus, which portrays glamour contrasted against the harsh and downtrodden climate of the era. Known for his good looks, fashionable style, love of women, movies, and bank heists, Dillinger is cold and calculating one moment and warm and charismatic the next.

He is indulgent, arrogant, passionate, and violent when push comes to shove. In his mind, he is not stealing from innocent people or hurting anyone for pleasure. The truth isn’t so innocent, but still, it’s a stark contrast to fellow gangster of the time “Baby Face” Nelson, who seemed to take pleasure in excessive violence, and meets a grisly end as a result.

One of America’s most infamous gangsters in history, the end of Dillinger’s life is well known, but what leads up to it is captivating to watch. Depp portrays Dillinger with appropriate charisma and a sense of underlying malevolence that can be triggered at any moment in this straightforward biographical drama that neither condemns nor condones the life of the gangster.

It’s clear this is no glorification of Dillinger, but at the same time provides the audience with some relatable moments and an engaging look at this man’s life.

(Available on DVD and to stream on Netflix)

Image Credit: Universal Pictures.

Gangster Squad (2013)

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Much like The Untouchables, Gangster Squad boasts an impressive cast including Josh Brolin, Sean Penn, Ryan Gosling, Emma Stone, Nick Nolte, and Anthony Mackie, and strives for a balance of realism and panache, and focuses on the lawmen bringing down a crime syndicate rather than strictly the gangsters themselves.

Inspired by the actual events, this tells the story of Sergeant John O’Mara (Brolin), who assembles a team in 1940s Los Angeles to take down the mobster Mickey Cohen (Penn) and the other slew of gangsters who terrorize the city. This includes the reluctant Sergeant Jerry Wooters (Gosling), who joins the team after he sees a young boy murdered at the hands of Cohen’s men and becomes romantically involved with Cohen’s dialect teacher and girlfriend Grace (Stone).

Similar to Bugsy, this is a stylish period film filled with the truth of the sadistic nature of gangsters and the violence that ensues. Firmly in the modern type of “gangster” film, this may not feature the moralistic tone that the 1930s films employed, but make no mistake, this is about the squad that took down Cohen seen through a virtuous lens. The film may not be historically accurate in every sense of the word, but it captures the era beautifully and the story captivatingly.

(Available on DVD and to stream on HBO Max)

Image Credit: Warner Bros.

The Highwaymen (2019)

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A gritty, gripping, and relentless tale, The Highwaymen is about officers Frank Hamer and Maney Gault, otherwise known as the reinstated Texas Rangers, who pursued and gunned down the infamous gangsters Bonnie and Clyde in the 1930s.

Most assuredly, this film is the antithesis of 1967’s Bonnie and Clyde, with director John Lee Hancock’s motivation for making this film to tell a realistic and historically accurate story about these men and what Bonnie and Clyde were truly like.

Unlike the 1960s tale of carefree bandits, the pair, although barely seen on screen, is more accurately depicted as the violent murderers they were. Moreover, while the 1967 film portrayed Hamer as somewhat incompetent, The Highwaymen shows Hamer and his partner Gault as brave, intelligent, and tireless in their pursuit.

This film is not only entertaining but is an example of how to create a stylish, authentic film portraying the gangster for who they were in reality. The Highwaymen also represents the current place in the evolution of the gangster on film, and it does not shy away from the violence or rawness of the depressing time and gangster lifestyle.

Thanks to the performances by Costner and Harrelson and the direction of Hancock, the daunting hunt for the Barrow gang depicted in The Highwaymen is both rife with stark realism and enthralling drama.

(Available to stream on Netflix)

Image Credit: Netflix.

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Marianne Paluso is a freelance artist and writer inspired by her favorite films, television, theme parks and all things pop culture. She especially loves Disney, classic films, fairy tales, period dramas, musicals, adventures, mysteries, and a good rom-com. She also partakes in the occasional Disneybound, cosplay, and YouTube video.