Every Movie in Sergio Leone's Once Upon a Time Trilogy, Ranked
Jeremy has more than 2700 published articles on Collider to his name, and has been writing for the site since February 2022. He's an omnivore when it comes to his movie-watching diet, so will gladly watch and write about almost anything, from old Godzilla films to gangster flicks to samurai movies to classic musicals to the French New Wave to the MCU... well, maybe not the Disney+ shows.
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The Sergio Leone movie you're probably most likely to have seen is The Good, the Bad and the Ugly. That one might well be the best, or at least you can understand why it’s the most iconic. The Sergio Leone movie you're second most likely to have seen… uh, that’s a bit harder to guess. It’s something that isn't The Colossus of Rhodes, which was his directorial debut. That movie came out in 1961, and it’s kind of understandable why few people know about it. It’s not very good, and Sergio Leone’s style doesn’t really shine through. It took until the Dollars trilogy for him to become recognized as a director, with the aforementioned The Good, the Bad and the Ugly being the final movie in that trilogy, even if it’s possible that it takes place before A Fistful of Dollars and For a Few Dollars More chronologically.
Those movies didn’t make Sergio Leone legendary in his time, because spaghetti Westerns weren’t always taken seriously, and it feels like more people have come to recognize how good they are in the years since. Sergio Leone directed another loose trilogy after the Dollars films, and these ones also weren’t fully appreciated to the extent they should’ve been. Like, the Academy Awards aren’t everything, even when they get more things right, but none of Leone’s movies ever got a single Oscar nomination, which is kind of absurd, frankly, just for how they look and sound alone (Ennio Morricone’s scores are always a highlight). The second Leone trilogy has been more appreciated as time has gone on, too. It’s admittedly more of a thematic trilogy than the already loose Dollars trilogy, but the films share a “Once Upon a Time” motif in their titles, so that’s how they're linked, and that’s why they're being ranked. Well, one movie only kind of has “Once Upon a Time” in one of its titles. It’s complicated. Speaking of complications…
3 'Once Upon a Time... the Revolution,' AKA 'Duck, You Sucker!' (1971)
This is the complicated movie, when it comes to titles. It’s hard to know what to call this movie, which is the second of the Once Upon a Time trilogy, but isn't often referred to by its “Once Upon a Time” title. The best title would be Once Upon a Time... the Revolution, though, because that links it with the other two movies, and it also sounds the best. Like, the most popular title is probably Duck, You Sucker!, which is the worst of the bunch. You'll also sometimes see this movie called A Fistful of Dynamite, which is a tiny bit better, but still not as good as Once Upon a Time... the Revolution. A Fistful of Dynamite just feels like an attempt to link it to A Fistful of Dollars, and that’s misleading, because this is a considerably longer, bleaker, and more challenging Western than A Fistful of Dollars. Actually, it’s bleaker and more challenging than all the Westerns Leone directed (the genre for which he’s best known, since his only non-Westerns were The Colossus of Rhodes and his final film… but more on that final film a little further down).
Once Upon a Time... the Revolution is one of the most underrated movies of its era, or maybe even of all time.
Anyway, it’s Once Upon a Time... the Revolution. That’s the best title. Using it here might well help further the idea that it should be called that, over the other titles. Once Upon a Time... the Revolution is one of the most underrated movies of its era, or maybe even of all time, and it’s fantastic, to the point where having to rank it last here hurts. But it’s the kind of film that might get, like, an A-, if you were grading it, while the other two Once Upon a Time movies are both well and truly A-grade, or possibly even worthy of an A+. Once Upon a Time... the Revolution does indeed play out against the backdrop of the 1910s Mexican Revolution, only just scraping by into the period of time that most Westerns take place in. It functions as a war movie at the same time, and then it’s also intensely tragic at points, being maybe the most drama-heavy of any Sergio Leone film. It’s offbeat and potentially not for everyone, but it’s got a lot to offer, and it’s extremely well-made, all the while having an admirably unique tone, too.
2 'Once Upon a Time in the West' (1968)
Unambiguously called Once Upon a Time in the West, this one is the first in the Once Upon a Time trilogy, and it’s pretty much a coin flip between this and the other movie, if you're trying to determine the best of the bunch. Once Upon a Time in the West is also the Sergio Leone Western that you might well find people placing above The Good, the Bad and the Ugly, and it’s hard to be envious of the people making such a decision, because it’s very hard to pick a favorite of the two. Leone just knew how to make a Western, and Once Upon a Time in the West is perfect while being very different tonally and pacing-wise from the also pretty much perfect The Good, the Bad and the Ugly. There are four main characters here, and the plot mostly involves a bloody dispute over a piece of land that’s highly desirable. That’s simplifying things a bit. Once Upon a Time in the West isn't really too narrative-focused.
What it does dramatically is still interesting, and there is eventually a ton of emotion here, once certain things come to light in the film’s final act. Once Upon a Time in the West does draw things out before then, miraculously without ever feeling boring. That’s especially apparent in the long opening scene, which has a trio of people waiting at a remote train station for another person to arrive. That’s it. You're watching people wait, and Leone makes it entertaining. The same goes for a good many other sequences that can’t really be called set pieces, because they're not particularly explosive or action-packed, but they're riveting in unexpected ways. The whole movie is kind of like that, and it’s hard to put into words just what works so well about Once Upon a Time in the West. You also can only go so far in trying to rave about how good this film looks and sounds, too. Everyone brought their A-game, and it really does feel like Sergio Leone’s ambitious vision for the whole epic was well and truly realized.
1 'Once Upon a Time in America' (1984)
Once Upon a Time in America shook things up, as an entry in Sergio Leone’s filmography, by being his sole gangster movie, and also being the only one based on a book. It’s not super accurate to say it’s the only Sergio Leone movie based on a pre-existing story, since A Fistful of Dollars was rather infamously an unofficial remake of Yojimbo, but yeah, still not a book. The source material here, a novel called The Hoods, by Harry Grey, is fairly obscure. And it was published in 1952, while Once Upon a Time in America spans decades and ends up in the 1960s, so it’s not a direct adaptation or anything. To keep the focus on the film, it doesn’t really start in the 1910s and end in the 1960s, because it’s told in a non-chronological way… but the earliest events in the movie take place during the former decade, and the final events (chronologically speaking) of the movie take place in the latter decade.
So, to call Once Upon a Time in America an epic would be an understatement, because it’s about a long stretch of time, and then it’s also about four hours long, too. Or it’s a bit longer, if you watch the most complete cut. It’s only the severely cut-down original U.S. cut that has to be avoided, because it was chopped down to 139 minutes, and the storytelling was made chronological. It ruined the film, or that’s what the people who saw that cut say, and you have to go by their opinions because that’s not a widely available cut nowadays. Once Upon a Time in America probably stood the best chance of being properly appreciated in its time, since it was clearly a labor of love, and epic gangster movies had done well in the previous decade, what with The Godfather and its sequel coming out then and all. Honestly, Once Upon a Time in America is about at their level, quality-wise. It’s a more brutal and despairing gangster movie than even The Godfather Part II, and goes to some incredibly dark places, but with reason, and it’s powerfully done as a stark look at crime and a group of genuinely irredeemable gangsters. On a technical front, it matches how impressive Leone’s previous several movies had been, too. It’s unfortunate that Once Upon a Time in America ended up being a swansong, since it was Sergio Leone’s final film, and he wasn’t old when he passed away in 1929 (at 60 years of age). Still, what a legacy he ultimately left behind, and the three Once Upon a Time movies are all essential in strengthening said cinematic legacy.
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