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Quentin Tarantino on New Movie with Leonardo DiCaprio, Brad Pitt & Margot Robbie

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Quentin Tarantino turned Jimmy Kimmel’s stage into a red carpet launch pad four nights before his ninth movie hit theaters.

The July 22, 2019 episode of Jimmy Kimmel Live! doubled as a live remote for the Los Angeles premiere of Once Upon a Time in Hollywood, staged directly across Hollywood Boulevard from Kimmel’s studio. Leonardo DiCaprio and Margot Robbie hijacked the monologue on their way to the carpet, and Brad Pitt made his own walk-through before Tarantino sat down for the interview. What followed was a loose, candid conversation about the film’s cast, Tarantino’s writing process, and his long-stated plan to stop directing after ten movies.

• DiCaprio and Robbie interrupted Kimmel’s monologue to invite the studio audience across the street to the premiere screening, with Pitt following for his own walk-through cameo.
• Tarantino told Kimmel he decided to kill Adolf Hitler in Inglourious Basterds after writing the note “Just f—ing kill him” late one night, sleeping on it, and waking up convinced it worked.
• Tarantino reaffirmed his plan to retire from directing after his tenth feature, explaining he’d rather leave before the quality of his work started slipping, while keeping the door open to theater, television, and writing.

A Premiere Takes Over the Monologue

Kimmel’s show sits close enough to the TCL Chinese Theatre that the network turned the geography into a bit. DiCaprio and Robbie, both dressed for the carpet, walked into frame mid-monologue and told the audience flat out to come with them, pointing across the street toward the premiere. Pitt’s cameo came later in the same stretch, a quick walk-through rather than a sit-down, saving the extended conversation for Tarantino once the show settled into its interview segment.

It was a stunt built for a night when the movie’s own publicity machine and a late-night broadcast happened to occupy the same block. Robbie also came back for a separate guest appearance before the episode wrapped, closing the loop on a night that had already sent half the studio audience across the street once.

The Note That Killed Hitler

Tarantino used part of his sit-down to revisit Inglourious Basterds, the 2009 film that rewrote World War II by having a cinema full of Nazi officers, Hitler included, die in a fire set by Jewish-American soldiers and a French theater owner. Tarantino told Kimmel the decision wasn’t some elaborately plotted structural choice — it came down to a scrap of paper.

Just f—ing kill him.

According to Tarantino, he wrote that line down late one night while working on the script, went to sleep without second-guessing it, and woke up still convinced it was the right call. It’s the kind of blunt, unglamorous account of a landmark scriptwriting decision that Tarantino has never been shy about sharing in interviews — he’s built a reputation for direct answers even when the subject turns pointed, a trait that’s shown up in some of the tenser exchanges collected in our roundup of stars silencing disrespectful interviewers.

Casting DiCaprio, Pitt, and Robbie

Once Upon a Time in Hollywood marked Tarantino’s third film with DiCaprio in a lead role, his second with Pitt, and his first with Robbie, and the interview touched on how he approaches asking actors to join his projects. Tarantino discussed the collaboration in terms of trust built over separate careers — DiCaprio and Pitt playing off each other as, respectively, a fading TV Western star and his stunt double, with Robbie rounding out the ensemble. The chemistry on display during the monologue hijack, three stars moving between a talk show set and a red carpet without missing a beat, was the kind of easy rapport that’s notably absent from some of the pairings chronicled in pieces like actors who treat their co-stars like trash.

The Ten-Film Rule

Kimmel pressed Tarantino on a plan the director has repeated for years: stop directing after ten feature films. Once Upon a Time in Hollywood was his ninth. Tarantino explained the thinking isn’t about burning out on filmmaking itself — it’s about avoiding the stretch where a director’s work quietly declines while everyone around him pretends not to notice. He told Kimmel he’d rather step away on his own terms than keep making movies past the point where they’re his best work, though he left plenty of room for theater directing, television, and writing once the tenth film is done.

Closing the Premiere Loop

Robbie’s second appearance of the night, dropping in to close out the episode after already crossing the street once for the carpet, gave the broadcast its bookend. Once Upon a Time in Hollywood opened in theaters four days later, on July 26, 1969-set nostalgia and all, with the Kimmel stunt standing as the loudest piece of promotion the film got outside the premiere itself.