Leonardo DiCaprio Reveals His Favorite Film and Biggest Career Regret

In a candid 2025 interview with Esquire, Leonardo DiCaprio said the only movie he watches more than once is The Aviator, and that his biggest career regret is turning down Paul Thomas Anderson’s 1997 film Boogie Nights.

DiCaprio’s Hollywood debut came in the late 1980s with television commercials and a recurring role on the sitcom Parenthood. He earned his first Academy Award nomination for What’s Eating Gilbert Grape (1993) and catapulted to worldwide fame with Titanic (1997). After that blockbuster, he sought roles that would broaden his range, leading to collaborations with director Martin Scorsese.

Their partnership began with Gangs of New York (2002) and continued with The Aviator (2004), The Departed (2006), Shutter Island (2010), The Wolf of Wall Street (2013), and Killers of the Flower Moon (2023).

In the Esquire interview, DiCaprio explained that The Aviator was the first time he felt “implicitly part of the production” rather than merely an actor hired to play a role. He added that at 30 he had “a responsibility in a whole new way” and that the film remains a key part of his growth in the industry.

The biopic, directed by Scorsese and written by John Logan, stars DiCaprio as Howard Hughes and features Cate Blanchett as Katharine Hepburn and Kate Beckinsale as Ava Gardner. The film’s production involved extensive research and a large crew, and it earned DiCaprio critical acclaim and a nomination for Best Actor.

DiCaprio’s regret, on the other hand, dates back to the mid‑1990s. According to the same interview, he declined the lead role in Boogie Nights because he was committed to Titanic at the time. Boogie Nights, written, directed, and co‑produced by Paul Thomas Anderson, premiered at the Toronto International Film Festival on September 11, 1997, and was released by New Line Cinema on October 10, 1997. The film follows a young dishwasher who becomes a pornographic star during the Golden Age of Porn in the 1970s.

Mark Wahlberg played the protagonist, Eddie Adams, and the film earned three Academy Award nominations, including Best Original Screenplay for Anderson. DiCaprio said that when he finally watched the movie, he considered it a “masterpiece.” He expressed that he wished he had taken the role, noting that the part was a “profound movie of his generation.”

The decision to pass on Boogie Nights illustrates the trade‑offs actors face when scheduling projects. DiCaprio’s choice to prioritize Titanic — which became the highest‑grossing film worldwide at the time — meant missing an early collaboration with Anderson that would later become a celebrated work in American cinema.

Both The Aviator and Boogie Nights have had lasting influence. The Aviator remains a benchmark for biographical dramas, while Boogie Nights is frequently cited in film studies as a landmark of 1990s independent filmmaking. DiCaprio’s reflections highlight how a single career decision can shape an actor’s legacy.

As of September 2026, DiCaprio continues to produce and star in high‑profile projects, including the 2025 action film One Battle After Another. His candid comments about his favorite film and biggest regret offer insight into the choices that define a Hollywood career.