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Greatest Gangster Movies

Offering tons of real stories about the mob, the greatest gangster movies are pure entertainment and excitement.

By Bethany TiamatPublished 7 years ago 16 min read

Gangster movies never go out of style. No matter the time or era, everyone is drawn to the stories of the mafia in American cinema, whether to cringe at the horror on screen or be thrilled by the criminal underworld. The mafia and mob has offered tons of real stories about gangsters caught red handed or of men who rose the ranks only to fall – hard.

Throughout history, a few films have risen to the top. Even fewer remain relevant over the years. But the greatest ganger movies say more about life than just who got wacked and what got robbed – they speak to the human experience that we as a civilization all experience.

Nothing little about this film. One of the original emperors of the greatest gangster movies, Little Caesar tells the story of a small-time crook named Rico (the star-making role of Edward G. Robinson), and how, after moving to Chicago, he makes his fortune as a criminal, only to fall tragically.

While not the first crime film, it is one of the first gangster films. As it came out before the Hayes Code, the film got away with a lot of depictions of violence that would later be outlawed by the Hayes Code. It depicted crime in a brutal, bleak manner. While nothing here reaches Martin Scorsese levels of brutality (not even close), it was, for its day, one of the most violent films of the talkie era. (Though, of course, this is in part because the Hayes Code would shortly prevent film makers until the 50s from filming violence of any kind.)

But the biggest thing to slip through the cracks of censorship? Many critics argue that the main character of the film is actually homosexual. That was far too taboo for the time. A man who kills people for a living? A life of crime? That's fine... but a gay man? Oh, think of the children!

Named after the Biblical city and sister city of Sodom, Gomorrah is a gangster film from 2008. Most gangster films deal with the Italian mafia in some manner... but how many of the greatest gangster movies feature the gritty criminal underworld of Italy itself as seen by Italy?

Oh, and Martin Scorsese brought it over stateside so we could see it. Yet another reason why Scorsese is the king of gangster films, but... well, we'll get to him later.

This Italian film tells the story of the Casalesi Clan – a criminal organization thriving in Naples. It tells the story of five separate people, and how their lives are irrevocably destroyed by crime.

We as movie goers are so used to gangster films and crime films taking place in America about Italian-Americans that it takes us by surprise to find a film featuring crime in other countries. This makes it a contender for a unique film... but what elevates this gangster film to one of the greatest is how it shows the devastation that crime can leave on otherwise good people.

Sometimes we need a kick in the ass to remember that crime doesn't pay.

So crime doesn't pay... unless it does.

For Quentin Tarantino, his sophomoric effort proved to be one of his greatest films ever. For its time, everyone who would watch this gangster movie about the mafia, criminals, and terrible gun control skills thought it was a shoe-in for Best Picture at the Oscars. (Though most people today think that the less-crime focused Shawshank Redemptiondeserved it, and Forrest Gump ultimately was deemed the greatest film that year by the Academy. 1994 was one great year for film.)

Pulp Fiction may be a gangster film, but it isn't a Martin Scorsese or Francis Ford Coppola gangster film about the family or any of that. No, it's about cool gangsters one-upping one another, full of amazing quotes and a suitcase that everyone is after... despite the fact that the audience literally has no idea what that glowing thing is (popular theory claims the suitcase contains crime boss Marsellus Wallace's soul).

With a title like Sexy Beast, you may expect this to be a film like Boogie Nights – about pornography, exploitation. You wouldn't expect an Oscar Nominated British film about crime, would you? And you sure wouldn't expect Ben Kingsley to be a supporting actor in it, either.

Sexy Beast is a tightly told gangster film about a retired con, brought in for a big score. Our "hero," Gal, isn't really up for it... but, upon shooting the messenger, ends up feeling he has to go ahead with the score to make-up for his crimes.

While the film isn't necessarily a complex crime romp, it is effective at what it tries to do. Though Kingsley's supporting role as Don Logan is easily the highlight. He isn't starring in his film, but he may as well be, as every second he's not on screen, you miss him. It's actually funny seeing such a class-act start spouting out a hundred F-bombs in a second. Oh, and rest assured... this film is brutal.

Starring Johnny Depp and Al Pacino, this gangster film about an undercover cop in a den of crime earned Oscar Nominations and consideration of multiple AFI's Greatest Movies Ever lists. But what is it that makes this film work so well?

In many gangster films, the police are either a background obstacle or nonexistent. If they appear at all, the cops are crooked and in on whatever heist or hit is going on. Donnie Brasco, however, blurs the line between straightforward crime film and gangster movie. Johnny Depp plays an informant who becomes close with Al Pacino's assassin character. We know Depp is the "good guy"... right? I mean, he's a cop.

But, as we watch the film unfold, we realize that things aren't as straightforward as we at first believed. This makes the film enjoyable both as a straightforward gangster movie about criminals doing bad things, but also a tragic examination on how crime changes a person, even if the person is there as an essentially "good" person. Like a police officer. Because being a part of law enforcement never makes you do illicit things... right? And on that note, being a criminal means you're bad and immoral... right?

While people can ask these sorts of questions whenever only the greatest gangster movies really force us to confront these issues head-on.

American Gangster may be Ridley Scott's attempt at making a Scorsese gangster film. If you were to put this next to Goodfellas or Casino, you may be forgiven for thinking the same man was responsible for each of them. But it seems to pay off. Despite the very real people this film was based on hating the film and suing the studio, American Gangster made a ton of money and earned many awards.

Starring Denzel Washington as the newly crowned head of a Harlem crime family, we see a pursuit between two men, we watch as Denzel is chased by a Newark detective (played by Russell Crowe) in pursuit of drugs and racketeering. The rivalry between these two men leads to a years long confrontation with both the Harlem gangster families and the corrupt politicians that let them flock.

The film truly is a story of good vs evil. There are corrupt politicians and corrupt criminals. While Crowe plays the good cop, Washington really steals the show. While he commits heinous crimes, he ultimately is driven by a love for his family, and, as his crimes result in the destruction of his loved ones, we see the toll crime takes on a person.

Scott had a bit of a rough time making films in the first decade of the 21st century. This is just the sort of success he needed.

Many people make gangster movies, but no one is Martin Scorsese. Regarded as one of the greatest film directors of all time, Scorsese's vast body of work is often overshadowed by his gangster films, mainly because of how great all of them are. Of all his crime films, though, Gangs of New York is his most epic and grand.

Starring Leonardo DiCaprio as a young boy in the early days of New York. DiCaprio's father was slaughtered in a gang fight by the blood-thirsty criminal Bill the Butcher (played by the incredible Daniel Day-Lewis). Years later, he's out for revenge in the crime-ridden world of New York City.

This film is an incredibly complicated story about the old days of New York, but is also a story about the immigrant experience, how the original gangster families – the Irish Mafia – formed in part as a means of survival. It romanticizes the old way of life without shying away from its more brutal, vicious side. It's nostalgic, but also modern in its violent sensibilities. Just because it isn't Scorsese's best crime film, you should never discount that it's definitely one of the greatest crime films of all time.

Another Martin Scorsese gangster movie, many critics dismissed Casino as a longer, more over-done remake of Scorsese's most famous gangster movie (Goodfellas). It had a similar script, similar idea – hell, it even starred two of the same actors (Robert De Niro and Joe Pesci) as Scorsese's Goodfellas.

Still, over time, critics realized that Casino deserves praise as a great crime movie in and of itself.

Starring Robert De Niro as Ace, a Jewish-American mob associate put in charge of the Las Vegas Casinos, we take a decades long voyage throughout time to uncover what led to Ace becoming the victim of a car bombing. Turns out, a life of crime, a scheming wife, and a psychotic partner may have something to do with it all.

This is easily one of Scorsese's most violent films and one of the greatest gangster movies. Until the release of The Wolf of Wall Street, it possessed the highest quantity of F-bombs in a single film. But, at the same time, the film portrays the gangster life style in both a disturbing and tragic light, where characters die in underwhelming, sometimes abrupt manners that leave viewers feeling... maybe a little hollow after all is said and done.

Quentin Tarantino's debut film, Reservoir Dogs remains one of the greatest crime films ever made. Stylistic, slick, and unrelenting, the film inspired countless filmmakers that followed, and established Tarantino as a rival to Scorsese's title as the best gangster film director working in the 90s.

The film's plot is simple. A heist goes wrong. One man is bleeding out. The gang is holed up in a warehouse with the cops coming and no one to trust. Someone ratted them out... but who? They don't even know each other's names. How can they trust one another?

Pulp Fiction ultimately served as a companion film to Reservoir Dogs, which compelled fans of the former to watch Tarantino's first film. For some fans, they like Reservoir Dogs even more, in part due to its claustrophobic setting, cold mercilessness, tense premise, and, possibly most of all, its unique style.

Oh, and there's that ear thing, too. That's... that's pretty messed up. Say what you will about the bat scene in Casino – there's something so sick about dancing around like that, cutting off a guy's ear. Just grim and... kinda funny, in a sick sort of way? Is it wrong to say that?

A tragic story of betrayal and crime, Carlito's Way is a cult-classic gangster movie by Brian De Palma, the same film director behind Carrie, Scarface, and The Untouchables. While arguably not Brian De Palma's greatest film – and certainly not his most successful financially or critically – Carlito's Way has rightfully earned a cult following and loyal fanbase for its grim, tragic narrative.

Starring Al Pacino, fresh off his Oscar win for Scent of a Woman, as Carlito, the gangster film opens with Carlito leaving prison early with a fresh new chance at life... only for his friend (played by Sean Penn) to drag him back into a life of crime. As he tries to escape the life of crime he thought he had left behind, things unravel. Carlito's hopes for salvation start to trickle away as betrayal and intrigue ruins his life.

What makes this film such a success is, in part, its style. This film is action-packed, thrilling, and, all the while, very tragic. It's a sad film about the gangster life – in particular, a man who just wants to be free of it all. All filmed by one of the masters of gangster movies, Brian De Palma.

The final film by Italian film director Sergio Leone, Once Upon a Time in America is often regarded as one of his greatest movies ever. Severely edited and cut down for America, many critics regard the extended four-hour cut of the film (created as both a labor of love and through the efforts of Martin Scorsese) to be one of the greatest gangster movies of all time.

Spanning over the course of time between 1920 a 1968, the film stars Robert DeNiro and James Woods, among a cast of others that includes Burt Young, Joe Pesci, and William Forsythe, as well as younger actors playing the same roles as children. The film is... complicated. It truly is hard to recount the plot in any meaningful way, given that the film is over four hours in length.

But the intent of the film is more important than its contents. While the film does depict crime and gangster life, it is more about the American experience. The life of an immigrant, of characters suffering in the light of an indifferent, cold world. Sergio Leone may not have lived to see his film's legacy, yet, despite failing upon release, it has found an audience of cinephiles everywhere.

After starring in some of the greatest movies of all time (often with Martin Scorsese directing), Robert De Niro finally stepped up to the plate to direct and star in his own film. A Bronx Tale is a unique film about the mafia and gangster life. While many of the greatest gangster movies focus on mob bosses and assassins, this one focuses... on a boy.

The film depicts De Niro as a father who watches his son be influenced by a notorious crime lord who, despite his criminal background, truly cares for the boy's needs. The film depicts the influence these two men have on a young, developing boy, as they essentially war over whose side the child will take when he becomes a man.

A touching coming of age story with a lot of heart and humor, the film is an oddly heart-warming mafia film. While there is a lot of crime and a lot of tension, it really is unique. It truly is a "tale" of one boy's growth as a person, and of a father coming to understand that his child is growing up to be his own man. It truly is a great crime film where the crime aspect is a background detail rather than at the forefront.

Martin Scorsese's most recent gangster film (though The Wolf of Wall Street is, in essence, a gangster movie like Goodfellas without the gangsters) remains one of his best. Taking the undercover cop angle taken in Donnie Brasco, and dialing it up to 11, this epic is a story of double-agents, with a criminal infiltrating the police department while an officer infiltrates a mafia family, run by the always twisted Jack Nicolson.

The film wouldn't work without Leonardo DiCaprio and Matt Damon, who, in this film, look uncomfortably similar to one another. You really do feel a sense of disorientation trying to follow what's happening – as twists and turns happen one after another, sometimes in a brutal, intense fashion.

Beyond just being a great gangster movie, it is one of the greatest movies made. It earned its four Academy Award Wins, including Best Picture of the Year.

Of course, the only downside about this film is that it is so good that the original film, Internal Affairs, is often overshadowed. However, the Hong Kong original film, which features the triad rather than the Italian mafia, did spawn a series of sequels. The Departed doesn't have two or three sequels, does it?

But don't laugh. Some amazing gangster films have sequels. Possibly the greatest one has two.

Full disclosure: The Godfather Part I and II are my favorite movies. Not just gangster movies. Not just crime movies. Movies. Like, ever. The original film ranks consistently in the Top 3 of AFI's Greatest Movies Ever list. The Godfather Part II is one of the only sequels to ever win Best Picture at the Oscars. The third one – well, it exists, I guess.

Francis Ford Coppola's trilogy of films, based on the classic novel by Mario Puzo (who would also later write the script for Superman The Movie and its sequel), focus on the rise and fall of the Corleone crime family, from its humble origins in New York to its heights at top of the world. Throughout the films, we follow Vito Corleone (played in two Oscar winning performances by Marlon Brando and Robert De Niro), rise up from the slums, earning a loving family who adores and respects him... only for his son Michael (played by Al Pacino) to bring the family to "greater heights" at the cost of his family.

The film is a story of the immigrant experience, a tragic rise and fall story, an operatic story where EVERY character has a role... which makes us wonder if The Godfather was based on a true story. Few films have ever reached the level of epic intensity that this film reaches, and even fewer gangster movies make you forget that you're watching criminals... until it does in Part II. Brutally. It is a decades-spanning epic with an epilogue film that feels honestly... tacked on.

Part III is often maligned and hated, and it isn't very good. It's certainly a disappointment compared to the first two films. But the biggest issue is it feels unnecessary. It doesn't really add anything meaningful to the narrative that had not already been said in the first two parts. So the film trilogy has two perfect entries with a third that's sort of... who cares?

Take that third one away, and you have arguably the greatest gangster movies ever made.

...but some people would argue that there's one better film out there.

Martin Scorsese has made a lot of great films. Arguably, this is his greatest film.

Scorsese's true-crime story draws heavily from real life. Starring Ray Liotta, Robert De Niro, and Joe Pesci, this film cemented Scorsese as a great director, reshaped the crime film genre, and, on top of all else, is really damn good.

The film follows Ray Liotta's character Henry Hill from the 1950s to the 80s in a decade spanning career in the mob. The gangster life leads Henry from the criminal underbelly to prison to a whole mass of dangers. He lives the high life... only to learn that a life of crime will only lead to misery and horror.

The film has style. It has intensity. It has some of the most beautiful scenes you'd ever hope to see in a movie. But, on top of all that, it has all of that in a dense, tightly packed package. A lot of gangster movies can go a little on the long side. Once Upon a Time in America went on for four hours. The Godfather Trilogy takes place over the course of three films. But this? Two hours. Complete. Perfect.

Scorsese made a lot of great gangster movies. But to make a film that rivals The Godfather in terms of quality? It's the sort of legacy any film maker wishes they could leave.


About the Creator

Bethany Tiamat

I love three things: books with yellowed pages, long walks on beaches with my german shepard Dany, and dishes incorporating fried onions.

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