Why Cliff Booth is one of Tarantino’s greatest characters (contains spoilers)


First off, nothing I say should be taken as gospel with regards to Quentin Tarantino’s intended messaging in Once Upon a Time in Hollywood. But in the words of the American treasure himself, I reject your hypothesis. I reject the idea that films do not belong to the audience after their release. Our collective and individual interpretations of art are the only things distinguishing art from business presentations or show-and-tell. 

That being said, Cliff Booth (Brad Pitt) is one of Tarantino’s greatest creations because he is so very flawed. And he also represents the thesis of the entire film.

To begin with, his demeanor as conveyed by Pitt is pitch-perfect. He’s always behind his friend and boss, Rick Dalton (Leonardo DiCaprio), a 60s cowboy actor for whom Cliff does stunt work, electrical work, chauffeuring, and basically anything else Rick’s heart desires. Dalton appears smooth and timelessly cool in his film and television projects, but off-camera he can be quite paranoid and neurotic. But Cliff, a consummate friend, never lets his buddy’s outbursts cloud his judgment. Cliff knows Rick is always going to have his back, and Rick knows Cliff will be loyal til the end. It’s a charming dynamic that never wears out its welcome, especially since Tarantino wisely rations out scenes of them together and scenes of one without the other. We get a sense of a deep inner life in both men, even though their immediate concerns may seem surface-level on first glance.


Cliff’s inner life starts becoming apparent when he finally leaves his friend’s company at the end of the first of just a few days the film chronicles. He zooms though downtown Los Angeles, cool but pensive, music blaring through his car stereo as it often does throughout the movie. Finally arriving at his trailer near a run-down oil derrick and a drive-in theater, he greets his pit bull and serves him canned dog food, while preparing himself a gourmet dinner of Kraft macaroni and cheese. In any other movie, this scene would not even exist. But this is easily Tarantino’s most thoughtful film in a decade, and just by sheer fact of the scene’s length, we can tell there’s more to Cliff than being a dead ringer for a young Robert Redford. He’s cool in a very specific way that not many Tarantino characters are: he’s not after power, revenge, or even really completing any sort of complex task. He’s just found his niche in life, and he’s okay with that. As long as he can still make it known that he’ll always be the coolest guy in the room.

That’s where the Bruce Lee (Mike Moh) sequence comes in. It’s part of a daydream of Cliff’s — perhaps partly true, perhaps entirely fantasy — in which he ponders what might happen if he tried to get a stunt job on Rick’s latest shoot, which he’s been told already would be tough. He knows instinctively that Rick would stand up for him, but he also knows he might just fuck it all up for himself by getting in a fight with an important cast member. It doesn’t specifically need to be Bruce Lee. But I think the reason it is is that Cliff genuinely dislikes this new style of action star, and could easily see himself getting in a confrontation with one. It doesn’t seem so much about Tarantino knowing Lee’s off-screen persona, it’s more about Cliff knowing himself and his faults. And because this daydream sequence is so long, the payoff is all the more surprising and kind of sexy in a cinematic way when we simply cut back to Cliff fixing Rick’s TV antenna, smiling and nodding to himself. 

Within that daydream sequence, we learn why it is that Hollywood no longer takes kindly to Cliff. It’s widely believed he murdered his wife, and Cliff remembers the moment that was said to have taken place, but we never see the payoff. From then on, it’s an open question as to his guilt or innocence. But we could infer through his outbursts of violence that it wouldn’t be beyond him. Then again, he’s so charming and nice in so many situations throughout the film that it’s easy to see both sides. This is why I find him such a fascinating character and why I think he represents the entire backbone of this film. The central questions of Once Upon a Time in Hollywood seem to me to be these: 1. can our macho cinematic idols exist today in the same collective imagined mythos that they always have? 2. Or do we need to reckon with our love for them and examine this love through the lens of the modern phrasing of toxic masculinity, the activity of which of course existed then and exists today? It seems to me the film answers the latter in the affirmative. 


My interpretation obviously must take into account Cliff’s last two big scenes: Spahn Movie Ranch and the film’s finale at Rick’s house. The scene at Spahn Movie Ranch rivals my overall favorite individual scene in the movie, which is Rick’s extended scene in the saloon leading up to his flub. What’s so perfect about the Spahn Ranch scene is that the tension never lets up, even as the pacing of the thing can seem very, very loose at times. When Cliff confronts Squeaky (Dakota Fanning) about George Spahn’s (Bruce Dern) condition, we’re incredibly suspicious because Cliff is suspicious, and because of what we know about the Manson Family. But that tension doesn’t evaporate when Cliff finds George alive and relatively well because Tarantino immediately puts more obstacles in Cliff’s way. His patience has been tested throughout the entire sequence, and only when there really is no other option will he resort to violence. It seems to him there’s no other way to speak to these fanatics in the desert, especially when they’ve messed with Rick’s car. The stakes of this moment for Cliff and the endless provocation from the “hippies” necessitates Cliff teaching one of them a lesson. It’s not gratuitous in this instance and it doesn’t put Cliff in the realm of toxicity. 

What crosses the line for many, and indeed crosses the line into toxicity for me, is his zeal in dispensing with the Mansonites that come for him and Rick at the end. As violent and over-the-top as this sequence is, however, I totally understand why it was done this way and it actually enhances my appreciation for the way Cliff fits into the thematics of the film and Tarantino’s filmography and legacy. 

It’s been said plenty of times that the film plays out as a fairy tale for old Hollywood. That’s true, but on another level, I think the film is about the beginning of polarization in America. Rick and Cliff label every young person they see on the streets of L.A. as “hippies,” but there’s no colloquial distinction for them between “hippies” and Mansonites, even though Cliff definitely understands the difference after the Spahn Ranch scene. But basically anyone that’s not trying to achieve relative success the way they’re trying to is, in their eyes, a “hippie,” while they look up to all the real-life stars who we know have their own demons, but they really know nothing about.

The Mansonites are similarly quick to judgment. The Manson devotee who Cliff flirts with (Margaret Qualley) screams at him and calls him blind when he’s simply trying to leave Spahn Ranch. You could say that the cult members are afraid of Cliff calling the police, but they don’t have any proof that he would. They simply have their own prejudices and act on them, just like Rick and Cliff. (Of course, the Manson Family wanted to ignite a race war.)


When Tarantino gets into re-writing the history of the night of Sharon Tate’s (Margot Robbie, excellent as ever) death, the Mansonites’ reasoning for wanting to kill Rick rather than those in Tate’s home right next to Rick like they were told basically comes down to MPAA logic. People like Rick and Cliff have “taught them to kill,” so why shouldn’t they practice what they’ve been taught? This cheap media analysis emboldens their bloodlust, and even on acid, Cliff can see right through them. Though they’re still “crazy hippies” to him, which is not entirely accurate, they’re objectively in the wrong, and it’s truly cathartic to watch Cliff (and Rick with the flame thrower of course) give them what they deserve. 

The two sides are not willing to talk to one another or see each other beyond their vague preconceptions. People like Rick think they’re totally superior to everyone else, even though they came from humble beginnings themselves (Rick mentions he might have to ‘go back to Missouri’), and the Mansonites assume the whole world is out to get them, so why shouldn’t they go out and get the world?

In the center of these factions stands Cliff. He is as much extreme counter-culture as he is old Hollywood. A tough but fair guy with a troubled past who behaves like a fish swimming upstream. While everyone else thrives on this notion of more wealth, more fame, or more power, he is just fine with his own small slice of the status quo. His penchant for fighting and solving problems through physical violence brings in the toxicity angle, however, and I think that’s what Tarantino is wrestling with here. 

There is no world in which a guy like Cliff stands as a model citizen. But that’s kind of the point. He represents what many of us love about the coolest of “cool” male figures in the films of old Hollywood and beyond. The film’s brutal third-act confrontation begs the question: is this town still big enough for the two sides of us?

As much as we may hate it, the answer seems to be what Cliff says when asked if he’s still working for Rick: still here.

-George Napper

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