A movie about the Manson murders? Seems like a bad idea, some might say. It would be distasteful even in hands that were less known for leaning into extreme violence than Tarantino’s. But somehow, Once Upon a Time in Hollywood manages to deftly sidestep the elephant in the room, creating a narrative that is triumphant, even if it hits a few off notes in the final act.

Rick Dalton (DiCaprio) is a former movie star and TV cowboy whose career has been in a steady freefall throughout the 1960s, and is now reduced to making guest appearances on a string of new television shows. His growing alcoholism requires him to become more and more dependent on Cliff Booth (Brad Pitt), his former stunt double, chauffeur, and one true friend. Dalton has been so sidelined in Hollywood that even at his home, where he should be the most dominant figure, he’s framed as the next door neighbor of Roman Polanski and Sharon Tate (Margot Robbie).

And not to get ahead of ourselves, but this may be Leonardo DiCaprio’s finest performance. His Rick Dalton is fragile, narcissistic, and perfectly balanced between humor and despair (which way he leans depends on how many whiskey sours he’s had). Although Dalton is the lead within the narrative structure of the film, it’s fitting that his role is overshadowed by the specter of Sharon Tate that hangs over the entire production, turning him (despite his celebrity status) into a bit player in a much larger story.

Brad Pitt (certified hottie, by the way — has he ever been more attractive than he is here?) has somewhat less to do — his role largely hinges on him being cool and unflappable, qualities that known quantity Pitt can safely be relied upon to bring to the table. But the dynamic between Cliff Booth (Pitt) and Dalton is endlessly fascinating. It makes sense that Booth occupies this amorphous space in Dalton’s life, and his role as a stunt double is entirely fitting — a stunt double has no character in the script, he serves simply to step in when things get too hard for the lead actor.

Brad Pitt in Once Upon a Time … in Hollywood (2019) – © Sony Pictures Entertainment

Cliff never seems like an actual person — he has no inner life, or at least not in the way that Dalton does, no real home, no real job, and very few emotional connections. He’s just there to shoulder the burdens of Rick’s life. His past is handled in consistently vague terms — Cliff is described as a war hero, but we don’t know anything beyond that. We’re told by other characters that he murdered his wife and got away with it, but even that brief flashback is left purposefully ambiguous.

Aside from these two characters (and Margot Robbie as Sharon Tate, who has less to do but positively glows as a young actress still giddy at the idea of seeing herself on the big screen), Tarantino seems more interested in just feeling the aura of the late 1960s than he is in developing a tightly written ensemble of characters that we see in some of his other films. This is not a criticism, by the way, just an observation — if the vibe of 1960s Los Angeles were a character it would be fourth-billed, maybe even third depending on how good its agent was. The entire production feels a bit meandering and slow, but not purposeful in its slowness as we sometimes see in a film like Inglourious Basterds, where there’s a palpable tension slowly ratcheting up. No, Once Upon a Time in Hollywood is merely content to luxuriate in the richly developed world it has painstakingly brought to life. It’s not necessarily a problem, and in a lot of ways it adds to the film, but with a two hour and 45 minute run time it’s surely not unreasonable to suggest that it could have benefited from slightly tighter editing.

Overall, it’s a worthy addition to the Tarantino catalogue, featuring what could almost be mistaken for a rare bit of self-reflection on the part of the famously brusque director. It’s certainly the most wistful, almost melancholy, of his films, even if it does manage to fit in a bit of trademark ultra violence that feels jarring and perhaps even overly vicious, even by Tarantino standards. Great leading performances and wonderful chemistry between Leonardo DiCaprio and Brad Pitt elevate Once Upon a Time in Hollywood, creating a thoughtful, tantalizing glimpse at the Hollywood of yesteryear and what might have been.

Rating: ★★★★

Directed by: Quentin Tarantino
Written by: Quentin Tarantino
Cast: Leonardo DiCaprio, Brad Pitt, Margot Robbie, Margot Qualley, Timothy Olyphant