Leonardo DiCaprio Says Turning Down ‘Boogie Nights’ Is His Biggest Career Regret: “It Was a Masterpiece”

Leonardo DiCaprio has one big “what if” in his career, and it involves Paul Thomas Anderson — a near-miss that could have completely altered the trajectory of his career, and Hollywood, in the late ’90s.

In a terrific new Esquire cover story conversation between the actor and his “One Battle After Another” director, DiCaprio revealed that his biggest regret was passing on Anderson’s “Boogie Nights” nearly 30 years ago.

I’ll say it even though you’re here: My biggest regret is not doing “Boogie Nights.” It was a profound movie of my generation. I can’t imagine anyone but Mark [Wahlberg] 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 [about regrets], but it’s true.

As the story goes, Anderson wanted DiCaprio to play Eddie Adams, the high-school dropout who becomes adult film star Dirk Diggler, after seeing him in 1995’s “The Basketball Diaries.” However, DiCaprio had already committed to “Titanic,” the James Cameron epic that turned him into a global superstar. He even suggested Anderson cast his “Basketball Diaries” co-star Mark Wahlberg instead. The rest is history.

Fast-forward to 2025, and DiCaprio and Anderson have finally made their first film together. “One Battle After Another,” which opens Sept. 26 from Warner Bros, stars DiCaprio as Bob Ferguson, a washed-up revolutionary trying to protect his teenage daughter Willa (Chase Infiniti).

“I know One Battle After Another has been on your desk for a long time,” DiCaprio told Anderson during the interview. “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. 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 conversation between the two is fascinating. DiCaprio even tackles his own past work, which he rarely does. Anderson asks if he ever revisits his past films, and if there’s one that he’s rewatched the most times. His answer: Martin Scorsese’s “The Aviator.” Purely for nostalgic reasons.

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.” That’s simply because it was such a special moment to me. I had worked with Marty [Scorsese] on “Gangs of New York,” and I’d been toting around a book on Howard Hughes for ten years. I almost did it with Michael Mann, but there was a conflict and I ended up bringing it to Marty. 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. I felt responsible in a whole new way. I’ve always felt proud and connected to that film …

It’s a candid, funny, and surprisingly reflective exchange — the kind of back-and-forth you rarely get in celebrity profiles nowadays. DiCaprio and Anderson slip easily between personal history, artistic process, and decades-old Hollywood what-ifs, making it feel less like a formal interview and more like two old friends catching up after years of near-misses.