DiCaprio could not take it. He had already committed to James Cameron’s “Titanic,” in which he would play Jack Dawson opposite Kate Winslet.
That decision did not exactly derail his career. “Titanic” became the film that transformed DiCaprio from an acclaimed young actor into a global star.
But according to the account DiCaprio and Anderson discussed, the actor did leave his would-be director with a useful suggestion: he recommended his “Basketball Diaries” co-star Mark Wahlberg for the part instead.
Wahlberg ultimately played Dirk Diggler in the 1997 film, alongside an ensemble that included Julianne Moore, Burt Reynolds and John C. Reilly. DiCaprio, for his part, has apparently spent the intervening decades admiring the movie he did not make.
“It’s ironic that you’re the person asking that question [about regrets], but it’s true,” he told Anderson.
There are worse career mistakes than choosing “Titanic,” admittedly. Regret becomes considerably easier to live with when the alternative decision still results in one of the defining films of the 1990s.
‘One Battle After Another’ finally brings DiCaprio and Anderson together
The missed “Boogie Nights” opportunity gives their new collaboration an extra bit of history.
In “One Battle After Another,” DiCaprio plays Bob Ferguson, a washed-up revolutionary forced into action as he tries to save his teenage daughter, Willa, played by Chase Infiniti.
During their Esquire conversation, Anderson asked the obvious question: “Why did it take us so long?”
DiCaprio said the desire to work with the filmmaker had existed for roughly two decades.
“I know ‘One Battle After Another’ has been on your desk for a long time,” he said. “It was a personal story for you in a lot of ways and certainly pertinent to the world that we’re living in right now.”
For DiCaprio, however, the decision ultimately came down to both Anderson and the character.
“But ultimately, wanting to do this movie was pretty simple: I’ve been wanting to work with you—Paul—for something like twenty years now, and I loved this idea of the washed-up revolutionary trying to erase his past and disappear and try and live some sort of normal life raising his daughter.”
The film therefore arrives not simply as another prestige collaboration in DiCaprio’s increasingly selective career, but as the conclusion to one of Hollywood’s longer-running almost-partnerships.
Why ‘The Aviator’ is the DiCaprio film he actually rewatches
Anderson also turned the conversation toward DiCaprio’s existing filmography, asking whether he watches his own movies.
The answer was largely no.
“I rarely watch any of my films, but if I’m being honest, there’s one that I have watched more than others. It’s ‘The Aviator,’” DiCaprio said. “That’s simply because it was such a special moment to me.”
The 2004 Howard Hughes biopic was DiCaprio’s second film with Martin Scorsese after “Gangs of New York.” His performance as the aviation pioneer and businessman earned him an Academy Award nomination for best actor.
DiCaprio explained that his attachment to the project went beyond the performance itself. He had been carrying around a book about Hughes for years and had initially considered making the film with director Michael Mann before that version fell apart because of a scheduling conflict.
He eventually took the project to Scorsese.
“I was thirty. It was the first time as an actor I got to feel implicitly part of the production, rather than just an actor hired to play a role,” DiCaprio said. “I felt responsible in a whole new way.”
He described the film as an important point in his development from performer to creative collaborator.
“I’ve always felt proud and connected to that film as such a key part of my growing up in this industry and taking on a role of a real collaborator for the first time.”
A 30-year Hollywood near-miss finally gets its follow-up
DiCaprio’s comments make his “Boogie Nights” regret less a story about choosing the wrong film than about the collaboration that never happened.
His decision to make “Titanic” produced one of the defining roles of his career. Wahlberg’s casting, meanwhile, became inseparable from “Boogie Nights.” Even DiCaprio now says he cannot picture anyone else playing Dirk Diggler.
What remained missing was a DiCaprio-Anderson film.
“One Battle After Another” finally fills that gap when Warner Bros. releases it in cinemas on September 26. Three decades after DiCaprio declined Anderson’s first offer, the pair no longer have to discuss what their collaboration might have looked like.
They have one to watch instead.
