Jacob Gehman’s review published on Letterboxd:
So, Once Upon a Time in Hollywood feels like the sort of film that could gain a lot on a second viewing. I spent a lot of the first hour or feeling like I was floundering; between a mixture of characters, scenes that feel isolated without informing a larger plot arc, and bouncing between the film world's present day and clips from Rick Dalton's filmography.
Rick Dalton is an actor, namely in low rent Westerns, but his career is starting to flounder a bit. His two friends are Cliff Booth (his stunt double) and alcohol. His roles are becoming more and more limited, and the roles he does get are unfulfilling and done hungover. Meanwhile, Cliff is less a stunt double and more Rick's personal assistant. His reputation keeps him off many sets, so when a cute girl requests a ride, who is he to turn her down?
In a career built upon referential cinema, Once Upon a Time in Hollywood may just be Tarantino's most referential film. He assigned ten films for interested viewers to watch before seeing Once Upon a Time; he wants people to have the tools in their belt to properly appreciate the film. (haha, I didn't watch those films.) Not to mention a lot of the characters in the film are (or were) real people: Roman Polanski, Sharon Tate, Bruce Lee, Steve McQueen.
Without having "studied" before hand, I found myself spending a large portion of the film trying to remember my Polanski/Stone/Manson history--all people/subjects I've procured bits and pieces of knowledge about over the years, but not enough so to ever feel adequately up to speed on why all of these subjects were being brought together. Afterward I pulled up Tate on Wikipedia and all it took was the third paragraph of the opening blurb: "On January 20, 1968, Tate married Roman Polanski, her director and co-star in 1967's The Fearless Vampire Killers. On August 9, 1969, Tate and four others were murdered by members of the Manson Family in the home she shared with Polanski." Well, there you have it.
The loopy approach to telling the story, where a lot of focus is on building the characters rather than plot, does risk making the film drag as it spins its wheels with typical Tarantino dialogue flair and style without an apparent plot urging it along. Luckily, Tarantino constantly delivers entertaining scenes. I was never bored; even aimless Tarantino scenes go down smooth.
Of course, smooth doesn't always equate necessary, and there are a number of scenes Tarantino should have shortened or eliminated in order to trim the length down. This runs two hours and forty minutes--a long, flashy film that could have been a more satisfying, snappy experience. Margot Robbie as Sharon Tate gets third billing here, owning a fair number of scenes where she's the primary character. However, she almost never shares the screen with Leonardo DiCaprio and Brad Pitt (who play Rick and Cliff), making her feel like a third wheel in the film--a metaphorical younger girl in the back seat while her older sister makes out with a boyfriend--and her scenes feel like an afterthought. I suspect her screen time is mostly demanded by Tarantino's interest in adhering to history; he envisioned this odd alternative take on Manson murders, so Tate's presence is demanded. OK, sure. Look, I like some of her scenes, but they're always jarring because they're just rare enough that I'd forgotten about her by the time the script remembers to return to her. Each requires a certain amount of reorientation by the viewer to come to terms with. And the only thing they add (aside from more chances for Tarantino to put bare feet on the screen--both Robbie's and Margaret Qualley are given ample tootsie time) is texture for a secondary character.
While Tate is the easily identified time drain on the film, in general Tarantino's philosophy with Once Upon a Time in Hollywood seems to be: why make one scene, when you can make one scene twice as long at twice the cost! The reason longer runtimes on films like Inglourious Basterds and Pulp Fiction and Django Unchained work is that a focus on plot is adhered to and developed.
I'll be curious to see how a second viewing goes down. This feels like a film where the first half might gain a lot of potency the second time through. If the first half gets bolstered, that rating could easily rise. On a first watch, though, it's mid-tier Tarantino: constantly entertaining, but unfocused and much too long.