De Niro recommended DiCaprio to Scorsese after this forgotten 1990s movie
De Niro apparently passed the torch as Scorsese's leading man.

Do we have Robert De Niro to thank for pairing Martin Scorsese with Leonardo DiCaprio? Did Scorsese's original, iconic leading man of Taxi Driver, Raging Bull, Goodfellas and more make it possible for DiCaprio to star in Gangs of New York, The Departed and The Wolf of Street? That's probably oversimplifying things, but according to Scorsese himself it's not far from the truth, as De Niro told the director about the young DiCaprio after working with him on a relatively overlooked movie from the 1990s.
Promoting his new movie, Killers of the Flower Moon, which stars both De Niro and DiCaprio, Scorsese sat down with GQ to discuss many of his iconic movies. After discussing Taxi Driver, which was De Niro's first leading role with Scorsese (he was supporting to Harvey Keitel in Mean Streets), Scorsese talks about Gangs of New York, his first movie with DiCaprio.
"He [De Niro] called me and said at one point, he just made a film called This Boy's Life and he was working with this kid that he cast named Leo DiCaprio," Scorsese recalled. "He said, 'he's very good, you've got to work with him someday.' And Bob never really used to tell me that, 'work with somebody.'"
Scorsese added that Gangs of New York had been a project he wanted to do many times but had been cancelled for one reason or another. But off of De Niro’s suggestion, he met with DiCaprio about the movie. As they say, the rest is history.
But what is This Boy's Life?
Based on literary professor Tobias Wolff's memoir about growing up in the 1950s with his abusive stepfather, This Boy's Life sees DiCaprio play the young Toby and De Niro plays his stepfather, Dwight. The cast was rounded out with Ellen Barkin, Chris Cooper, Eliza Dushku, Carla Gugino and Tobey Maguire, while the movie was directed by Michael Caton-Jones (Memphis Belle, The Jackal).
This Boy's Life opened on April 9, 1993. While Rotten Tomatoes has it with pretty solid reviews (a "Fresh" 76% from critics and an 80% positive from audiences), the movie did very little at the box office, bringing in $4.1 million. The biggest takeaway from the movie was DiCaprio, who earned multiple nominations and a couple of wins from the Chicago and Los Angeles Film Critics Associations for his performance. However, those laudits were always shared with DiCaprio's other movie of 1993, What's Eating Gilbert Grape?
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Gilbert Grape definitely overshadows DiCaprio's work on This Boy's Life in the pop culture discussion, as he was nominated for his first Oscar for Gilbert Grape. But, if De Niro's recommendation of DiCaprio to Scorsese is being directly attributed to their team co-starring in This Boy's Life, then that movie helped land DiCaprio two more Oscar nominations for The Aviator and The Wolf of Wall Street, both of which he did with Scorsese.
All in all, including the upcoming Killers of the Flower Moon, DiCaprio has starred in six Martin Scorsese movies, including Scorsese's lone Best Picture winner to date, The Departed. Though DiCaprio still trails De Niro, who has now starred in 10 Scorsese movies.
Bringing it full circle, Killers of the Flower Moon is the first feature length movie that De Niro and DiCaprio have starred in together since This Boy's Life and their first feature length Scorsese movie together. That distinction is necessary because they did do a short, The Audition, which was directed by none other than Scorsese to promote a hotel casino resort in Asia.
You can watch The Audition short film on YouTube right now, while This Boy's Life is currently available via digital on-demand platforms. Killers of the Flower Moon, meanwhile, premieres exclusively in movie theaters worldwide on October 20 before heading to Apple TV Plus at an as yet undetermined date.

Michael Balderston is What to Watch’s assistant managing editor and lead movie writer, covering movies coming to theaters, writing movie reviews and highlighting new and classic movies on streaming services; he also covers a range of TV shows, including those in the Taylor Sheridan universe, Slow Horses, Only Murders in the Building, Jeopardy!, Saturday Night Live and more, as well as the best ways to watch some major US sporting events.
Based outside of Washington, D.C., Michael's previous experience includes writing for Awards Circuit, TV Technology and The Wrap.
Michael’s favorite movie of all time is Casablanca, while his favorite TV show is Seinfeld. Some 2025 favorites include One of Them Days and Black Bag for movies, and The Pitt on TV. Follow on Letterboxd to keep up with what I'm watching.