Review: Quentin Tarantino’s Once Upon a Time…in Hollywood Revisits, Celebrates a Bygone Cinematic Era

Like many works by Quentin Tarantino, Once Upon a Time…in Hollywood is an exercise in creation and re-creation, often simultaneously, but never more so than in this love letter/death knell to an era of Hollywood that was ushered out in the late 1960s by films like Easy Rider and the cheaply made but highly influential spaghetti westerns of Sergio Leone.

Once Upon a Time in Hollywood Image courtesy of Columbia Pictures

Within this very real backdrop of 1969 Los Angeles, we meet Rick Dalton (Leonardo DiCaprio), who had a long, successful run on the black-and-white TV Western “Bounty Law” in the late ’50s and early ’60s. He was just a big enough star to endorse products (be sure to stick around during the credits for one of his commercials for a familiar cigarette brand) and even top line a few noteworthy motion pictures (people seem partial to one called Fourteen Fists of McCluskey). But by the time 1969 rolls around, his movie parts have dried up and he’s been reduced to one-off parts (almost always playing the bad guy) on TV shows.

His constant companion is his stunt double Cliff Booth (Brad Pitt), who himself has been reduced in stature, now taking on the role of chauffeur to Rick, since Rick racked up too many DUIs to keep his license. Cliff hasn’t done much serious stunt work in quite some time, but hangs around Rick when he’s on set somewhere, hoping to get pick-up work. But Cliff has a checkered past, including a short fuse and a long-held legend that he killed his wife and got away with it There’s a fantastic sequence involving him picking a fight with Bruce Lee (Mike Moh) on the set of “Green Hornet,” that is one of those perfect Tarantino moments that doesn’t really move the plot forward at all but gives us so much detail about a character (in this case Cliff) that it becomes indispensable.

Rick and Cliff are drinking buddies, best friends and patient/therapist, and they seem to do nearly everything together, usually landing at Rick’s house to drink and watch TV into the wee hours. It just so happens that this actor on the way down lives right next door in the Hollywood Hills to a filmmaker on the way up, Polish-born Roman Polanski and his actress wife Sharon Tate (Margot Robbie). As the film opens, it’s only been about six months since Polanski hit the big time in America with Rosemary’s Baby, and in many ways his opulent and decadent lifestyle are exactly the sort of force that push performers like Rick out of business.

Although Rick and Sharon (Polanski himself is little more than a glimpsed specter of a presence) live mere feet apart, their paths don’t cross for nearly the entire film. And that’s because Once Upon A Time…in Hollywood isn’t about the intersection of these two lives—one of which is real and well known, one of which is fictional. It’s about how their lives diverge because of the eras from which they arose. As much as many may think Robbie’s lack of substantial storyline is detrimental to her, I believe what Tarantino is attempting to do with the Sharon Tate character is something that few do today, which is bring her to life, instead of focusing on how she was brutally murdered by members of the Manson Family on August 9, 1969 (not coincidentally the date of the final sequence of this movie).

Tarantino isn’t attempting to imply that Tate’s career was something special, but he very much wants us to understand that the Valley of the Dolls star was. She is portrayed as a loving, open-minded, and kind person, who still appreciated every time she was able to star in anything. In the case of this film, she talks her way into an afternoon screening of her latest work, The Wrecking Crew, just to see if the audience finds her performance funny (they do). And you can’t help but find her response to their laughter delightful and endearing. She’s still friendly with an ex-fiancee, hair stylist Jay Sebring (Emile Hirsch), who she hangs out with all the time at her home, but she also likes to go to parties at the Playboy Mansion with her husband and friends like Steve McQueen (a dead-on cameo by Damian Lewis).

Perhaps more than any other Tarantino film, Once Upon a Time… gives us visual and auditory sensory overload—in the background of every scene, you can see period movie ads, marquees, billboards, cars, etc. But the film's soundtrack is an almost hypnotic mix of ’60s music, radio commercials and fuzzy DJs with old school radio announcer voices that you can sometimes understand, but not always. Instead of simply paying tribute to favorite filmmakers, movies or composers, Tarantino has created a pastiche of a generation and specific place that devoted itself to creating entertainment, for better or worse. The film also gives the director a chance to show off his knowledge of older television and its singular style, from the theme songs and open credits to the choppy dialogue and recycled plots and characters. And while it sounds like you’ll need a film/TV history degree just to buy a ticket, most of these details work just as well as background in setting the period, but if you choose to, you could drive yourself crazy noticing the details that are on screen for only seconds.

Once Upon a Time…in Hollywood is a film less about story and more about its inevitable conclusion. Each leading actor gets at least one great moment. Pitt’s comes when he travels to an old ranch where he used to shoot in the company of a young woman (likely underage) named Pussycat (a wonderfully edgy Margaret Qualley). The ranch has since been overrun by hippies, mostly women, and it turns out this is the home of the Manson Family, including Squeaky Fromme (Dakota Fanning). Much like Polanski, Manson (Damon Herriman) is barely seen, and it becomes clear that the film is about those on the periphery of fame (which is the bulk of Hollywood) rather than the select few who make it big.

An extended piece of the film is devoted to Rick shooting a Western pilot opposite rising star James Stacy (Timothy Olyphant). It’s an incredible moment to get to watch DiCaprio work through the scene as another actor. It turns out Rick has a slight stutter, but not when he’s acting. In his mind, he conquers all in front of the camera, and becoming someone else means losing the weaknesses of his true self. The sequence all leads to a wonderfully dramatic kidnap scene in the show that is likely far better acted than most things on TV at the time.

The film follows Rick and Cliff when Rick gets a chance to make a series of Italian Westerns, but the story only lingers long enough in Italy for two things to happen: Rick picks up an Italian wife (Lorenza Izzo) and decides he can’t afford to keep Cliff on as a driver any longer. I won’t say how the film ends, but it does involve Rick and Cliff getting drunk off their heads to celebrate the end of an era, and an incident that occurred on the same street that Rick lives on that also marked the end of an era in Hollywood.

I feel like I’ve barely scratched the surface of the many familiar faces featured in Once Upon A Time…, including the final on-screen appearance of Luke Perry, as well as Al Pacino, Kurt Russell, Zoe Bell (who is also the film’s stunt coordinator), Bruce Dern, Lena Dunham, and so many more. It’s a movie that mourns and celebrates a time and place, and with the help of Tarantino’s regular cinematographer Robert Richardson (shooting on film), it looks like a film from that period as well. The film is a glorious gift to movie lovers and history lesson of sorts to those who only dabble in the cinema arts from time to time. However you approach it, it’s one of Tarantino’s finest, most mature works, and I’m desperate to watch it again.

The film opens this Thursday night throughout Chicago; Music Box Theatre is one of only five venues in the world screening it in 70mm for a limited engagement.

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Steve Prokopy

Steve Prokopy is chief film critic for the Chicago-based arts outlet Third Coast Review. For nearly 20 years, he was the Chicago editor for Ain’t It Cool News, where he contributed film reviews and filmmaker/actor interviews under the name “Capone.” Currently, he’s a frequent contributor at /Film ( and Backstory Magazine. He is also the public relations director for Chicago's independently owned Music Box Theatre, and holds the position of Vice President for the Chicago Film Critics Association. In addition, he is a programmer for the Chicago Critics Film Festival, which has been one of the city's most anticipated festivals since 2013.