American-born filmmakers have long devoted themselves to capturing the essence of our nation on film. Classics like On the Waterfront or The Last Picture Show are iconic for their honest, nuanced portrayal of a country that is as broken as it is proud. But sometimes it takes an outsider to expose the truth of a place, and no film has encapsulated the glorious, menacing tragedy of our country quite as ravishingly as Sergio Leone in Once Upon a Time in America.

A stratosphere-scraping citadel of cinema, nearly everything about Leone’s last film—and greatest masterwork—speaks to the grand illusion of the American Dream. Narratively, it is steeped in the rich, aggressively violent history of the early days of our immigrant-hating nation, depicting quite brutally the underpinnings of male-oriented corruption that render many of today’s power structures. Contextually, the film as a cultural moment speaks to the agony and ecstasy of Americana, a great movie that was infamously botched upon release in one of the most shameful studio mishaps of our time, shortly preceding the heartbreaking death of Leone—which raised many to believe that the intensity and tragedy of America itself is what brought the Italian auteur to heart failure.

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Originally a nearly six-hour epic, the 229-minute film spans an entire lifetime of Jewish immigrants-turned-mob bosses. Led by Robert De Niro and James Woods, Leone charts their rise from the Jewish ghettos of turn-of-the-century New York City to a life of lavish excess, corruption, misogyny, and betrayal as stilted grown men. Told in a kaleidoscope of unchronological fragments, the film presents the emotional passage of these two men, Noodles and Max, as they recklessly tear their way through an unmerciful society of systemic oppression and cruelty. It is smarter, superiorly affecting, more artfully shot, edited, and scored than any film of its ilk—a bonafide champion of the form, tragically overlooked in our culture.

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When the movie premiered out of competition at the Cannes Film Festival in 1984, it received a 15-minute standing ovation. But at its U.S. premiere later that year, it was discarded by critics and audiences alike, with some calling it the worst film of the year. After Leone had delivered his 229-minute cut, the American distributors at the Ladd Company shortened the film to a measly 139 minutes against the director’s will, which, according to the lore, was done by an assistant editor from Police Academy. It was an act so contentious and poorly executed that the unbelievable soundtrack by Ennio Morricone, without argument one of the best in all of cinema, was disqualified for Academy Award consideration because the producers failed to properly credit him in their new cut of the film. In fact, the film itself, after getting such exceptional praise in France, didn’t receive a single nomination here in the States at all.

It wasn’t until 2012 that American audiences got to see an approximation of Leone’s grand, nearly four-hour vision, when Martin Marin Scorsese managed to restore most of the film for a Cannes screening and DVD/Blu-Ray re-release.

What distinguishes Leone’s epic from the other great American films is its startling dedication to the portraying reality of this country.

What distinguishes Leone’s epic from the other great American films is its startling dedication to the portraying reality of this country. Unlike the sympathetic, ever-glorifying quality of mob films like Goodfellas or The Godfather (the latter of which Leone actually rejected the offer to direct in favor of this film), the gangsters in Once Upon a Time in America are just downright appalling. Whereas The Godfather construes benevolent figures like Clemenza or Marlon Brando’s puppy dog-like Don Corleone, Leone envisions mobsters for who they truly are: chauvinistic, sociopathic, emotionally splintered plagues to society.

In this way, the film becomes surprisingly prescient again today, because Once Upon a Time in America is as much a crime epic as it is an intricate exploration of entitled young men who might today call themselves incels: aggressively masculine, dismissive of women, yet violently obsessed with achieving sexual dominance.

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Fitting in to the ever-burdensome history of American cinema’s fascination with sexual violence against women, Once Upon a Time in America features a vicious rape sequence that illustrates terrifyingly the wicked dangers of this form of male behavior. While I’d never advocate for films that indulge in this sort of tired rape narrative, it feels only natural that a movie immersed in American history and culture would have such a fascination with violence against women.

Somehow, in spite of all their deplorable actions, it’s just impossible to take your eyes off the criminals of Leone’s “Kosher Nostra” film. Like the characters of all the truly great mob classics, Noodles and Max are empowered as a by product of their environment: early 20th century America. In typical Leone fashion, the film studies the faces of its cast intimately and defiantly, preferring long, extreme close-ups over action or set pieces to convey emotional depth. These close ups have become quintessential touchstones in the dictionaries of cinema, with filmmakers like Quentin Tarantino expressing publicly the deep importance of the Leone close up. But more significantly than its obsession with the faces of Robert De Niro, James Woods, William Forsythe, Elizabeth McGovern, and a staggering swath of other prominent 1980s-era stars, is Leone and cinematographer Tonino Delli Colli’s dedication to showcasing the transporting beauty, decadence, and decay of America.

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There are three eras of our nation portrayed non-linearly in the film: the hard Jewish ghettos of Manhattan’s Lower East Side in the 1920s, the Great Gatsby-esque exuberance of the 1930s Prohibition, and then the dark, gang-ridden streets of 1968 New York, post-modernity. Leone seeks to capture each era of New York with poetic truth on camera and in spirit. The early days of De Niro’s Noodles are full of childlike wonder for the Big City that so many have used as a synecdoche for our country as a whole. The wide shot of Noodles’s gang walking in Lower Manhattan with the massive Manhattan Bridge looming in the background has become iconic, with the old bridge looking almost like a hulking giant of fairy tales. Later, when De Niro’s character is released from prison, the Prohibition era of New York is portrayed almost like a playground for men of power, with rich decor, gaudy costumes, and grandiosity spilling into every frame.

And then Leone’s vision for the New York of 1968 is foreign and strange, perhaps reflective of what his view of the country may have felt like, being an aging Italian native making films in an industry that had deeply shifted from its auteristic roots, with frisbees whizzing around the city like UFOs and Rockwell-esque bar scenes amidst darkened corridors appearing almost like dreams.

The deeply mysterious ending of Once Upon a Time in America has puzzled viewers for decades. The film, which begins on an image of De Niro as a young man in 1930s New York silencing the terror of his tormented criminal life by suckling on a long pipe in an opium den, also ends with the same scene—although this time, Noodles is lying with his face up, smiling at the camera. Was it all a dream? Or perhaps a nightmare?

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One cannot help but wonder what this ending may have meant to Leone, a filmmaker who was as profoundly influential to American cinema and culture in general as he was indebted to it. His obsession with cowboys in the American west, and the lawlessness of a country that, from its earliest days, was relentless against the weak and uninitiated, may have imbued the director with this mystifying sense of narrative and moral ambiguity.

Leone died shortly after the film was released in its ruinous form by studio producers keen on presenting a more traditional movie for the multiplexes. His colleagues and collaborators have spoken at length in interviews about how the changes to Once Upon a Time in America deeply hurt the last great Italian auteur, with James Woods even going as far to say that Leone died of a broken heart. Today, in light of what the film tried to accomplish, and how it was treated upon release by a changing 1980s culture where the divide between the Raging Bulls and the Rocky IVs was ever-widening, the ending feels exceptionally haunting. Whatever the meaning, it feels only natural that a film about the American dream should end with something resembling a nightmare.

Dom Nero Video Editor Dom Nero is a staff video editor at Esquire, where he also writes about film, comedy, and video games.

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