For years we had been hearing about acclaimed filmmaking maestro Quentin Tarantino’s next project, a film he reportedly spent five years writing as if it was a novel. What was it about though? The reports were unclear. It had to do with the real-life 1969 murder of Golden Globe-nominated actress Sharon Tate and four others at the hands of members of Charles Manson’s cult in the Hollywood home she shared with her director husband Roman Polanski.

It was the story of Tate’s fictitious neighbour, Rick Dalton, a former 1950s TV western star, trying desperately to prevent his flagging career from riding off into the sunset along with Hollywood’s Golden Era. It followed Cliff Booth, another bit of Tarantino make-believe, who was once Dalton’s stunt double in the latter’s heyday but now finds himself as the actor’s Man Friday/only friend, his proverbial wagon tethered to Dalton’s due to dark rumours about his past leaving him persona non grata to the rest of Tinsel Town.

Which of these stories was Once Upon a Time in Hollywood actually about? All of the above? None of the above? Something abruptly different and esoteric? The answer is: Yes.

Arguably the least mass-consumption friendly film Tarantino has done for a while, Once Upon a Time in Hollywood is a juxtaposed mish-mash of story beats and filmmaking approaches. Equal parts rose-tinted love letter, true-crime drama, wistful mid-life crisis treatise, and even an ode to the art of filmmaking, finding a box to neatly stick this film into is a study in futility.

You never get the impression that the film has run away from Tarantino though. Every beautifully framed shot, every meaty line of dialogue is obviously deliberate. This is clearly the work of a master filmmaker who has meticulously curated his own art installation, right down to the ever-present soundtrack of contemporary hits to accompany his adult fairy tale version of Hollywood. But just because there’s no overt sloppy happenstance on display doesn’t mean it’s not a little bit of a mess.

At 161 minutes, Once Upon a Time in Hollywood is undeniably overlong. Large early chunks of that running time are devoted to meandering bouts of nothingness, following characters as they drive from one end of Los Angeles to another with zero discernible benefit to character or story. This is made especially frustrating by the fact that later events are conversely rushed by with nothing more than a hasty info-dump voiceover detailing off-screen events. Tarantino is too good of a director to have any of this ever get boring though. In fact, large bouts of it can be downright gripping and entertaining – including a gonzo-bizarro fever dream of a final act that has to be seen to be believed – but is it really necessary?

Most of why the material is still so engaging, despite a drought of narrative impetus in places, can be found in Tarantino’s cast, which includes a voluminous roll-call of the filmmaker’s favourite people to work with playing everybody from Steve McQueen to Bruce Lee. There are also a couple of breakout scene-stealers. As Dalton and Booth though, Leonardo DiCaprio and Brad Pitt act as our primary guides through the star-packed studio lots and sun-baked streets of Los Angeles.

And we couldn’t have asked for better leads as both men are firing on all thespian cylinders here, with DiCaprio required to do the bulk of the overtly dramatic heavy lifting. His Dalton is a fractured, anxious mess, having long drank away his former quintessential leading man status. Deep into the dregs of his career, he desperately claws at recognition, even considering the once-unthinkable offer from producer Marvin Schwarz (Al Pacino) to make spaghetti westerns over in Italy. It’s a powerhouse showing from DiCaprio, who gets to flex every different type of dramatic muscle he has and flexes them with Olympian intensity.

If Dalton is this film’s bleeding heart, then Pitt’s Booth is its sub-zero cool and bad-ass swagger though. With nothing going in his life except his dog – a pit bull named Brandy that’s one of those aforementioned scene-stealers – and Dalton’s wide-ranging employment (he’s everything from chauffeur to confidant to handyman), Pitt’s Booth is all gristle and grit. A man of action and disarming smiles. It’s mostly through his random interactions with zesty hitchhiker Pussycat (Margaret Qualley) that we get obliquely segue into the story of the Manson Family, leading to one of the film’s greatest scenes: a tense standoff at a dusty abandoned ranch. And Pitt simply owns it all. This is awards-level stuff.

Meanwhile, as Tate, Margot Robbie is positively luminous, effortlessly drifting in and out of the film’s beats with angelic charm as we follow her in the days leading up to that fateful August night. A night I hope you’ve read up on as Tarantino has zero patience for anybody not familiar with the murderous events of the summer of 1969. Members of the Manson Family, including cult leader Charles Manson himself, flit in and out of the film ephemerally, with next to nothing in the way of explanation or introduction. On the one hand, I find this lack of hand-holding refreshing, but it’s going to leave many viewers befuddled and frustrated.

Tying into this, how Tarantino chooses to handle Tate’s tragic moment in real-life history is probably going to be the make-or-break moment for many who see this film. It’s tough to discuss this without spoilers, but I will say that initially it didn’t quite sit right with me. After some introspection though, I realized what Tarantino was trying to say and I warmed to it considerably. This may undeniably be Tarantino at his most self-indulgent, but it’s also him at his most confident, making the type of bold meta-commentary that invites dissection. And a filmmaker of his ilk shirking off the fetters of conventionality – the little that has ever applied to him – is an experience I will never not appreciate.

And I guess that’s how I feel about Once Upon a Time in Hollywood overall. I appreciate everything Tarantino does here from a ballsy technical level (though it desperately requires an edit from somebody not as in love with their own labours to truly tighten it up), but I only love some of it. The film is steeped in ideas about the passing of one age to the next, of the old falling on their swords to make way for the young, of the eternal power of exuberant creativity and talent winning out in the end. With Tarantino infamously claiming this ninth feature film to be his penultimate creation before he calls it quits on the entire biz, you don’t have to squint too hard to see his own internal middle-aged turmoil of relevance amid his idolization of this golden memory he has of “his” Hollywood. There’s definitely enough greatness here to allay any fears if him losing his touch just yet, but still, this has easily been the most difficult of his films that I’ve ever had to review. I would predict the viewing experience to be the same for many.

Last Updated: August 29, 2019

Once Upon a Time in Hollywood
Quentin Tarantino's Once Upon a Time in Hollywood is a bold, ambitious, meticulously crafted, and magnificently acted fairy tale vision of a Tinsel Town that was and could have been. It's also undoubtedly the least mainstream film the acclaimed filmmaker has made in a while, and is overlong and potentially frustrating due to its narrative choices. A flawed bit of excellence.
7.5
/10
83/ 100

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