Leonardo DiCaprio, 50, Feels 32, Regrets Skipping ‘Boogie Nights’

Hollywood legend Leonardo DiCaprio usually keeps his personal life under wraps. But in a surprising chat, the Oscar winner pulled back the curtain. He opened up about his age, old regrets, and even watching his own movies.

The candid conversation happened with screenwriter and director Paul Thomas Anderson. Their talk for Esquire magazine came out on Wednesday, August 13. Anderson, who directed ‘One Battle After Another,’ got Leo to spill some tea.

Forever 32?

DiCaprio just turned 50 last year. Yet, when asked how old he would say he feels, he answered quickly. "32," he declared. He was 32 years old in the early 2000s, a successful period for him.

Anderson, 55, then brought up the real question Esquire wanted to ask. "You turned 50 last year," Anderson said. "Does it feel like a natural time to reflect?" DiCaprio joked back, "You emotionally turned 35 last year." This was another hint that he doesn’t quite feel his age.

"Your age is 50, but your emotional maturity is 32," Anderson teased. He asked Leo how that felt. The director then made it clear the magazine wanted to know if hitting 50 meant a time for self-reflection and growth.

DiCaprio explained that getting older makes him want to be more honest. He doesn’t want to waste time anymore. "I can only imagine how the next few decades will unfold," he shared. "For example, I see my mother. She says exactly what she thinks and doesn’t waste time. She doesn’t spend time pretending anything."

The ‘Wolf of Wall Street’ actor pointed out that as you age, your view on things really shifts. "Being more direct and risking things falling apart, or disagreements, or separating from any type of relationship in life—personal or professional—it’s just that you don’t want to waste time anymore," DiCaprio continued. "You have to be much more direct. It’s almost a responsibility because much more of your life is behind you than ahead."

A Big Regret and a Favorite Film

Looking back on his acting journey, DiCaprio shared his biggest career regret with Anderson. "I’ll say it even though you’re here: my biggest regret is not doing ‘Boogie Nights’," DiCaprio admitted. He was talking about Anderson’s hit 1997 film. "It was a very important movie for my generation."

He added, "I can’t imagine anyone else but Mark [Wahlberg] in that role. When I finally saw that movie, I thought it was a masterpiece. It’s ironic that you’re the one asking that question, but it’s true."

While DiCaprio was late to appreciate ‘Boogie Nights,’ he doesn’t often rewatch his own movies. "I rarely watch any of my movies," he confessed. "But if I’m honest, there’s one I’ve seen more than others. It’s ‘The Aviator’."

He shared why that film stands out. "It was just a very special moment for me," he revealed. "I had worked with Marty [Scorsese] on ‘Gangs of New York,’ and I had carried a book about Howard Hughes for 10 years." DiCaprio remembered almost making it with Michael Mann, but a conflict came up. So, he presented the idea to Marty Scorsese instead.

"I was 30 years old," DiCaprio recalled. "It was the first time, as an actor, I felt implicitly part of the production. I wasn’t just a hired actor playing a part." He praised the experience, adding, "I felt responsible in a whole new way. I’ve always felt proud and connected to that movie. I see it as a key part of my growth in this industry and of taking on the role of a true collaborator for the first time."