All 5 Gangster Movies That Won the Best Picture Oscar, Ranked

You can go back pretty far in time to find releases that support the idea of gangster movies having been pretty much always popular, to some extent. There was Dr. Mabuse, the Gambler in the silent era, which kind of laid the groundwork for the genre a little like how another Fritz Lang movie, Metropolis, laid the groundwork for sci-fi films going forward. And then by the time talkies were a thing, you had all the early gangster movies that really recognizably feel like they belong to the genre, because they’re dated in terms of content, but not really basic structure, nor narratively. There’s still a lot that can be gotten out of watching the likes of Scarface (1932), Little Caesar, The Public Enemy, and White Heat, if the last of those can include itself within that early “classic” era of gangster movies.

It took until the second half of the 20th century before movies definable as gangster ones started winning Best Picture. In fact, no crime movie won Best Picture until 1954, and that one was sort of a gangster movie. Like, there are going to be a few “sort of” picks here. If a movie concerns organized crime to a reasonable extent, or at least some of its characters can be considered gangsters, then the movie’s a gangster one, for present purposes. So, no West Side Story (1961), even if that’s about gangs (just teenage ones, not really organized the same way proper mobsters are), and no The Silence of the Lambs or No Country for Old Men, even if they’re definitely crime movies. In almost 100 years of history, five movies that either are gangster films or are sort of gangster films have won Best Picture, and all of them are ranked below.

5

‘The Sting’ (1973)

Image via Universal Pictures

Coming between the two most legendary gangster movies to have won Best Picture is The Sting, which does get a little crushed by the two winners on either side of it, but it shouldn’t be entirely smothered/overshadowed. Unless you think it’s not gangster-focused enough, in which case, you’re free to overlook it or laugh at the fact that it was included here. Admittedly, the two main characters here (played by Paul Newman and Robert Redford) are con men rather than full-on mobsters/gangsters, but they’re targeting someone who very much is wrapped up in organized crime. Said target is a very powerful mobster responsible for the death of one of their friends, and so they enact a complex scheme to effectively steal all his money, as revenge.

Call it more of a heist movie then, if you want, but even then, The Sting has a different sort of energy compared to various other heist films, and lots of that comes down to the tone, because The Sting is quite frequently a comedy on top of being a heist/crime/drama/(sort of) gangster film. And it’s all fun to watch, even if it’s a bit simple and perhaps a little laidback. But then also, maybe the laidback feel is, in the eyes of some, a benefit. It’s a cruisy kind of caper movie, and perhaps that’s enough. There’s certainly style and charm here, the latter in heavy quantities thanks to the pairing of Newman and Redford. Hope you don’t mind hearing some variations of “The Entertainer” about 511 times throughout the entire movie, though.

4

‘The Departed’ (2006)

Image via Warner Bros. Pictures

The Departed was made pretty late into Martin Scorsese’s career, all things considered, in turn being far from his first gangster movie. Mean Streets, Goodfellas, Casino, and Gangs of New York all came before, and compared to at least a couple of those, many would consider The Departed inferior. However, that’s comparing something great to things that are greater, and so what shouldn’t be taken away from, when it comes to The Departed is, you know, a degree of greatness. Also, it’s a little different as far as Scorsese gangster movies go, since there are just as many prominent characters here on the other side of the law (compared to Goodfellas, for example, when just about every main or supporting character is either in the mob, or incredibly close to/associated with it).

In The Departed, there’s an undercover cop infiltrating a criminal gang, and then one of the criminals from that gang infiltrates the police force around the same time. There, you have a reliable source of thrills and suspense, because one has to out the other while protecting his own identity all the while. The Departed makes all that exciting for pretty much its entire runtime, and even if it sometimes feels more concerned with being a thriller than a gangster film, that’s okay. For one, the thrills are indeed thrilling, and for another thing, it’s not really going for the same sort of gangster thing other Scorsese movies might. For what it’s trying to do, and for what it’s trying to be, The Departed largely excels.

3

‘On the Waterfront’ (1954)

Image via Columbia Pictures

It’s probably easier to label On the Waterfront a gangster movie than The Sting, all the while acknowledging that it’s still not one that aims to immerse you in a mobster’s life, nor is the main character a literal gangster. But, like The Sting, it is about someone whose life is affected by organized crime in various ways, and he kind of exists alongside certain gangsters before deciding to make a stand against them. Gangsters who’ve taken over the local union drive most of the conflict in On the Waterfront, so that’s the main reason it feels worth including here.

Either way, it’s a phenomenal movie, too, and it says something about how great 1954 was that On the Waterfront might only be the second-best movie of the year (Seven Samurai would have to be the first, though it wasn’t nominated for Best Picture). Also, it’s easy to point – and worth pointing – out that Marlon Brando delivered an Oscar-winning performance in this almost-gangster movie, and then, less than two decades later, he’d win his second Oscar for starring in another Best Picture winner, though that one was very easily definable as a gangster film. Speaking of…

2

‘The Godfather’ (1972)

The most usual of all the suspects, perhaps even more so than its sequel (which, yeah, is probably going to have to be #1 here, so, sorry about the spoilers), here’s The Godfather. You could be a little questioning of whether On the Waterfront deserved to be here as a full-on gangster movie, but there are no such reservations when it comes to The Godfather. This one defined what gangster movies could (or maybe even should) be for the New Hollywood era onwards, much like how the various classics from the early 1930s set the stage in terms of what could be done with the genre back then. It’s a real epic, taking place across almost a decade, being about a criminal empire that’s also run by a family: the Corleones, plus some other associates who might well be like family.

In that sense, it’s famously a family drama on top of being an epic-scale gangster movie, and so even if gangster movies might not ordinarily have appeal to everyone, there is a lot here, and so just about anyone can likely find something compelling to grab hold of. It’s also no exaggeration to say that The Godfather is one of the best-written and best-acted movies of all time, so those qualities help immensely in it being considered an absolute all-timer. There is a clear character arc for Michael here, and the story goes from being mostly about his father, Vito, to being about him by the end, but then there are so many other places for such a narrative to go further, many of them explored just two years later.

1

‘The Godfather Part II’ (1974)

Image via Paramount Pictures

Yep, two years later, here’s The Godfather Part II. Michael is the boss now, well and truly, and he realizes how progressively difficult that is as things go on. He has some similar qualities to his father, Vito, but not all that he needs, and a certain coldness is what seems to make his leadership of the Corleone crime family feel less secure than his father’s. Said father remains a part of The Godfather Part II, thanks to plenty of flashbacks to his time as a younger man, setting up what would eventually become his crime empire, and the way it’s edited, you get to see the rise and the fall of the family empire at the same time. Without the structure, it would feel derivative of the sorts of old-fashioned (yes, even old-fashioned by 1970s standards) gangster films made in the 1930s, but the scale here, and the use of time… all that’s instrumental in The Godfather Part II being as successful as it is.

If you wanted to consider it an even stronger Best Picture winner than The Godfather, then that’s honestly fair enough. Similarly, it might well have an even better screenplay, just because it’s tackling even more difficult stuff thematically while being longer and a little more adventurous with its structure, owing to the way it functions as a sequel and almost something of a prequel simultaneously. Or, to call into question this whole ranking right near the end, maybe The Godfather Part II was mentioned after The Godfather because it’s just easier to talk about them that way. Maybe they’re the same, quality-wise, and it matters very little which one’s considered “the best” and which one’s the “second best.” They are the first two Godfather movies, and little else matters.