Leonardo DiCaprio has shared his biggest regret in Hollywood, revealing a missed opportunity that still stands out for him. He expressed regret about not being part of the movie Boogie Nights, describing it as a defining film of his generation and praising its impact. DiCaprio acknowledged that Mark Wahlberg was the perfect fit for the role, but still views the movie as a masterpiece he wishes he had been involved in.
Why The Aviator Holds a Special Place for DiCaprio
Among all the films he has starred in, DiCaprio admits The Aviator is the one he watches most often. The actor explained this film marked an important phase in his career, as it represented his transition from simply playing roles to becoming a true collaborator in the production process. After years of preparing for the role of Howard Hughes, DiCaprio was able to work closely with director Martin Scorsese, creating a lasting personal connection to the project.
“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 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.”
— Leonardo DiCaprio
Choosing Film Projects with Intent
DiCaprio’s reflections also highlight his careful selection of roles throughout his career, often opting to take on projects that offer personal growth and meaningful collaboration rather than simply adding to his filmography. This approach demonstrates his commitment to balancing professional achievements with a sense of purpose and creative fulfillment.
