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Quentin Tarantino has had varying levels of difficulty shooting his many films. But there was only one he ranked as the most challenging when it came to capturing it on the big screen.

Quentin Tarantino on the hardest film he’s ever made

Quentin Tarantino posing after winning the 2023 Prix Fitzgerald at Hotel Belles Rives.
Quentin Tarantino | Jacopo M. Raule/Getty Images

Tarantino has traveled all over the world to shoot his movies. But ironically, it was shooting in a place that the filmmaker was very familiar with that provided the most challenge. His latest film, Once Upon a Time in Hollywood, was set in Los Angeles during Hollywood’s golden age in the 1960s. But shooting the film around Los Angeles in real life took some maneuvering for the filmmaker.

“In the past, say on Jackie Brown, that was me just going around shooting Los Angeles. But for this film, as far as I’m concerned, I might as well be shooting Moscow,” Tarantino said in an interview with Uncut. “Films like Inglourious Basterds, Django Unchained and The Hateful Eight were set-bound. Here, we’re actually shooting all over Los Angeles. Los Angeles is a character in the story and nothing is like the way it was in 1969. We have to create everything. It’s the hardest film I’ve ever had to make.”

Tarantino’s own background may have helped inform him on Once Upon a Time…’s aesthetic. Growing up in the 1960s and 70s, he was in tune with what was going on in the LA entertainment industry around him.

“I was very aware of the whole counterculture, too. You couldn’t turn on television without seeing hippies, you’d see hippies on the street. Most of the babysitters that I ever had were hippies,” he said.

Tarantino captured a similar vibe for Once Upon a Time in Hollywood.

“I just like creating this time of hippie Hollywood, and I like telling the story through two characters who are outside of the gate of hippie Hollywood – who didn’t realise that it was gonna change and can’t believe it changed so quickly,” Tarantino added.

Where Quentin Tarantino ranked ‘Once Upon a Time in Hollywood’ among his work

Tarantino has one of cinema’s most respected filmographies. Almost all of his movies enjoyed praise and acclaim from the majority of critics. Because of this, many fans have differing opinions on what they consider Tarantino’s best film. Tarantino used to have a difficult time picking out his favorite movie as well until Once Upon a Time in Hollywood.

“For years people used to ask me stuff like that,” Tarantino said on The Howard Stern Show. “And I would say something like, ‘Oh, they’re all my children.’ I really do think ‘Once Upon a Time in Hollywood’ is my best movie.”

Although he’s had trouble picking his favorite in the past until Once Upon a Time, it wasn’t hard for Tarantino to name his worst.

Death Proof has got to be the worst movie I ever made,” Tarantino once said on The Hollywood Reporter (via IGN). “And for a left-handed movie, that wasn’t so bad, all right? So if that’s the worst I ever get, I’m good. But I do think one of those out-of-touch, old, limp, flaccid-dick movies costs you three good movies as far as your rating is concerned.”

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Death Proof didn’t reach the same heights as Once Upon a Time in Hollywood or Pulp Fiction. But Tarantino believed the movie’s performance was due to it not translating well for its intended audience. Death Proof was a part of a double feature that included the Robert Rodriguez film Planet Terror.

Presented together, this pair of movies was titled Grindhouse in theaters, which was supposed to be a throwback to classic features. But Tarantino felt the audience wasn’t receptive to the idea back then.

“With Grindhouse, I think me and Robert just felt that people had a little more of a concept of the history of double features and exploitation movies. No, they didn’t. At all. They had no idea what the f*** they were watching. It meant nothing to them, alright, what we were doing,” Tarantino once told Empire.