One of the defining moments of Robert De Niro’s career early on was his role as Vito Corleone in the 1974 film The Godfather Part II. De Niro won his first Academy Award for his portrayal of the young mob boss in what many consider among the best films ever made.
Vito Corleone is far from the only mobster De Niro played in his decorated career. One of his most memorable ones was David “Noodles” Aaronson in the 1984 film Once Upon a Time in America, which was legendary director Sergio Leone’s final movie.
The movie follows Noodles and his childhood friend, Max Bercovicz (played by James Woods), as they build a bootlegging empire during Prohibition. Their friendship falls apart, which eventually leads to Noodles tipping off the cops about Max’s big heist.
Years later, Noodles comes out of hiding only to realize that Max did not die from the police shootout during the heist. Noodles learns that his old friend had created a new identity and stolen his love interest, Deborah.
Once Upon a Time in America bombed at the box office. From an estimated production budget of $30 million, the film only made $5.6 million worldwide. To this day, the movie is considered one of the biggest box office flops in De Niro’s career.