The protagonist among the three characters is Rick Dalton (Leonardo DiCaprio), an actor whose concerned about the state of his career given that his most recent acting gigs have been guest spots as bad guys in TV shows. Where exactly could his career go from here? Well, wherever he goes, his stuntman best buddy/personal chauffeur Cliff Booth (Brad Pitt) will be right there with him. Dalton and Booth are an inseparable bunch as they navigate a Hollywood that's being turned even more upside down than Dalton's career prospects. Oh, and who is that as Dalton's next-door neighbor? Why none other than our third lead character, Sharon Tate (Margot Robbie)!
Once Upon a Time in Hollywood isn't just Tarantino crafting a homage to an era of Hollywood history, he's practically created a shrine to it. This means this period-era setting is realized in painstakingly detailed production design, costumes and props that make you feel like you've truly been transported to 1969 Hollywood (watching it projected in 35mm also helps add to this effect). The soundtrack also does its part in helping to sell the 1969 setting by peppering numerous scenes with head-bopping tunes straights from this era and, thankfully, avoids the various songs that have been overplayed in other 1960s songs (no Fortunate Son to be found here).
As for how the story of Once Upon a Time in Hollywood itself handles its 1969 setting, that's where the film gets more mixed results. Specifically, Once Upon a Time in Hollywood frequently runs into trouble of being exclusively a lot of references to 1969 pop culture without having much else on its mind. Tarantino has always referenced elements of past pop culture in explicit terms in his work but usually, it emerges in a way, that can still work even if you're not familiar with the reference in question.like the use of a portion of the Ironside theme song in the Kill Bill movies, Here in Once Upon a Time in Hollywood, if you haven't rehearsed every TV Guide listing from 1969 like Tarantino has, there's not much else to enjoy in prolonged conversations concerned with just prattling off titles of TV shows from this era. Even as a pop culture junkie, I kept wishing there was more meat on the bones of these extended conversations beyond just name-dropping pop culture artifacts relevant to the late 1960s.
This is especially an issue since Hollywood is adhering to the slow-burn approach of Tarantino's best movie, Jackie Brown. For this particular take on that approach, much of the runtime is dedicated to a hangout aesthetic even though too many of the characters are just one-scene celebrity cameos rather than entertaining personalities you can enjoy hanging out with. In its most meandering moments, Hollywood is like watching Tarantino romping around in a theme park with glee in the distance while you're watching from afar behind a chain-link fence, wishing you could get closer to what's on the horizon. In other words, you totally get that Tarantino loves this setting but the movie doesn't make a great case for getting a viewer to understand why he loves it.
Thankfully, there's more going on here in Once Upon a Time in Hollywood than Tarantino flexing his encyclopedic knowledge of cinema. For one thing, the best melancholy moments of the production derived from Dalton and Booth going through personal upheavals just as the American film industry goes through its own disruption are the best use of the period-era setting in the entire screenplay. are the scripts. Tarantino's ability as a screenwriter to pen instantly memorable humorous dialogue is also alive-and-well here, particularly in any of the lines said by an adolescent co-star Rick Dalton works with on the set of a Western TV show or the comedy given to Brad Pitt, who emerges as the shining star of the expansive cast of Once Upon a Time in Hollywood.
Giving his best performance in years, Pitt's style of laidback comedy turns out to be a perfect fit for the similarly nonchalant vibe of Once Upon a Time in Hollywood. Pitt had me cackling so often with just the tiniest bits of casual comedic business. Also delivering a memorable turn is Leonardo DiCaprio in the comically sad-sack mode that he seems to excel the most at (remember how well he did physical comedy in that one scene in Wolf of Wall Street?) DiCaprio's intensity as an actor in dramatic works like The Revenant is honestly even better in comedy where it can be used to have schlubby characters make mountains out of molehills, like in a hysterical scene here where Dalton berates himself for messing up his lines in a scene.
Margot Robbie is also around in the third lead role to play Sharon Tate and her immensely compelling and endearing performance helps to compensate for how the character is more of a symbol rather than a fully-formed human being in their own right. With a trio of entertaining lead performances like these plus impressive visual recreations of Hollywood circa. 1969, Once Upon a Time in Hollywood ends up being satisfactory, though overlong, cinema. However, this may just be the Tarantino movie that struggles the most with making sure it has something more to offer than just a heap of references to past pop culture. In his prior works, influences of the past drove Tarantino to make fresh storytelling like Death Proof and Jackie Brown. Here in Once Upon a Time in Hollywood, the storytelling is mostly about reminding viewers that F.B.I. and The Man From U.N.C.L.E. simply existed and that makes for a less enjoyable and more insular experience among his directorial works.
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