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Leonardo DiCaprio Shares His Biggest Career Regret in Hollywood, ‘It was a profound movie’

In a recent sit-down with director Paul Thomas Anderson, Leonardo DiCaprio opened up about the biggest regret in his Hollywood career. He also shared a special movie from his filmography.

Published By: Deepanshu Sharma
Last Updated: August 14, 2025 15:13:12 IST

Leonardo DiCaprio is one of those performers who manages to peak viewer interest while balancing a healthy personal life. Over the years, the actor has delivered consistent performances, raising the bar in every movie. From performances that require seriousness (The Revenant) to characters that tickle the funny bone (Catch Me If You Can), DiCaprio has aced every role. However, not even the best are perfect. In a recent interview with Esquire, Leonardo DiCaprio opened up about the one film he regrets not doing. 

Leonardo DiCaprio shares his Biggest Regret in Hollywood

In an interview for Esquire, DiCaprio was sitting across director Paul Thomas Anderson for the promotion of their upcoming film One Battle After Another. For the opening question, Anderson simply asked the actor about any regrets in his career. 

The Once Upon A Time in Hollywood actor then told the famed director that his biggest regret is not doing Boogie Nights (1997). The movie is directed by Anderson himself and stars Mark Wahlberg in the lead role.

“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,” DiCaprio said. “ I can’t imagine anyone but Mark in it, ” he continued before pointing out the irony that Anderson himself is the person asking him the question.

The Only Movie Leonardo DiCaprio Loves Watching

Halfway through the interview, the There Will Be Blood director asked DiCaprio, “Do you ever watch any of your old movies?” The actor who generally refrains from watching himself admits to Anderson that the only movie he has rewatched from his filmography is The Aviator (2004).

“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,” the actor told Anderson. 

Continuing his answer, he shared that the reason The Aviator is an exception to him is that it served as a landmark film in his journey in Hollywood. It marked his transition from just an actor to a collaborator. 

“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,” the Inception actor told Anderson.

The movie became another feather in his cap. The Aviator was nominated for 11 Academy Awards and won 5 awards in the category.

Leonardo DiCaprio and Paul Anderson Team up For One Battle After Another

After years of waiting, Leonardo DiCaprio and Paul Thomas Anderson have finally teamed up to bring fans their upcoming action thriller, One Battle After Another. The movie is written, directed and produced by Anderson himself and stars DiCaprio as Bob Ferguson, an ex-revolutionary on a rescue mission. 

It also stars Sean Penn, Benicio del Toro, Regina Hall, Teyana Taylor, and Chase Infiniti in key roles and is slated to release on 26th September 2025.

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© Copyright ITV Network Ltd 2025. All right reserved.