With a stellar career, international recognition, and a trophy case full of accolades, Oscar-winning actor Leonardo DiCaprio may seem to have it all. However, even the golden boy of Hollywood has a persistent regret.
Surprisingly, it has nothing to do with the fact that ‘Once Upon a Time in Hollywood’ did not win an Academy Award.
Working with some of the greatest filmmakers of all time, including Quentin Tarantino, Steven Spielberg, and Martin Scorsese, DiCaprio has amassed one of the most impressive filmographies in cinema over the course of more than thirty years.
What is Leonardo DiCaprio’s biggest regret?
DiCaprio acknowledged that there is one role he still wishes he had taken in a recent interview with Paul Thomas Anderson for Esquire.
“I’ll say it even though you’re here: My biggest regret is not doing Boogie Nights,” DiCaprio told Anderson. “It was a profound movie of my generation. I can’t imagine anyone but Mark [Wahlberg] in it. When I finally saw it, I thought it was a masterpiece.”
At the time, Anderson was just 27 years old and already being hailed as a filmmaking prodigy. His 1997 drama about the rise and fall of the porn industry in California became a cultural touchstone but it could have starred DiCaprio.
The career-changing choice DiCaprio made for ‘Titanic’
Back in the mid-’90s, Anderson had his sights set on DiCaprio for the role of Dirk Diggler, a character requiring raw vulnerability. But DiCaprio had already committed to another little project, ‘Titanic.’
Instead, DiCaprio recommended his The Basketball Diaries co-star Mark Wahlberg for the role. Anderson took his advice, and Wahlberg’s performance transformed him from a former rapper and model into a serious Hollywood actor.
Even though Titanic ended up becoming one of the highest-grossing films ever made, DiCaprio has publicly questioned how Boogie Nights might have changed the course of his career.
This is not the first time he has thought about the choice; in a 2008 GQ interview, Titanic director James Cameron joked that he would make a different choice “if you could go back.” DiCaprio’s response? “I’m not claiming that I would have.
However, it would have taken a different path in terms of career. I wish I could have done both of them because I think they’re both fantastic.
Leonardo DiCaprio’s upcoming movies
Some of Hollywood’s most renowned directors are involved in Leonardo DiCaprio’s exciting upcoming projects. First up is Paul Thomas Anderson’s darkly humorous action-thriller, One Battle After Another, which is scheduled for release on September 26, 2025.
The movie, which is based on Thomas Pynchon’s 1990 book Vineland, centres on a group of former revolutionaries who get back together after 16 years to save a comrade’s daughter who has gone missing.
DiCaprio plays Bob Ferguson, and the cast includes Sean Penn, Benicio Del Toro, Regina Hall, and Teyana Taylor.
DiCaprio is also set to star in a biopic about cult leader Jim Jones, though that project is currently on hold. DiCaprio will also reunite with Martin Scorsese for Roosevelt, a biographical drama about President Theodore Roosevelt.