The 8 Most Ambitious Gangster Movies of All Time, Ranked
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There have been some epic gangster movies released throughout cinema history, especially within the last 50 or so years. The accomplishments of earlier efforts (like The Public Enemy, Little Caesar, and The Roaring Twenties) shouldn’t be overlooked, but once you move past that golden/classic era of gangster movies, from around the 1930s, you do find a bunch that are ultimately longer, and definitely more ambitious in scope.
The ones below are arguably the most ambitious gangster movies ever made. It’s not the same thing as ranking the absolute greatest gangster films of all time, because some of the very best aren’t specifically mentioned below, but if you want gangster movies done on an epic scale, offering something unique, and, more often than not, having long runtimes, then that’s what you're going to find below.
8 'Casino' (1995)
Martin Scorsese is inevitably going to be mentioned when you're talking about gangster movies, but what might be surprising is not including Goodfellas here. It is absolutely one of the best gangster films ever, but the focus here is more on gangster films that feel ambitious and like true epics, and while Goodfellas is juggling a lot all at once, it’s a bit too personal, small-scale, and short to be a true epic (but its runtime of 140-ish minutes is still decently beefy, sure).
With Casino, it’s a bit like a bigger Goodfellas. With it having some similarities, that does maybe make it a little less ambitious in terms of content and style, but it does go bigger, it runs for longer, it builds a world to a greater extent (you do feel like you get a sense of how the entirety of Las Vegas operates), and it does push boundaries in terms of how dark and violent it’s willing to get, even by the standards of the gangster genre. It being one of the most intense and sprawling gangster films of all time is enough to make it worthy of inclusion here.
7 'Scarface' (1983)
Scarface is cool for a few reasons, but maybe the coolest thing it does is be a remake while still feeling tremendously original and ambitious. Sure, the basic story here is the one you can find in the Scarface that was made 50 years earlier, and it’s a familiar story when it comes to gangster films generally speaking, too, since Scarface (either version) is about a criminal experiencing a dramatic rise in power, wealth, and influence, and then a more dramatic fall from grace.
Scarface is maximalist, and it also functions as an epic, compared to the leaner gangster movies of old, Scarface (1932) included.
1983’s Scarface is maximalist, and it also functions as an epic, compared to the leaner gangster movies of old, Scarface (1932) included. This 1983 version runs for almost three hours and is a perhaps unintentional perfect snapshot of the 1980s, made in the decade itself, capturing the style and music most associated with that period… whether it’s accurate, eh, you'd have to ask someone older. But it captures that heightened ‘80s vibe well, and it’s also hard to resist a movie that feels so big while also managing to be so very entertaining.
6 'Pulp Fiction' (1994)
It’s mostly the way that Pulp Fiction is written and edited that makes it feel ambitious, if you're willing to count it as a gangster movie in the first place, of course. There are a few different storylines here, told in an unusual way (and out of order), but they all come back to – and revolve around – a gangster named Marsellus Wallace, even though he’s not really the main character.
Also, perhaps unexpectedly, there is a good deal of comedy here, and some initially controversial violence, even if later films directed by Quentin Tarantino ended up being a whole lot more bloodthirsty. It’s got a great flow, even though it should be choppy and messy, and then the ending is also an all-time great one, even if that ending scene is far from the last one to occur chronologically. How Pulp Fiction holds together, all the while working as well as it does… who the hell knows?
5 'Gangs of New York' (2002)
There isn't a ton of love for Gangs of New York, compared to some other Martin Scorsese gangster movies, but it’s better than you’ve likely heard. Further, it’s worthy of consideration here, since it’s hugely ambitious on a technical front. It’s hard to overlook Gangs of New York if you're into production value and the overall look/feel of the film, since all that’s immense.
Further, the story is broad and sweeping, there are quite a few characters to keep track of throughout, and it does quite a lot with its narrative focused on revenge. Beyond that, though, Scorsese also feels like he wants to explore the violent history of the city he so often explores and depicts throughout his filmography, and he uses a historical setting/time period to look at the character of the city overall, with some relevance to the present day (mostly seen in that ending… but the ending isn't the only masterful scene here, since the opening sequence of Gangs of New York is also phenomenal, and unlike anything else in Scorsese’s filmography).
4 'The Irishman' (2019)
Like a good many crime/gangster movies out there, The Irishman stars Robert De Niro, and the narrative involves a man who lived a violent and crime-filled life looking back on it… which makes it similar to another film, that one from 1984, which will be mentioned shortly. There are narrative and emotional similarities between the two epics, but stylistically, both are quite different. And, on a technical front, there’s also the fact that The Irishman stars older actors who have to act younger, while in the other film, De Niro and most of the other cast members were younger (or middle-aged), and then some had to act older in certain scenes.
The important thing is that The Irishman is a crime epic, and it’s hugely ambitious with its use of special effects and what it’s going for technically, even if it stumbles a little with such technology, because making actors in their 70s look 30 to 40 years younger is still a big ask. But it’s probably even more effective as a devastating character drama, and an unflinching look at aging, mortality, and regret, with those aspects still hitting hard. It’s technically not perfect, but what The Irishman accomplishes and gets right is pretty staggering, and it’s the kind of film where it feels likely that time will be kind to it.
3 'The Godfather Part II' (1974)
An honorable mention should go out to The Godfather, without a doubt, but it’s The Godfather Part II that feels like more of an epic, and it’s therefore arguably more ambitious. You could go further and say it’s better as a movie overall, too, but that’s another argument for another time. What matters here is ambition, and The Godfather Part II is longer, narratively/thematically riskier, and it does some interesting things with its structure and editing, too.
While the first movie was heavy-going at times for sure, The Godfather Part II dials all that up considerably, or maybe it’s more accurate to say it dials things down, because you'll probably be feeling down yourself by the time that it wraps up. Technically, things wrap up in The Godfather Part III, but that one’s not essential, and the ending of The Godfather Part II is stronger in any event (all the while also being perhaps the greatest accomplishment of Francis Ford Coppola’s entire directing career).
2 'Gangs of Wasseypur' (2012)
It’s got a similar title to Gangs of New York, but Gangs of Wasseypur is considerably more epic in scope, mostly thanks to it being two movies in one, essentially. Both volumes were released in the same year, and they add up to make one huge epic, a little like how Kill Bill: The Whole Bloody Affair is one movie, even though it was originally released in two volumes. Maybe it’d be easier to compare Gangs of Wasseypur to The Godfather and The Godfather Part II, because it has a similar scope to those films, but is itself one film (again, more or less).
The main difference is that Gangs of Wasseypur is mostly told in chronological order, but the important thing is you still get a decades-spanning conflict and more than one generation looked at, with its focus on a crime family and all. Taking it as one massive epic, it’s overall very suspenseful, unpredictable, exciting, and unapologetically violent, well and truly feeling ambitious enough to go toe-to-toe with some of the other (more well-known) classic gangster films from cinema history.
1 'Once Upon a Time in America' (1984)
Once Upon a Time in America spans many decades, with a focus on characters as kids, and then later as adults. When they're younger, they begin engaging in certain criminal activities and find the life somewhat intoxicating, and then by adulthood, they're full-on gangsters, ensuring the film feels like a proper gangster movie, with that part of the film concerning the whole Prohibition era, when people wrapped up in organized crime were able to get wealthy by selling then-illegal liquor.
The ambition comes about because of the non-chronological storytelling of the whole thing, though, a little like Pulp Fiction, but the different timelines here are years (or even decades) apart, rather than the days or maybe weeks that separate the different threads in Pulp Fiction. Further, Once Upon a Time in America is bold and uncompromising when it comes to looking at how ruthless and destructive gangsters can be, further unpacking what happens to an immoral individual as they get older, and deconstructing the whole genre in the process. There’s a lot going on, to put it mildly, so the epic runtime is utilized very well, and it’s absolutely one of Sergio Leone’s finest achievements as a filmmaker.
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