by Brad Pitt has built a reputation as one of Hollywood’s most daring and committed actors, willing to transform himself physically and psychologically to inhabit whatever role comes his way. From the deranged early work of Kalifornia and Twelve Monkeys to prestige dramas like The Curious Case of Benjamin Button and Moneyball, Pitt has never shied away from challenging material.
However, in a shocking confession, Pitt recently admitted that there was one role that truly intimidated him: that of Cliff Booth in Quentin Tarantino’s Once Upon a Time in Hollywood. Speaking to Esquire magazine, Pitt acknowledged that he had never felt such trepidation about taking on a character before, despite his decades of risk-taking on screen.
“I don’t think I was ever fearful of taking on a role before,” Pitt explained. “This one was different. When Quentin approached me, I had to really think about it—more than usual.”
What was it about the role of Cliff Booth that gave even a veteran like Pitt pause? According to the actor, it came down to the exceptional complexity and ambiguity of the character on the page. Cliff was not just the laidback stuntman sidekick to Leonardo DiCaprio’s western star Rick Dalton; Tarantino had written him as an enigma, a shape-shifter with murky motivations.
“I realized I didn’t understand this guy, and I couldn’t readily identify his motivations,” Pitt said. “It was on the page, but there was something mysterious about this character that was challenging for me to get a handle on.”
In a role that required him to act as Dalton’s driver, handyman, and drinking buddy, Booth came across as the consummate Hollywood survivor, adapting to fit whatever role was required in order to get by. But his complex backstory, including rumors that he murdered his wife, hinted at darkness beneath the stoic surface.
“There were all these ambiguities and subtleties about Cliff’s relationships and backstory that were fascinating on the page, but difficult to convey on screen,” Pitt explained. “I liked that dichotomy, but it definitely made me unsure at first about whether I could really pull it off.”
Indeed, Pitt’s first instinct was to turn down the flashy part in Tarantino’s love letter to 1960s Hollywood. It was the director’s powers of persuasion that ultimately convinced Pitt to take the plunge.
“Quentin made his case for why he thought I was the right fit for Cliff, and as we talked more, I started to understand his vision,” Pitt said. “Eventually that tipped me over the edge to say yes, but I knew going in that this was a complex performance I couldn’t just wing based on instinct.”
To prepare, Pitt embarked on an intensive process of character study, collaboration, and research. It began with lengthy conversations with Tarantino about who Cliff was at his core: what drives him, what does he care about, what does he fear? Together, they formed a backstory that explained Cliff’s motivations while preserving his essential mysteriousness.
Pitt also spent hours discussing the role with co-star Leonardo DiCaprio, who had already signed on to play Rick Dalton. Their dynamic was just as central to the film as Dalton himself, so developing an off-screen rapport was crucial.
“Leo and I spent a lot of time just bouncing ideas off each other, figuring out how to convey the complexity of Cliff and Rick’s friendship,” Pitt explained. “We did a lot of improvisation and scenario work to find the little details that create that authenticity on screen.”
Finally, Pitt delved deep into research on stunt work in 1960s Hollywood, studying how stuntmen of the era behaved on and off set. He took lessons in driving and fight choreography, and even consulted with modern stunt coordinators to discuss how the job has (and hasn’t) changed over the decades.
“The more research I did into the realities of Cliff’s job and that time period, the more it helped me understand his mindset,” Pitt said. “It gave me the confidence I needed to finally just inhabit this guy.”
When cameras finally rolled on Once Upon a Time in Hollywood, that confidence paid off in a big way. Pitt delivers arguably his best performance ever as the enigmatic Cliff Booth, perfectly embodying the character’s relaxed charisma, wry humor and simmering violence. Critics hailed it as a career-defining tour de force.
For his part, Pitt agrees that the role represents a high point, precisely because of the risks it required him to take.
“This was definitely one of the most challenging roles of my career,” he admits. “I had to leave my comfort zone and approach the character from an uncertain place. But that’s where the magic happens. I never feel more alive as an actor than when I’m a little bit scared like that.”
Pitt’s outstanding performance opposite DiCaprio earned him rave reviews and his third Oscar nomination for Best Supporting Actor. Clearly, confronting his fears paid dividends, proving once again that he is one of the most committed, daring actors in Hollywood.
“I don’t see the point in roles unless they force you to stretch and take risks,” Pitt concludes. “This was the scariest leap I’ve ever taken, but now I just want to find that next challenge, that next fear to embrace.”
After a three-decade career defined by bold choices, it’s clear that a little fear will never stop Brad Pitt from plunging into daring, complex roles that allow him to push the boundaries of his talent. Whether he’s fighting zombies, unraveling conspiracies, or driving through 1960s Hollywood, Pitt’s willingness to take on challenges has made him one of the most captivating stars cinema has ever seen. If Once Upon a Time in Hollywood represented his most intimidating role yet, one can only imagine what thrilling risks he will embrace next.
