Filling in as a specialguest interviewer forEsquire,Paul Thomas Andersonrecently interviewedLeonardo DiCaprioin the lead-up to theirlong-awaited collaboration,One Battle After Another, which releases in theaters this September. It’s ridiculous that it took this long for these two, both masters of their respective craft, to team up, but we’re glad the stars finally aligned, as Anderson’s new film, a hybrid of rip-roaring action and biting social commentary, is poised to be a major step-up for him as a commercial filmmaker.
In this fascinating and insightful interview, Anderson and DiCaprio discuss many things, including the latterturning down a chance to star inBoogie Nightsand their mutual love forMidnight Run, but one of the most revelatory points comes from DiCaprio’s admission of his favorite film of his own to watch repeatedly, and it’s notTitanicorThe Wolf of Wall Street, but rather,The Aviator, afilm that helped transcended him from A-list movie star to creative collaborator with auteur directors.

Leonardo DiCaprio Loves to Re-Watch ‘The Aviator’
Most actors prefer not to watch themselves on screen or hear their voice, so it’s normal for them to reveal that they don’t revisit their past filmography. This self-consciousness also applies to non-professional actors–voice confrontation is a universal phenomenon.Oscar-winner Leonardo DiCapriois no different, ashe told Paul Thomas Anderson that he “rarely” watches anything he’s in.There’s one exception: his second collaboration withMartin Scorsese,The Aviator, the historical biopic about the life of the eccentric filmmaker, business magnate, and pilot,Howard Hughes.
“It was such a special moment to me,” DiCaprio said of his experience playing Howard Hughes in Scorsese’s 2004 Oscar-winning film, and why he keeps returning to it.“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,“the actor told Anderson, who has become a producer in his own right. “I felt responsible in a whole new way,” he continued. With his producing credit onThe Aviator, which was initially planned to be aMichael Mannfilm, DiCaprio convinced Scorsese, whom he had just worked with onGangs of New York, to tackle this film about the rise and fall of Hughes that tickled the director’s interests in Golden Age Hollywood.

By his account, the film gave him the confidence to treat himself as a tight-knit collaborator with every director. DiCaprio’s mission statement as an artist revolves aroundworking with the most accomplished visionariesworking today, including Scorsese,Quentin Tarantino,Christopher Nolan,Alejandro Iñárritu, and now, at long last, Paul Thomas Anderson.
What ‘The Aviator’ Represented in Leonardo DiCaprio’s Career
The Aviatorwas indeed a major step-up for DiCaprio, who was 30 years old at the time. Earning his second Oscar nomination for his arguably career-best performance as Hughes,DiCaprio’s graduationfrom baby-faced matinée idol to prestigious leading man with versatile dramatic chops was completeafter struggling to attain credibility inGangs of New York, where he feels overmatched by the film’s grandeur and powerhouse performance byDaniel Day-Lewis. From this point forward, he refused to play anything like the teen heartthrob fromTitanic, but instead, complex, morally ambiguous (if not downright evil) characters that challenge his movie star persona.
“I can stop and watch it anytime,” Anderson said ofThe Aviator, and it’s hard to argue with him. Despite its framing as a “serious,” Oscar-worthy movie about Hollywood history, the film is a blast to watch, gliding through its near-three-hour runtime with ease. Oozing with style thanks to its immersive production design, distinct color palette to signal a shift in time, and lavish costumes,Martin Scorsese channels his old Hollywood masters by helming an epic filled with comedy, drama, romance, andbravado set pieces. With so many unique chapters and sections of the film, from Hughes' days as a stubborn but imaginative filmmaker to an obsessive, self-destructive pariah, both aspects Scorsese likely relates to,The Aviatoris a perfect cable movie to jump in and out of.

It’s no surprise that Leonardo DiCaprio holdsThe Aviatorin such a high regard, asit represented the blueprint for the rest of his career.By completelytransforming into Howard Hughes, which required a distinct accent and tics stemming from his personal demons and ailing health, DiCaprio found an avenue to avoid being a generic, pretty movie star. In the future, we could buy him as the street-tough undercover cop from South Boston inThe Departed, a nefarious slave owner inDjango Unchained, or a bumbling, disillusioned, C-list actor inOnce Upon a Time… in Hollywood. More than anything, despite having no directing credits to his name, DiCaprio has an auteur status that lends all his films immediate prestige thanks to the artistic collaboration he latched on to inThe Aviator.
The Aviatoris available to stream on Paramount+ in the U.S.
The Aviator

