Sergio Leone is a name that echoes through cinema history, primarily for his groundbreaking work in the spaghetti Western genre. While many cinephiles instantly think of The Good, the Bad and the Ugly—and rightly so—Leone's later years produced a trio of films that, while thematically linked, are often less discussed. This is the Once Upon a Time trilogy, a loose collection of films that showcase Leone's evolution as a storyteller, his deep love for genre, and his unparalleled visual style. But which of these three cinematic gems is the best? Let's break them down, from the most underrated to the absolute masterpiece.
The Underrated Gem: Once Upon a Time... the Revolution (1971)
Also known as Duck, You Sucker! or A Fistful of Dynamite, this film is the most misunderstood of the trilogy. The title confusion alone is a hurdle, but the movie itself is a sprawling, bleak, and surprisingly emotional epic set against the backdrop of the Mexican Revolution. It's a war film as much as a Western, and it's arguably Leone's most dramatic and challenging work. The story follows a Mexican bandit and an Irish revolutionary who form an unlikely alliance, and their journey is filled with both explosive action and profound tragedy. It's a film that rewards patience, and while it might not be as immediately accessible as its siblings, it's a deeply rewarding experience that deserves far more recognition. It's a testament to Leone's range that he could follow the operatic Once Upon a Time in the West with something this raw and politically charged.
The Epic Masterpiece: Once Upon a Time in the West (1968)
This is the film that many consider to be Leone's true magnum opus, and it's easy to see why. Once Upon a Time in the West is a slow-burn, operatic Western that trades the rapid-fire action of the Dollars trilogy for a more deliberate, almost meditative pace. The plot revolves around a mysterious harmonica-playing stranger, a ruthless railroad magnate, and a widow fighting to keep her land. It's a story about the death of the Old West, the rise of industrialization, and the personal vendettas that fuel the narrative. The opening sequence, a nearly 15-minute scene with three gunmen waiting at a train station, is a masterclass in tension and visual storytelling. The film is a visual and auditory feast, with Ennio Morricone's iconic score weaving through every frame. It's a film that demands your full attention and rewards it with one of the most emotionally resonant finales in cinema history.
The Grand Finale: Once Upon a Time in America (1984)
Leone's final film is a sprawling, 229-minute crime epic that traces the lives of Jewish gangsters in New York City from the 1920s to the 1960s. It's a film about friendship, betrayal, memory, and the American Dream, and it's as far from a Western as Leone ever got. The film is a complex, non-linear narrative that jumps between time periods, and it's anchored by a career-best performance from Robert De Niro. It's a melancholic, deeply personal film that feels like a summation of Leone's career, exploring themes of loss and the passage of time with a profound sense of regret. While it was butchered by the studio upon its initial release, the restored version is now widely considered a masterpiece, and it's a fitting swan song for a director who always aimed for the epic.
So, which is the best? It's a tough call, but Once Upon a Time in the West edges out the competition. It's the perfect synthesis of Leone's style—the sweeping visuals, the iconic score, the mythic storytelling—and it's a film that has influenced countless directors since. It's not just a great Western; it's a great film, period. But the other two are essential viewing for any serious film fan. If you're looking for a starting point, Once Upon a Time in the West is the most accessible, but don't sleep on the other two. They're all worth your time, and they all showcase why Sergio Leone remains a titan of cinema.
For more cinematic rankings, check out our list of classic sci-fi films or our take on Spider-Man villains. And if you're in the mood for something more modern, we've also ranked flawless action movies since 2010.
