The Top 10 Gangster Films of All Time

By Terris Ko · November 10, 2014

Editor’s Introduction: They are the hard-boiled bruisers we love, and love to hate. All the usual suspects are here (well, except that movie, sorry): De Niro, Pesci, Pacino, Depp, Sinatra, etc. These tough guys steal the screen when it comes to hard laughs and hard drinks, but they stop pulses when it comes time to “get down to business.” Without further adieu, here are the ten best gangster films to be put to screen.

10. Casino (1995)

Martin Scorsese paints a surprisingly human portrait of gangsters in Casino, showing how fragile the individuals actually can be; gangsters might be fearsome with a gun in hand and when surrounded by their gang mates, but there were lonely, confused people behind (at least some of) those gruff exteriors. Robert De Niro, for one, as a gambling savant whose life becomes uncontrollably complicated when he falls for Sharon Stone’s femme fatale. Joe Pesci, for another, a manchild with a temperament to match, who can’t seem to get out of his own way.

If you wanted to learn about the casino business, the walkthrough sequence in Casino isn’t a bad place to start.

Of note: De Niro and Joe Pesci, like a couple of kindred spirits karmically bound at the hip, are reincarnated as a duo in Casino for the third time, this time with a little less love for each other.

8. Guys and Dolls (1955)

Gangsters were never nicer or funnier (until Analyze This (1999))–or more likely to break out into song–than they were in Guys and Dolls.

Marlon Brando and Frank Sinatra team up, not as tough guys (per se), but as song and dance men who are in over their heads–especially when it comes to love. Is there any group of gangsters in movie history that audiences root for to find a happily ever after?

7. Donnie Brasco (1997)

Another glimpse at the life of a gangster, but this time from the point of view of the drone instead of the alpha male (think Star Wars from the POV of a stormtrooper). Watching the same actor who played arguably the most iconic don in film history turn around and play a schleppy low level worker bee is like looking through the looking glass, like an imagining of what Michael Corleone’s life might have been if he weren’t born to one of the most powerful crime families in New York City; and Al Pacino disappears into the role: we see that life for his middle-aged gangster isn’t full of silk suits and sit-downs.

To boot, Brasco is based on a true story, and offers a glimpse into the life of an undercover agent, buried so deeply that he came to know the wiseguys intimately, even becoming close friends with Pacino’s sad-sack gangster, which is part of our takeaway: at the end of the day, they’re regular people, too.

Also: Johnny Depp playing just a normal guy. When was the last time we saw that?

6. Scarface (1983)

The American dream writ large, a rags to riches tale wrapped inside an Aesop’s Fable. This is what might have happened if the kids from the Brazilian slums in City of God made their way across the sea to the United States.

Using the ironic “World Is Yours” exclamation point from Jimmy Cagney’s version of Scarface as the springboard, director Brian DePalma explores the shiny version of the American Dream, where cash, fast cars and women are all that anyone wants.

The lesson: the higher you go, the lonelier it gets. All that’s left in the end is Scarface and “his little friend.”

5. Reservoir Dogs (1992)

Dovetail structure: check. Machine-gun fire dialogue: check. A cast of quirky, unforgettable characters: check. Reservoir Dogs was Quentin Tarentino’s lean directorial debut, where so much of the inciting action happens off-screen, and the drama unfolds in the aftermath as a handful of gangsters who had never met before this heist-gone-wrong they were hired to work on try to piece together what the hell just happened.

Proof that you don’t have to go big or go home. Just make sure you do your work with story and character.

4. The Untouchables (1987)

What happens when the good guys are straightlaced, play-by-the-book types going after the biggest kingpin of them all? There’s a steep (but thrilling) learning curve. Few films pack in so many memorable action sequences (the raid at the Canadian border, the shootout at the train station (Brian DePalma’s homage to the Odessa Steps sequence in Battleship Potemkin), the rooftop confrontation while a trial is going on downstairs) without letting the set pieces become a distraction to the story.

Kevin Costner in his first notable turn as leading man, the return of Sean Connery (in an Oscar-winning role), and the introduction of Andy Garcia. And of course, Robert De Niro as Al Capone.

Also of note is the Oscar-nominated score by legend Ennio Morricone.

Three word summary: Death and Taxes.

3. City of God (2002)

A peek into the desperation that possibly drives people to a life of crime; after all, when you’re so low on the totem pole that there’s no place to go but up, what’s left to lose?

City of God is pure kinetic cinema, documenting the poverty and privation of slum life–not to mention the brutality and disregard for any human life that stood in the way of what the gangsters wanted–at a dizzying pace and in an unfolding structure that almost puts Tarentino to shame.

2. Goodfellas (1990)

The glamorized veneer of the lifestyle that mesmerized so many in The Godfather is stripped away as Scorsese gives gangster-worshippers some tough love lessons in the real world–or, realer world, vis a vis The Godfather–of gangsters.

Martin Scorsese recognizes the appeal of the gangster-life; our narrator Henry Hill (our eyes into the world) recounts how kids from the neighborhood carried his mother’s groceries home. “It was outta respect.” But we soon learn through Henry’s experience that that respect was like one of the drugs that Hill ended up dealing; addictive, with fleeting effects and too often, not worth the price of admission.

1. The Godfather (1972) and The Godfather: Part II (1974)

What can be said about The Godfather films that hasn’t already been said? The films belong at the top of the list if for no reason than for how they’re firmly entrenched in the collective consciousness of anyone who’s seen them.

But ultimately, The Godfather is a cautionary tale reminding us that while the American Dream is attainable, be careful how you go about achieving that dream, as certain paths come with a price to pay–if not now, then somewhere down the line. Maybe the film’s greatest feat: making us sympathize with the bad guys, as if they were the victims, people simply chasing down a chance at a better life and waylaid by the badder-bad guys.

Where The Godfather plays in part like a love letter to strength of family, The Godfather: Part II is a Greek Tragedy, the vanquishing hero of the first part broken by the ongoing burden of a responsibility he never wanted to bear, becoming the very thing he had always dreaded.

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