It sounds unthinkable now, but Chicago and Step Brothers star, John C. Reilly, once tried his best to convince Leonardo DiCaprio not to board the Titanic.
During a recent appearance on Ted Danson’s Where Everybody Knows Your Name podcast, Reilly recalled lobbying his former What’s Eating Gilbert Grape co-star to pass on James Cameron’s blockbuster in favor of another project he believed would be far more important to DiCaprio’s career: Paul Thomas Anderson’s Boogie Nights.
At the time, Anderson was assembling the cast for his 1997 drama about the rise and fall of porn star Dirk Diggler. Reilly, who had already signed on to the film, said Anderson’s first choice for the lead role was DiCaprio.
“Paul really wanted Leo DiCaprio to do it,” Reilly remembered. “I knew Leo. I met him when he was 17. I told Paul, ‘Give me the assignment. I’ll get this guy to do your movie.’”
There was just one problem. DiCaprio had also been offered the role of Jack Dawson in a little movie called Titanic.
Reilly recalled meeting with the young actor in Los Angeles and making what now ranks among Hollywood’s most famously incorrect predictions. “I said, ‘Leo, let me tell you something. That movie, Titanic, is about a boat that sinks. Everybody knows the boat sinks. No one’s going to care who’s on the boat.’”
Instead, Reilly urged DiCaprio to work with Anderson, whom he believed was destined to become one of cinema’s great filmmakers. “I told him Paul Thomas Anderson was going to be one of the most talented directors of his generation and that he shouldn’t miss the opportunity,” Reilly said.
DiCaprio ultimately ignored the advice and chose Titanic, a decision that transformed him into one of the world’s biggest movie stars. Released in 1997, the film became a global phenomenon, earning more than $2 billion worldwide and winning 11 Academy Awards.
While Reilly admitted the choice clearly worked out financially, he suggested the overwhelming fame that followed may have come with a cost. “I think the massive success that came with Titanic was both a blessing and a curse,” he said. “It was just a lot for a young man.”
DiCaprio has since acknowledged that turning down Boogie Nights remains one of the few career decisions he wishes he could revisit. In a 2025 interview with Esquire, the Oscar winner reportedly called passing on the film his “biggest regret.”
Although he missed out on Boogie Nights, DiCaprio eventually got the chance to work with Anderson decades later on the director’s 2025 action-thriller One Battle After Another.
As for Reilly, he can take comfort in one thing: predicting Titanic would sink at the box office may have been a miss, but recognizing Paul Thomas Anderson’s talent certainly wasn’t.
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