Skip to main content
Close

Top 10 Best Gangster Films

By Riley Webster · May 15, 2013

I dunno what it is, exactly, about gangster films being so enjoyable… but they are.  Maybe they help us release our inner violent demons, maybe it's because we all secretly enjoy seeing two people in nice suits yell profanities at each other, or maybe it's just that great gangster films can bring out the best in writers, directors, and actors….I don't know.

What I do know is that these 10 films belong not only on a list of great gangster flicks, but a list of great films, period.  Despite their sometimes numbing violence and narcissism, these are inherently very entertaining movies, every last one of them, and I hope you agree.

Of course, there are the admissions.  Many flicks that several other people consider "gangster" films, I would put in another category — films like Heat, French Connection, and L.A. Confidential would be more "cop" movies, for me, and I wasn't quite sure what to classify Bonnie & Clyde

And here are the ones I do consider gangster films, but sadly, these came up just a little bit short: Reservoir Dogs, Miller's Crossing, Road to Perdition, The Untouchables, Lock Stock and Two Smoking Barrels, Snatch, Carlito's Way, Public Enemies, Mean Streets, Scarface (1932), and Little Caesar. I know, some of you will hate me for snubbing the above mentioned, but there is only room for the Top 10, and so it goes….

10. White Heat (1949)

I'm slightly ashamed to say that my knowledge of classic, 1930-1940's gangster pictures is slim, and that White Heat is the only James Cagney film I've seen.  But what an introduction to his work — his portrayal of Cody Jetter is up there with Jack Nicholson's The Joker for perfectly snarling movie villains.  Cody is a horrible person, but a wonderful movie gangster, equipped with all the necessary (and now clichéd) traits; the inimitable voice, the penchant for shooting everyone who gets in his way, his casual mistreatment of his wife, and his gloriously bloody demise.

For a film made in 1949, White Heat is surprisingly modern — the first 25 minutes are almost one long action sequence, moving from an exciting train heist to a riveting car chase.  Most movies back in the 40's established their characters and scenario's in quite a slow, methodical manner, but White Heat jumps right in, guns blazing.  The second act of the film is more of a prison break movie, and the third a violent and epic heist picture, complete with a cat-and-mouse sub-plot not unlike The Departed.

I loved White Heat.  The Oscar nominated screenplay is very good, and the direction and supporting actors all do fine.  But the real star is James Cagney, probably the most famous gangster-actor who ever lived, and he's just deliciously evil in the film.  Don't make the mistake of thinking just because it's old, it's dated — there is barely anything about the movie that doesn't still play well today.

9. Dick Tracy (1990)

I guess more than any other film I pick on this list, Dick Tracy will be the one that sticks out the most.  It's been undervalued, under-seen, and under-appreciated it's entire life, and after complaining in the introduction about movies like Heat and Bonnie & Clyde that I wasn't sure counted as true "gangster" films, I bet a lot of people reading this will be confused by Dick Tracy's placement.  But here's the thing — what do you think of when I say "gangster film"?  Me, I think of larger-than-life villains, shoot-outs with tommy guns, period cars and costumes, lots of cigarettes and femme fatale's, and an exciting story filled with murder, corruption, and deception.

Well, Dick Tracy has all that in spades, as well as possibly remaining the most original, inventive, and true-to-the-original comic book adaptation ever made.  The colours literally splash out at the viewer; Warren Beatty, who starred as Tracy and also directed, only used the brightest prime colours on the visual palette, so that the film truly took on the form of a comic strip come to life.  It's a brilliant cinematic technique, but what is often overlooked is how visually brilliant the cinematography is aside from the colour scheme (the director of photography was the great Vittorio Storaro).

Dick Tracy is just about as much fun as I can have watching a movie.  It's a parade of famous actors hamming it up as much as possible, from Al Pacino to Dustin Hoffman to Dick Van Dyke (!!!!)  The story is a revolving door of endless baddie gangsters trying to off the great detective in yellow, but it's more cleverly written than it gets credit for, and the twist at the end was actually very surprising upon its release.  Now that the film has been re-released on Blu-Ray, I hope everyone can check out Dick Tracy, which is not only an underrated gangster film, but a great film period.

8. Scarface (1983)

I don't know if there's ever been a movie more excessive than Scarface.  I'm not just talking about the excess shown by the characters within their own world (the level of crime, bad language, 80's suits, 80's nightclubs, and 80's cocaine-mountains are astonishing).  But also, "excess" in terms of the filmmakers themselves — Oliver Stone has never again written a film so over-the-top (which is saying a lot) and Brian de Palma has never again directed a film with so much visual flair and fluidity (also saying a lot).  And hell, Al Pacino has never before, or since, gone so ridiculously crazy on camera.

Scarface is a typical rags-to-riches-to-death-in-a-fountain story, where Al Pacino plays Tony Montana, a Cuban gangster who immigrates to Florida and becomes one of the country's more dangerous, wealthy, and powerful crime lords.  All of the subtlety and panache that Pacino had in his portrayal of Michael Corelone in the Godfather saga is thrown out the window here — Tony Montana sneers, snarls, and chews his way through every bit of scenery he can find.  It's delightful to watch.

As I mentioned, both the script and direction are ludicrous, but in a good way, and the costumes, set design, and music are so incredibly 80's that there are times the film becomes a black comedy.  But despite these dated or slightly humourous things, Scarface is still an epic gangster film with a dark morality tale in its center (the last part being obviously lost on everyone who seems to think Tony is some kind of hero…trust me, he isn't).

7. The Departed (2006)

Expect to see a lot of Martin Scorsese on this list — gangster films are to him what fruits and veggies are to body builders.  I almost didn't put this one on the list, though, thinking it might count more as a "cop" movie, like French Connection and Heat, than a gangster picture.  But then I thought about the moments that most stick out, and the character I most remember, and it all came down to the lead gangster, played through a haze of psychotic embellishment by Jack Nicholson.  And I realized any film with this gangster as its lead villain has to count in this genre.   He's too deliciously nasty to ignore.

The Departed doesn't contain just one great character though — it gives us several, from Leo DiCaprio's tortured cop-playing-gangster, to Matt Damon's gangster-playing-cop, to Mark Wahlberg's inexplicably Oscar nominated role as a rude police detective.  William Monaghan's script (which actually won the Oscar, alongside Scorsese's long-delayed award) is filled with juicy lines and bizarrely clever sequences, filled with tension, action, blood, and humour. 

The Departed is an absolute blast to watch; for all of its 150 minute running time, it's never remotely boring or stagnant, and Scorsese directs with just as much flair as he did when he was half his age.  The soundtrack/score combination works perfectly as well… it's just one of those movies were everything clicked, and we were the ones that got to reap the rewards. 

6. Casino (1995)

Call it the sequel to Goodfellas that no one really wanted, but it is almost impossible not to love and admire.  Martin Scorsese's almost-immediate follow-up to his 1990 gangster epic took some hits at the time for being almost too similar to Goodfellas — the two lead actors are the same, the co-screen-writer is the same, the excessively awesome visual and aural style that only Scorsese can achieve is very much the same.  But Casino tells a very different story; one that is more epic, more nuanced, more tragic.  Despite not being as fun or daring as Goodfellas, Casino is in many ways an equally strong film.

Casino follows Ace Rothman (Robert De Niro), a gangster bookie who gets to run a casino in Vegas, with the help (or not-help) of gangster buddy Nicky Santaro (Joe Pesci, of course).  The movie is very long and episodic, as are most of Scorsese's films (especially when dealing with a true-life story that really did expand over the course of many years).  But, like Goodfellas, the movie is infused with so much excitement and boundless joy that it's rare that I actually feel the 3+ hours go by. 

The movie is more graphically violent than Goodfellas (a corn-field murder is one of the more disturbing scenes of recent cinema) and I believe it still holds the record for most f-words ever used in a film (apparently 2 per minute — go, Joe Pesci!!!)  But it's a valuable story worth telling, and it's shown in the most interesting and entertaining way imaginable.  Combine that with brilliant performances (not just De Niro and Pesci, but Sharon Stone is even pretty good at playing a despicable witch) and a great soundtrack, and Casino is easily in the top 10 gangster films ever.

5. City of God (2003)

Sadly the only foreign language film on my list, Fernando Merrielles' brilliant debut film City of God deserves comparison with the famous likes of Pulp Fiction and The Godfather.  Like Scorsese's best films, City of God is an exuberant and visually stylish movie that pumps you up within minutes of watching.  I recently taught foreign film to a class of grade 8 students, and the opening of this movie was one of the first I showed — the rapid-fire cutting, the shaky camera-work, the blasting music, the harsh lightings… these are all things that frequently seem cheesy or over-used, but here are as natural as the shabby houses the gangsters live in.

Unlike, say, Casino, City of God does not ever really show the upside of gangster life.  The slums of Rio de Janeiro are not Las Vegas, and these people turning to a life of embittered and violent crime do so not out of joy or desire for riches, but out of pure necessity and survival.  Indeed, one of the most powerful sub-plots is how a generally decent man is not only corrupted by gang life, but winds up being one of the city's most forceful and violent residents. 

But the plot doesn't matter much.  Despite it also zipping across different time-lines and consistently defying expectations, this movie is exciting and deliriously demented because of the direction, editing, and cinematography.  It may not make you want to take a trip to Rio de Janeiro any time soon, but as an expose of grungy, poverty-stricken gang life, it's illuminating.

4. Pulp Fiction (1994)

My excessive infatuation with Pulp Fiction was short-lived — when I saw it in eleventh grade, I thought it was the most brilliant thing ever and Quentin Tarantino was a genius, and then I watched Jackie Brown, Kill Bill's, and Death Proof, and decided only the first part of that statement is true.  Tarantino is a massive egotistical blowhard, and just about every one of his films since Pulp have been over-praised.  But the thing is… if everyone called me Jesus, I wouldn't believe them, but if I performed a miracle like Pulp Fiction, I kinda would.  It truly is a terrific movie, and one of the best (and most audacious) screenplays ever written.

Pulp Fiction famously contains several different time-and-story-lines, criss-crossing all over the place.  What should've been confusing and abstract was relatively easy to follow, and became a huge worldwide phenomenon, influencing filmmakers for decades to come (for better or for worse).  The movie was controversial upon release with its sudden graphic violence and penchant for profanity-laced dialogue, but both of those things are so common place now, they hardly seem earth-shattering anymore (indeed, if you watch the violent scenes closely, you'll be surprised how restrained it is, especially compared to Tarantino's Django Unchained).

No, the real brilliance from Pulp comes from an epic story construction, hilariously dark pop-infused dialogue, and a small world of wonderful characters like the gangsters played by John Travolta and Samuel L. Jackson.  Yes, the movie is quoted more times than Casablanca, and you can barely see any college dorm-room without a picture of the two leads aiming their guns and spouting Biblical nonsense.  But strip away the praise and fame, and at it's heart Pulp Fiction is still just a flat-out awesome screenplay.

3. The Godfather Part 2 (1974)

There seems to be two kinds of people in the world — those that love the first Godfather the most, and those that prefer the second (I guess there's probably people who like the third installment most, but… that would be a mighty small gathering of folks).  For me personally, the first Godfather is the one that sings the loudest; the second installment rambles a bit more, and the flashback structure of showing how Vito Corleone got his start (played excellently by Robert De Niro) has a bad habit of taking me out of the suspense of the main story.  But having said all this, Godfather 2 is still one of the greatest of all films, and combines the drama of a Greek tragedy with the excitement of a hard-hitting gangster epic.

The film moves back and forth between the aforementioned flashback sequences and the main story, following Michael Corleone has he tries to uncover the traitor in his family.  This main plot, containing possibly Al Pacino's best and most calculated performance, is of the real interest here; as with any "prequel", there is less tension with the flashbacks, because we already know what's going to happen.  But the scenes involving Michael stand out in the memory as strongly as anything in the first — the attack on his home, the trip to Cuba, the round-about way he lies to everyone, and the shocking admission by his wife about their baby.  When I mentioned "Greek tragedy", I meant it.

The two Godfather films together are probably the best representation of the "Gangster Dream" as you can possibly get — if Goodfellas is the harsh reality, than the Godfather's are the romantic ideals, the thought of what could have been, if only we hadn't screwed it all up.  The second installment is longer and less violent, but still has the power to captivate and enthrall.

2. Goodfellas (1990)

Has there ever been a more passionate and exuberant film than Goodfellas?  More specifically, has there ever been a director who so clearly loved such brutal and unforgiveable characters?  That sense of love is a key to why Goodfellas works so much — this is the film Martin Scorsese wanted to make as a kid, back when he saw the power these gangsters wielded in the streets of New York, and desperately wanted to join their club.  Most kids have those kind of fantasies at some point, and luckily most of them grow out of it, realizing that a decadent world of drugs, sex, crime, and violence has it's (lethal) detriments.  But Goodfellas is a film almost leaping out of the screen with excitement.

If you ever get to watch the DVD/Blu-Ray, check out the special feature that simply shows a dozen famous filmmakers talking about how much they love the film.  People like Frank Darabont even say that "every Sunday while making Shawshank, I watched Goodfellas".  It's an inspiring example of great flimmaking; the cut's are rapid and choppy, the camera frenetic and constantly in motion, the dialogue laced with dark black humour and a million f-words.  Despite containing great performances from Robert De Niro, Ray Liotta, and especially Joe Pesci as a horrifying psychopath, the real star of the film is Martin Scorsese — every frame is imbued with his touch, and makes it a blast to watch.

The details are impeccable; despite the fact that the rather plot-less film rambles across 3 decades of Mafia life, you never get the sense that you're not in that exact moment in time, whether it's the cars, the clothes, or the attitudes.  The more I watch Goofellas, the more I realize how impossible it must've seemed, to make a movie about these kind of people so inherently enjoyable, while also retaining it's capacity to frighten and disturb.  It's just a helluva film.

1. The Godfather (1972)

It's nearly impossible to find someone's list of top 10 films without the inclusion of Francis Ford Coppola's sprawling gangster saga.  But unlike, say, Citizen Kane, Godfather's stature doesn't come from being the most cinematically innovative or influential film — rather, it's considered so highly because it simply tells an amazing story, and does it almost perfectly.  Coppola adapted the lengthy and intricate Mario Puzo novel with great panache, allowing the characters room to breathe, and enveloping us completely in the world of this Mafia family.

For those 5 of you that haven't yet seen The Godfather, the movie follows two main characters — the older Don of the Corleone crime family (famously played by Marlon Brando) and his son Michael, who goes from classy poster boy to violent sociopath when asked to take control of the business (played by Al Pacino in an understated but wonderful performance).  The movie is long, yes, but it never feels long — rather, I could be totally happy with another 3 hours added to the run time of this flick.  And the movie is violent, but in a classy, subtle way, compared to the blood-and-guts bonanza's of today.

The Godfather is so often called a perfect, great, classic movie, it may almost seem anti-climactic to include it at the top of this list….but it deserves all the praise it receives.  There's barely anything I would change about it (except, of course, the James Caan fight scene, which is embarrassingly bad).  The fact that Coppola achieved one of cinema's best films under the strain he did; constant studio interference, almost being fired, unhappy actors, etc, is nothing short of a miracle.  The Godfather may not show the dark underbelly of gangster life as viscerally as Goodfellas, but as an epic and wonderful cinematic achievement, it's rarely been equaled by any movie, of any genre.