Keith LaFountaine’s review published on Letterboxd:
The phrase "a love-letter to Hollywood" is perhaps one of the most overused. I'm guilty of using it, and many reviewers I respect have used it as well. Yet, the phrase seems to remark upon a specific type of nostalgia -- one steeped in cigarette smoke, old-school rock n' roll, and vibrant colors, all of which recall the Hollywood of yesteryear.
I suppose some folks may call Once Upon a Time In... Hollywood a love-letter to an era of cinema that is no longer: one that was littered with stars, which was vibrant and exciting, yet which was also changing drastically. As the Rick Dalton's of Los Angeles find themselves washed up, playing the antagonist opposite a newer, fresher face, Sharon Tate is looking up at the silver screen with wide-eyed, youthful excitement. She's breathless when she mentions that she's the star of a film, while Dalton is almost resigned to rattling off his resumé like he's a waiter listing the available specials.
In this way, I think Once Upon a Time In... Hollywood is the most personal film we've ever seen from Tarantino. While he's always been one to reference the films he loves, and while he's never been shy about acknowledging that his films often "borrow" from other films he's fond of, this is perhaps the only film in his canon that is truly personal and intimate. The sets are constructed with such lavish precision, it seems as though the theater screen works as a time machine to 1969. These characters are also treated with a certain level of respect, to a degree that many of his other characters are not. While Rick Dalton can be buffoonish and over the top, we do sympathize with his emotional situation. While Cliff Booth's past is defined by a single, despicable action (one that Tarantino never really returns to after introducing it), his interactions with Rick and his dog help humanize him. Sharon Tate doesn't get many lines in the film, but every scene she is in is colored by a youthful optimism and starry-eyed exuberance that helps make her character stand out. In essence, Sharon Tate is the soul of this film, just as Rick Dalton is the harbinger of the fading past.
This dichotomy is the central conflict of the film. While Sharon Tate exists on the perimeter of the film, weaving in and out of the narrative (as does Manson and his "family"), her looming tragedy is not what defines the story. Far from it, in fact.
Tarantino's indulgence in this film, and its personal connection to him, is further noticeable by its considerable length. He clearly loves these characters, and he enjoys sitting his viewer down with a couple of characters and allowing the ensuing conversation to follow a natural cadence. The runtime and pacing of this film are certainly what many people will have an issue with. Yet, Tarantino describes Hollywood as a "hangout movie" and I can see why -- he's not really concerned with cohesive plotting. It does exist, and I'm sure another viewing would lend itself to pointing out the specific roadmap Tarantino was following, but his concern is more with these characters. Therefore, he's not really worried about pacing, nor is he worried about plotting. That's almost admirable in a way, but it's something that audiences will certainly love or hate. For me, I will never mind just watching Tarantino's characters interact. While praise for his dialogue is almost a cliché to include in a review, it's true that he understands film dialogue in a way many other writers do not.
I know that many will feel underwhelmed by Hollywood, mainly because this is not the typical Tarantino affair. It feels almost lackadaisical and meandering when compared to the likes of Kill Bill and Django Unchained. Yet, I think this is also the most mature we've ever seen Tarantino. While he indulges in some grotesque imagery (because, of course, he's still Tarantino at the end of the day), the story he is telling feels more multifaceted than ever before. That's part of what helps cement it as a masterpiece for me.
Yet, the ironic silver lining to this entire film -- and one that is supremely dark -- is its title: Once Upon a Time... In Hollywood. At the end of the day, I think Tarantino is hinting that much of the story of Rick Dalton and Cliff Booth is a fantasy. It is fabricated by the same machine that the film is looking back on so fondly. And yet, in that fantasy, there are still nuggets of truth, neighbors to be met, and pasts to be reconciled with. Such is the nature of Hollywood.