The most interesting stuff, from a historical counterfactuals point of view, pops up early, when Anderson opens by asking DiCaprio if he has any big regrets, and immediately gets back “not doing Boogie Nights ” in response.

Leonardo DiCaprio opened up to Paul Thomas Anderson for 'Esquire' about turning 50 and feeling 'emotionally' in his 30s.

Leonardo DiCaprio turned 50 last year, but mentally he’s decades younger. The Oscar-winning actor opened up about his emotional age in a rare interview for Esquire, where he was interviewed by director Paul Thomas Anderson. The two collaborated together for the first time in their upcoming film, “One Battle After Another.”

According to the report, Paul Thomas Anderson wanted to cast DiCaprio in 1997 film Boogie Nights after watching his performance in The Basketball Diaries

For those unaware, Caprio's mother, Irmelin Indenbirken, has worked as a legal secretary. The Titanic actor was asked by Anderson to "answer as quickly," if you "didn't know how old you are, how old are you right now?" Leonardo DiCaprio replied that he is 32 years old.

Leonardo DiCaprio fights many battles in the trailer for Paul Thomas Anderson ‘s latest film, One Battle After Another. DiCaprio shared the film’s trailer to his own brand-new YouTube channel ...

For his recent Esquire cover shoot, Leonardo DiCaprio wore a Rolex Oyster Perpetual 41 in pistachio green – reference 134300 – one of the standout releases of 2025.

He starred in Titanic, one of the most successful movies ever made. But The post Leonardo DiCaprio Tells Paul Thomas Anderson His ‘Biggest Regret’: Not Doing Boogie Nights appeared first on MovieMaker Magazine.