The two first met when DiCaprio auditioned for the 1993 drama 'This Boy's Life'
De Niro, 80, was already a two-time Oscar winner when he went to work on the 1993 movie This Boy’s Life, a coming of age story set in the 1950s and based on Tobias Wolff’s 1989 memoir of the same name.
DiCaprio, 49, who then was best known for his role on the ABC sitcom Growing Pains, came in to read for a role, but not the lead part of Tobias that he eventually landed.
“I said to Art Linson, the producer, I said, ‘Art, that kid was really, it was interesting.’ I didn't push it. I just said, ‘That kid had something special,’ and then they turned around and wound up using Leo,” De Niro says in the new issue of PEOPLE.
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In the film, DiCaprio plays the 15-year-old Tobias, whose single mother Caroline (Ellen Barkin) whisks them away to Washington state and gets involved with Dwight Hansen (De Niro), a man who offers the family some stability.
After Caroline marries him, his more sinister side comes into focus: he’s mean and verbally abusive, and he focuses his ire on the young Toby, humiliating him and demeaning him at every turn.
Three years after This Boy’s Life was released, De Niro and DiCaprio both appeared in the 1996 drama Marvin’s Room with Diane Keaton and Meryl Streep.
Their third and latest film, Killers of the Flower Moon, tells the heartbreaking true story of the Osage Reign of Terror. In 1920s Oklahoma, a seemingly-benevolent White man named William Hale (De Niro) orchestrates the murders of many Indigenous people in order to steal their land, which is rich with oil deposits.
DiCaprio plays Hale’s simple-minded nephew Ernest, who marries Mollie (Lily Gladstone) an Osage woman. Hale, of course, has Mollie in his crosshairs.
Asked where Hale ranks on the spectrum of all the bad guys he’s played in his career, De Niro says he’s up there.
“He’s pretty bad. But again, it's what's called the banality of evil, and the way I interpret that is that…these evil things that he does, he doesn't think are evil. So it's one of the most insidious, I guess, characters,” he says.
“[He’s] a pillar of the community, and then doing these other underhanded things,” he continues. “It's baffling to me because I don't understand it.”
De Niro’s latest nod is his eighth acting Oscar nomination (he has one more for producing Best Picture nominee The Irishman), putting him in elite company with just 17 performers in all of Hollywood history who have eight or more acting nominations.
Killers of the Flower Moon is now streaming on Apple TV+.
For more on Robert De Niro, pick up the new issue of PEOPLE.
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Read the original article on People.