Clint Eastwood Turned Downed This Sergio Leone Cult Classic, and He Had a Reason: "I Like to Know the Joke"

Sergio Leone and Clint Eastwood will forever be linked thanks to the legendary Dollars Trilogy. Their creative partnership seemed destined for years of fruitful collaboration, yet reality proved more complex.

Leone offered Eastwood the lead in his next two movies, Once Upon a Time in the West and Duck, You Sucker!, but the actor declined both roles.

What is less well known is that the director also wanted to cast his favorite star in the epic crime saga that ultimately became Once Upon a Time in America – yet once again, Eastwood declined.

Eastwood Refused to Collaborate With Leone on 'Once Upon a Time in America' – He Needed Something More Than an Idea

As Clint Eastwood recalled, Leone started developing the idea for a gangster movie while working on The Good, the Bad and the Ugly in the mid-1960s. At that time, the director approached the actor with a proposal:

“He said, ‘What about Irish gangsters? You could play an Irish gangster?’ Long before The Godfather and all these things came out, but he never developed it. It was always just there, hanging there.”

However, Eastwood was in no rush to agree. The project remained a vague concept for years, and Leone was notoriously unhurried about bringing it to fruition.

Ultimately, Once Upon a Time in America became his first feature film in 13 years. For Eastwood, who was accustomed to clear scripts and firm deadlines, this was unacceptable:

“As time went on, I didn't think it was a wise thing to do. With him or anyone else.”

The actor insisted on having guarantees – he wanted to know what kind of situation he was getting into, what his role would be, and, most importantly, how it would all end:

“I like to know the joke. I don't want someone to tell me a joke and not give me the punchline.”

The collaboration did not materialize because Leone couldn't provide Eastwood with a finished script or a clear resolution. The director turned to other actors instead, ultimately casting Robert De Niro in the lead role.

Ultimately, Robert De Niro Played the Lead Role – And He Did a Brilliant Job

Clint Eastwood's refusal opened the door for Robert De Niro. By that time, De Niro was already an acclaimed master thanks to his roles in The Godfather Part II and Taxi Driver, so he brought incredible depth to the character of David "Noodles" Aaronson.

He created two vastly different personas: a young, ambitious gangster and an aging, world-weary man haunted by his memories. De Niro guides viewers through an entire era, serving as a conduit into a world of betrayal, violence, and nostalgia.

Once Upon a Time in America is still one of the actor's greatest works, proving that one artist's refusal can become another's opportunity, ultimately resulting in a classic.

What Did Critics & Viewers Think of 'Once Upon a Time in America'?

• Once Upon a Time in America has 86% from critics and 93% from viewers on Rotten Tomatoes.

• On IMDb, the movie has a score of 8.3/10.

• On Letterboxd, Once Upon a Time in America scored 4.2/5.0.

Where to Watch 'Once Upon a Time in America'?

Once Upon a Time in America is available to buy or rent on Amazon Prime Video.