Leonardo DiCaprio Tells Paul Thomas Anderson His Biggest Career Regret: Not Doing Boogie Nights
Sep 16, 2025
Leonardo DiCaprio had a pretty good 1997: He starred in Titanic, one of the most successful movies ever made. But in a new interview he tells Paul Thomas Anderson, his director in the upcoming One Battle After Another, that he wishes he’d made another movie that came out in 1997, Anderson’s Boogie Nights.
DiCaprio and Anderson spoke at length for an Esquire piece in which the director and actor recorded two separate conversation, which the magazine then condensed and edited. Anderson’s first question for DiCaprio was simple: “Any regrets?”
DiCaprio told Anderson that he wished he’d starred in his film Boogie Nights, in which Mark Wahlberg ultimately starred as Dirk Diggler, a young man who has a rapid rise and disastrous descent in the adult entertainment industry of 1970s and ’80s.
“I’ll say it even though you’re here: My biggest regret is not doing Boogie Nights,” DiCaprio said in the Esquire interview, which you can read in full here. “It was a profound movie of my generation. I can’t imagine anyone but Mark in it. When I finally got to see that movie, I just thought it was a masterpiece. It’s ironic that you’re the person asking that question, but it’s true.”
DiCaprio had starred with Wahlberg in 1995’s The Basketball Diaries, and they also both starred in Martin Scorsese’s 2007 Best Picture winner The Departed.
In the Esquire interview, DiCaprio and Anderson didn’t go into detail about why DiCaprio didn’t do Boogie Nights, but it likely that the exhausting shooting schedule for Titanic may have been a factor. It wasn’t the worst decision: The James Cameron film was a massive hit and won 11 Oscars, including for Best Picture.
Twenty-eight years after Boogie Nights, DiCaprio and Anderson are finally working together for the first time in One Battle After Another, in which DiCaprio plays a middle-aged leftist revolutionary trying to stay ahead of the law while dealing with a rebellious daughter (Chase Infiniti).
As Anderson explains in the Esquire piece, he borrowed aspects of the Thomas Pynchon novel Vineland — “I stole the parts that spoke to me and just started running like a thief,” he explains.
Paul Thomas Anderson and Leonardo DiCaprio on Rewatching Old Films
Leonardo DiCaprio in One Battle After Another, directed by Paul Thomas Anderson. Warner Bros.
Anderson asked DiCaprio if he ever watches his own films, and DiCaprio says he rarely does — but that he watches Scorsese’s 2005 Howard Hughes biopic The Aviator “more than the others.”
“That’s simply because it was such a special moment to me. I had worked with Marty on Gangs of New York, and I’d been toting around a book on Howard Hughes for 10 years. I almost did it with Michael Mann, but there was a conflict and I ended up bringing it to Marty. I was 30. 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. I felt responsible in a whole new way.” 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.”
They also discussed their mutual love for 1998’s Midnight Run, starring Charles Grodin as a mob accountant and Robert DeNiro as a bounty hunter who has to shepherd him across the country.
I saw it three or four times the week it came out. It’s the high-water mark of a great film for a broad audience, Anderson said, calling Midnight Run “the total package.”
“When my dad was telling me about what acting is, he took me to the theater in Burbank to watch Midnight Run. He said: ‘You want to be an actor, son? That’s the guy right there—that’s acting,’” DiCaprio added.
One Battle After Another arrives in theaters September 26, from Warner Bros.
Main image: Leonardo DiCaprio in Titanic, Twentieth Century Fox/Mark Wahlberg in Boogie Nights, New Line Cinema
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