Top 10 Must Watch Classic Gangster Films

Gangster flicks are a unique breed of film. The narratives often force audiences into a kind of ethical dilemma. Though “gangsters” break the law, they are nevertheless endearing. Audiences have no choice but to pull for the dastardly or morally dubious gangsters they see on screen. As with any noble transgressor, gangsters in film invert the moral structure of society. On the one hand, they do in fact commit crimes and break the law, which has ostensibly been created for the betterment of society and the protection of rank-and-file denizens. However—and herein rests the eternal truth about any rule-breaker—the gangster can also be construed as the revolutionary, opportunist, or anti-hero who fights an oppressive and unjust force—the law, poverty, institutional discrimination, specious rules, etc. Seen in that light, the gangster is less dubious than admirable.

Francis Ford Coppola’s masterful classic, The Godfather, which he adapted from Mario Puzo’s bestselling series of the same name, attests to this latter point, as Vito Corleone overcomes painful poverty and the untrammeled malevolence of local mob bosses, becoming the leader of his own criminal organization. His ascendancy in the world of crime affords his family the freedoms and liberties that the Founding Fathers espoused when they signed the Constitution. As such, The Godfather is profoundly American and echoes the American meta-narrative: the “Land of Opportunity.”

But not all gangster films are created equally. Some films celebrate both immorality and amorality, as characters flaunt their iniquity. These types of films often make a spectacle out of crime and murder. Instead of crime representing a necessary act for the protagonist, it loses its symbolic power in these films and, in a carnivalesque sense, fascinates the viewers who, for two fleeting hours, can participate in acts they would never dream of committing in real life. This fetishization of crime and violence binds the audience to the characters on screen, if only because, as witnesses, the audience partakes in these acts of iniquity.

Quentin Tarantino’s Reservoir Dogs, for instance, features a host of characters who are morally corrupt and irredeemable. The scene in which Michael Madsen’s character ruthlessly tortures a police officer is utterly void of propriety and morality, but for those very reasons, it fascinates viewers. With its balance of unreality and shockingly real brutality, the scene is a cathartic spectacle for audiences who have long suppressed their id-like urges and cravings. It’s not that audiences secretly want to kill police officers, but Madsen’s irreverence and flippant dancing as he tortures the officer fills a temporary void in audiences’ lives—a void that is inexplicable and intangible, but often finds its transitory fulfillment in curse words and other improprieties.

As this opening has already intimated, this list looks at ten classic gangster films. Whether these films feature noble anti-heroes or corrupt, yet compelling evildoers, they are all notable for being acclaimed and extolled by critics and viewers. There are notable gangster films missing from this list, but the list has tried to balance familiar classics with films that North American audiences might not be familiar with. In any case, let us know your favourite gangster films in the comments section. As always, enjoy…

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10 The Godfather (entire series)

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After being mentioned in the opening, The Godfather had to be on this list. Francis Ford Coppola’s timeless classic is one of the finest film trilogies ever produced. As fans of the trilogy know, Part 3 is decidedly weak in comparison to the other two and somewhat tarnishes the other films’ excellence. What the first two films get absolutely right is pacing. Indeed, from the highs and lows of organized crime to the shocking character developments and plot twists, the first two films keep audiences immersed without burning them out. Marlon Brando masterfully plays Vito Corleone in his later years. Vito, above all, wants his family to be happy, but his eldest son’s impetuosity and pugnacity attract the wrong kind of attention. Al Pacino plays young Michael Corleone with poise and assurance, and the film series is interesting, if only to follow Michael’s development from conscientious objector with regard to his father’s business to hardened crime boss who desperately wants to expiate his sins. The Godfather will continue to amaze generations long after the people who made it are gone.

9 Casino (1995)

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Featuring a star-studded cast, and masterfully directed by Martin Scorsese, Casino is one of the lesser known gangster films in recent memory. Two mobster friends—Pesci and De Niro—fight for control of a criminal empire with a casino in its midst, and they also butt heads for possession of a beautiful trophy wife. Greed, deception, betrayal, and immorality pervade this film, a film that takes viewers on a roller-coaster ride through the rapturous highs and devastating lows of organized crime. Fans of Scorsese and mob movies in general should not miss this one.

8 Goodfellas (1990)

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From Henry Hill’s (Ray Liotta) opening admission—“As far back as I can remember, I always wanted to be a gangster”—to his final decision to betray his own crime syndicate in exchange for his freedom, Goodfellas is compelling and fascinating. The Oscars notably snubbed Martin Scorsese for Best Director in 1990, a still-puzzling decision. The film decidedly hits the mark in every area.  The acting is brilliant, and the characters—namely those played by Robert De Niro, Joe Pesci, and Ray Liotta—have an excellent repartee throughout. Audiences cannot help but feel compassion for Henry, a man seduced by the criminal world in which he grew up and who wants to extricate his family from the dangerous world of the mafia. Style—namely, the era-specific music and dress—pervades this film, and, up until the final thirty minutes of the film, the mafiaso’s life has never looked so alluring.

7 Scarface (1983)

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In Scarface, Brian De Palma’s unforgettable crime epic, Al Pacino plays Tony Montana, an indigent Cuban immigrant who descends into the sordid world of murder and drug dealing to create a life for himself and his family in America. Al Pacino is surprisingly good as a Cuban in this film, and his performance makes audiences forget that he is also Michael Corleone. But like The Godfather, this eighties classic reflects the American meta-narrative that has inspired so many foreigners to immigrate to America. Montana, though, finds his opportunity in a world of crime, and his ascent and subsequent descent make a compelling narrative.

6 Once Upon a Time in America (1984)

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Known for his masterful epics, Sergio Leone directs Once Upon a Time in America, a film that tells the story of a Jewish gangster during Prohibition and, subsequently, during his return to New York in the 1960s. Robert De Niro and James Woods play their roles well, bolstering this episodic narrative. Its treatment of time is the highlight of this film, as it shuttles between various time periods and does not end where audiences think it will. Like many of the films on this list, this one does an amazing job of charting the vicissitudes of mob life, a life that most certainly contains a good deal of peaks and valleys.

5 Donnie Brasco (1997)

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Another film on this list with Al Pacino, Donnie Brasco tells the story of Joe Pistone (Johnny Depp), an undercover cop whose job is to infiltrate the Mafia. Depp’s character soon develops a kind of Stockholm Syndrome-like compassion for Sonny Black’s lackey, Lefty Ruggiero (Pacino), whom he spends his time with. Mike Newell does a fabulous job of directing this well-paced drama that puts viewers abreast of Pistone as he tries to make his decision between right and wrong, a decision that becomes increasingly less clear-cut as the narrative develops. Like so many of the films on this list, this one nails the feeling of the era in which it is set, and the actors are all at their best.

4 Miller’s Crossing (1990)

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Goodfellas wasn’t the only incredible tale of gangsters released in 1990, as this film surprised audiences and laid the foundation for the future success of then-unknown collaborators, Joel and Ethan Coen. Similar to Once Upon a Time, Miller’s Crossing takes place during Prohibition, a time that was fecund for organized crime and dastardly dealings. Like many of the Coen brothers' early films—namely, Barton Fink—the narrative is nihilistic, and viewers struggle to find redeeming qualities in the characters. Ironic comments, quirky characters, and shocking violence, as is the brothers' wont, pervade the narrative.

3 Sonatine (1993)

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Starring and directed by Takeshi Kitano, Sonatine is a poignant tale of betrayal within Japan’s world of organized crime. However, though betrayal fuels many of the events in the narrative, it would be reductive to call it a narrative solely about that. Indeed, when Kitano’s character retires with his close-knit associates to the countryside to figure out his next move, the narrative becomes less a gangster film than a dialogue-driven film set on the beach. It would be erroneous to call this narrative the gangster pastoral, since real fear fuels the excursion to the beach. That said, the film is captivating for its beach scenes through which audiences discover the humanity within these morally questionable characters.

2 Reservoir Dogs (1992)

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Since this film, Quentin Tarantino has gone on to become one of the industry’s most influential and daring directors, but Reservoir Dogs might just be his magnum opus. Legend has it that Harvey Keitel had to kick in a good deal of his own money to make this film a reality—without which the film would have floundered due to lack of financial support (Thank you, Harvey Keitel). The premise is simple: a wealthy crime boss assembles a motley crew of criminals to pull off a big heist; the heist, as the audience can infer, goes horribly wrong, and the aftermath is the stuff of the film’s narrative. The audience soon learns that there is a rat within the group, who tipped the police off before the disastrous heist. As the various characters try to winnow out the rat from the group, audiences are treated to a shocking amount of violence. As mentioned, the Michael Madsen-torture scene is the film’s highlight.

1 Infernal Affairs (2002)

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Did you like Martin Scorsese’s The Departed? If so, you will likely enjoy this film and maybe grow to appreciate it more than Marty’s hit. That is because The Departed is almost a shot-by-shot remake of Infernal Affairs. Directed by Wai-Keung Lau and Alan Mak, Infernal Affairs tells the story about opposing parties—cops and robbers, essentially—desperately trying to uncover the identity of the mole that they have each planted in each other’s midst. The film is thrilling without being overblown, and hits on all the high points that viewers will remember from The Departed. Moreover, in the narrative, a novelist, who is the inamorata of one of the moles, is writing a novel but has trouble with the ending. This “trouble with the ending” echoes the uncertainty of her boyfriend’s fate, adding some symbolic sophistication to an otherwise action-packed narrative. Fans of The Departed, go and see this film.

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