Jordan Canahai’s review published on Letterboxd:
Every film by Quentin Tarantino is, in some way or another, a love letter to the movies. And yet, his ninth feature (and if he's to be believed about his impending retirement, one of his last) Once Upon a Time In Hollywood, is perhaps the most personal ode to his love for cinema yet. Set in Hollywood in the late 60s (or more accurately Tarantino's dreamy vision of Hollywood in the late 60s), the film feels, in every frame, like it sprung forth directly from Tarantino's now decades-spanning obsession with Hollywood cinema, in particular the gritty genre films of the 1960s. Tarantino was, after all, born at the beginning of that most tumultuous decade, and some of his earliest movie memories involve going to the theater with his mom. There's a scene in Once Upon a Time in Hollywood where Sharon Tate (Margot Robbie) decides to pop into a matinee screening of her 1969 caper The Wrecking Crew, and while Tate lights up with joy watching her performance in a crowded theater as patrons laugh along with her, I couldn't help but imagine a young Quentin and his mom might be in the theater, as well.
There's something else about Once Upon a Time in Hollywood that makes it feel very personal, however, and it's when you consider the parallels between the middle-aged Tarantino in the twilight of his directorial career and the film's protagonist, Rick Dalton (Leonardo DiCaprio). Dalton was a once-prominent star of Western serials on television and other popular B-movie shoot-em-ups, but he now finds himself something of a has-been in Hollywood, typecast playing familiar roles with diminishing returns. When a slick producer (Al Pacino) suggests to Rick he accept an offer to travel to Rome and film Italian (or "Eye-talian", as Rick says) spaghetti westerns instead of floundering in Hollywood, Rick almost has a public meltdown. Just about his only friend is his longtime stunt double Cliff Booth (Brad Pitt), who serves as his confidant and chauffer, spending more time at Rick's fancy Hollywood pad than his own dingy trailer where he lives with his pit bull named Brandy. Both men drink too much, smoke too much, and have had their run-ins with the law in the past. Rick's new neighbors, he learns, are a young couple who are also in show business; the actress and model Sharon Tate, and her new husband, a polish director you may have heard of by the name of Roman Polanski.
Despite whatever his limitations as an actor may be, however, it's clear that Rick is a man possessed by his art, and is desperate to prove to Hollywood his best work has yet to be done. Some of the strongest moments in Once Upon a Time in Hollywood detail Rick's experiences on the set of a western he's been cast in as the bad guy. During filming he stumbles over lines, throws tantrums in his trailer, and even opens up to an adolescent co-star in a surprisingly moving moment, before finally nailing the take. Meanwhile, Cliff spends most of the picture driving nonchalantly from one spot in town to the next, making eyes at pretty hippie girls and handling any errands and odd-jobs for his client that come up. When the plot does lead him unexpectedly to a secluded part of town where he finds himself surrounded by the Manson family the scene is an unusually tense one that Tarantino draws the utmost suspense from, but the resolution is not what you expect. Pitt seems to relish the opportunity to indulge every macho instinct embodied by leading men of the 60s, turning Cliff into an individual whose manliness and devil may care bravado is so over-the-top he actually engages with Bruce Lee in hand-to-hand combat as a lark. Tarantino's dialogue also shines in the scenes where Cliff and Rick share the screen together. The character's friendship is at the heart of the movie, and both Pitt and DiCaprio have a macho rapport that suggests years of camaraderie. The actor's chemistry reminded me a bit of Clint Eastwood and Jeff Bridges in Michael Cimino's 1974 buddy caper Thunderbolt and Lightfoot.
Similar to how 2016's Hail, Caesar! saw Joel and Ethan Coen both sending up and paying tribute to Hollywood films of the 1950s, Once Upon a Time in Hollywood is chock-full of nods to Tarantino's favorite films of the 60s. For example, in one scene Rick relates to a co-star how he was considered for the role of Steve McQueen in The Great Escape, which Tarantino is able to realize replacing McQueen with DiCaprio in a famous scene from that film (Leo also does a pretty good Steve McQueen, it must be said.) There are also no shortage of nods and callbacks to Tarantino's own filmography, such as a movie-within-a-movie in which Rick brandishes a flamethrower to bring about the fiery demise of Nazi's recalling QT's World War II film Inglorious Basterds. Once Upon a Time in Hollywood also brings to mind P. T. Anderson's Inherent Vice from 2014 in its depiction of the seedier side of Los Angeles and its counterculture in the aftermath of the Summer of Love; when the good trip started to go real bad for some. This is by far Tarantino's loosest film to date, the hangout movie vibes of Jackie Brown and Death Proof are present throughout. It's probably safe to say Once Upon a Time in Hollywood is overly-indulgent and arguably overstuffed, but the film is never anything less than compelling and watchable, unlike The Hateful Eight which I found to be a disappointingly unpleasant bore. I would've liked to have seen more of Margot Robbie as Sharon Tate (her lack of screen time and spoken lines, especially compared to her male co-stars, has been a point of controversy since the film premiered to a great ovation at Cannes), but she owns the screen for the brief stretches when she is the focus. In true Tarantino fashion the soundtrack is also peppered with period-specific hits perfectly suited to the tone and rhythm of scenes. I especially liked his use of The Rolling Stones late in the film and a haunting cover of California Dreamin by Jose Feliciano.
And yet, while Tarantino obviously had a blast behind the camera, almost checking off his numerous cinematic influences one after another from each set piece to the next, there's an underlying sadness to much of Once Upon a Time in Hollywood that is appropriately suited to the themes of loss and failure at the heart of the picture, and especially when one considers the real-life tragedy that served as the inspiration. The ending of the film, especially in its sudden spurts of violence (not unexpected for a Tarantino film), is likely to be polarizing to some, but as a mediation on a bygone era, as well as a snapshot of a time when both Hollywood and America were in the midst of massive upheaval, Once Upon a Time in Hollywood may well stand as one of Tarantino's most interesting pictures to date.