In their heads, Leonardo DiCaprio and Paul Thomas Anderson are just a couple of cool guys in their 30s

Interviewing each other ahead of their new film One Battle After Another, DiCaprio and Anderson said they feel 32 and 27, respectively.

By William Hughes  |  August 13, 2025 | 9:28pm
Leonardo DiCaprio (Photo: Andreas Rentz/Getty Images) and Paul Thomas Anderson (Photo: Charley Gallay/Getty Images for TCM)
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In their heads, Leonardo DiCaprio and Paul Thomas Anderson are just a couple of cool guys in their 30s
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There’s a lot to recommend about the “one famous person interviews another” format that’s been making the rounds in journalistic circles of late. Yes, you get some softballs thrown into the mix, and a basic “we’re all in this together” sympathy that might preclude hard questions being asked. But it’s also pretty much the only way to get certain notably guarded stars—like, say, Leonardo DiCaprio—to go on record from within their comfort zones, as DiCaprio did in a recent Esquire interview with fellow frequent reporter-phobe Paul Thomas Anderson. The pair are currently deep into collaboration mode, currently promoting their first film together, One Battle After Another, and were pretty ready to cut loose about their careers (and occasional mocking of Esquire‘s offered list of questions).

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. (Anderson pursued DiCaprio for the part back in the ’90s, but the actor turned him down due to time commitments on Titanic, pointing Anderson toward his former co-star Mark Wahlberg instead.) The two men spend a while basically asking why they’d never managed to work together in the intervening time, despite a long-standing mutual admiration, before Anderson pivots to something way less Hollywood history, and more genuinely interesting:

Anderson: I’m going to ask you a question, and you’re going to answer as quickly as you can. If you didn’t know how old you are, how old are you right now?

DiCaprio: Thirty-two.

Which is legitimately kind of fascinating (especially after Anderson notes that his own mental age is 27, i.e., the age he was at when Boogie Nights landed in theaters). DiCaprio, meanwhile, is apparently trapped in between The Aviator—by his own account the only one of his films he still regularly watches—and The Departed.  (“What you’ll have to do is investigate what happened when you were thirty-two,” Anderson notes, “And then you’re going to discover and uncover why that was your answer.”)

And while we’re well aware that DiCaprio’s response opens up room for, roughly, 8 million jokes about his dating history, it’s also an interesting reflection on where the just-turned-50 actor is sitting mentally right now: Deep into his long-running collaboration with Martin Scorsese, and just pushing into more of a production role on his own films. It’s at least a more productive view into his worldview than the annoyed “Sheesh” he gives when Anderson gamely fires the Esquire-provided question, “You give so much to every role you play, once filming wraps, what do you do to come down from it?” which Anderson eventually reframes into something slightly more palatable to the two hip, young 30-somethings’ mental sensibilities.

One Battle After Another hits theaters on September 26.

 
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