Sergio Leone is primarily known for directing some of the greatest spaghetti westerns ever made, from the Dollars trilogy to Once Upon a Time in the West, but on the back end of his career, he came to the U.S. to give the crime genre a go. He turned out Once Upon a Time in America, one of the finest gangster epics ever put on film, starring Robert De Niro and James Woods.

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Leone’s cut was butchered by the distributors, but his original version has since been released and is regarded as a cinematic classic. A movie of this size always has some fascinating behind-the-scenes details.

Sergio Leone First Became Interested In The Story In 1967

A wide shot of New York in Sergio Leone's Once Upon a Time in America

Sergio Leone first read The Hoods and became interested in adapting it in 1967, just after he’d finished The Good, the Bad, and the Ugly. However, the movie wouldn’t come out for another 17 years. During that time, he directed two other movies and produced a bunch of others.

Throughout this time, the script went through several drafts and Leone continuously met with author Harry Grey to understand his perspective on America. Leone passed on helming The Godfather because he was committed to getting this movie made.

Norman Mailer Wrote A Rejected Draft Of The Script

Norman Mailer

Norman Mailer was interested in collaborating with Sergio Leone, so the director let him take a crack at the script for Once Upon a Time in America. Mailer holed up in a hotel room in Rome with some whiskey bottles, a few boxes of Cuban cigars, and a typewriter. Three weeks later, he’d churned out a draft of the script, then met with Harry Grey to nail it down.

However, Leone found this script to be unusable, and aside from that, Mailer’s vision for the story was at odds with his own, so he rejected it. Mailer was furious and sued Leone and the Ladd Company for an undisclosed settlement.

John Milius Was Sergio Leone’s First Choice To Direct

Robert Duvall on a battlefield in Apocalypse Now

In the early stages of development, Sergio Leone didn’t plan to direct Once Upon a Time in America himself. His top choice was John Milius. Despite being a fan of Leone’s, Milius was too busy making The Wind and the Lion and writing Apocalypse Now to commit to the project.

Leone also met with Miloš Forman, but he eventually decided to make Ragtime instead. So, Leone ended up sitting in the director’s chair himself.

Leone Met With More Than 3,000 Actors For The Movie

The young cast of Once Upon a Time in America standing in old style costumes

Between 1980 and 1982, Sergio Leone was committedly wholeheartedly to pre-production on Once Upon a Time in America, dividing his time between scouting for locations, overseeing script rewrites, and meeting with over 3,000 actors for the film’s more than 100 speaking roles.

Al Pacino And Jack Nicholson Both Turned Down The Lead Role

Al Pacino in The Godfather

Both Al Pacino and Jack Nicholson turned down the lead role of Noodles before Robert De Niro was cast. De Niro was the first actor cast in Once Upon a Time in America, having been approached for the part while he was shooting The Godfather Part II, and once he was on board, he became heavily involved in casting the other roles.

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Regular Leone collaborator Clint Eastwood was reportedly offered the role of Jimmy O’Donnell, but turned it down. The role of Max was offered to John Belushi, but he passed away before the audition process began.

Joe Pesci Was Cast As A Favor To Robert De Niro

Joe Pesci in Once Upon a Time in America

Joe Pesci auditioned to play Max, but Sergio Leone didn’t think he was right for the part. As a favor to his star Robert De Niro, a close friend of Pesci’s, Leone allowed Pesci to pick any role he wanted from the remainder of the uncast roles.

Pesci chose Frankie, whose role was much bigger in the script than it ended up being in the final movie, since hours of material got cut out.

Nobody On The Crew Spoke Any English

Once Upon a Time in America

According to Scott Tiler, the actor who played Noodles’ younger self, nobody on the crew could speak any English. Even director Sergio Leone only ever used one English word on the set: “Goodbye.”

Ennio Morricone’s Score Was Played On The Set During Filming

Robert De Niro and James Woods in Once Upon a Time in America

Since Once Upon a Time in America took so long to get made, Ennio Morricone had finished composing the score before filming was even halfway complete.

In order to create a suitable atmosphere for the film, Leone played pieces from Morricone’s score on the set during filming.

Sergio Leone Wanted To Release The Movie In Two Parts, Each Three Hours Long

Robert De Niro in Once Upon a Time in America

At the end of production, the footage in Once Upon a Time in America ran over eight hours, which no movie theater would play for obvious reasons. Sergio Leone and his editor Nino Baragli managed to cut the movie down to six hours.

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Leone’s plan was to split this six-hour opus in half and release it in two three-hour parts, but the producers refused, so the director further trimmed it down to three hours and 49 minutes.

Hollywood Executives Infamously Chopped Down Leone’s Cut

Noodles and Max in Once Upon a Time in America

After cutting down Once Upon a Time in America to a 269-minute beast that he was happy with, the producers necessitated Leone to trim it down even more, so he got it down to 229 minutes for its Cannes premiere.

However, the U.S. distributors still thought it was way too long, so they gutted the movie and cut it down to a virtually incomprehensible 139 minutes, against Leone’s wishes.

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