On the show, Reilly, 61, talked about how he had been enlisted by director Paul Thomas Anderson to personally recruit DiCaprio, 51, for Boogie Nights, Anderson’s boundary-pushing drama following a young man’s rise to fame in the adult film industry.
“Give me the assignment, Paul. I’ll get this guy to do your movie. I have known him since he’s a kid,” Reilly recalled telling Anderson, 55.
There was one significant obstacle: DiCaprio had already been offered the role of Jack Dawson in Titanic. Undeterred, Reilly made his argument in person.
“Listen. Leo, let me tell you something. That movie, Titanic, is about a boat that sinks. Everyone knows the boat sinks!” he recounted on the podcast. “No one’s gonna give a s**t about who’s on the boat.”
Reilly pressed further, telling DiCaprio that Anderson “is gonna be one of the most talented film directors going forward” and that he “should not miss this opportunity” to work with him.
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The Revenant star, 50, wasn’t immediately swayed. During the chat, DiCaprio’s agents were already pushing him toward Titanic, insisting it was “gonna be a really big movie,” Reilly said.
As history confirmed, they weren’t wrong. James Cameron‘s 1997 epic shattered box-office records, becoming the first film to surpass $1 billion worldwide, earned 11 Academy Awards and turned DiCaprio into one of the most recognized stars on the planet.
Yet the role’s stratospheric success came with complicated feelings. In an August 2025 Esquire interview, the Oscar winner described passing on Boogie Nights as his “biggest regret.”
DiCaprio ultimately got his chance to collaborate with Anderson on One Battle After Another. “That was very satisfying for me,” Reilly told Danson of the eventual partnership.