Jeremy’s Tophunder №90: Once Upon a Time . . . In Hollywood

8 min readApr 18, 2020

Once Upon a Time In Hollywood has the strange honor of being the movie on my Tophunder list that I’ve seen the least. Maybe that makes sense, given that it was released less than a year ago, but when I finalized the order of the list a little over a month ago, it was a movie I had only seen once, in theaters. Every other movie on my list I’ve seen at least three times, several of them I’ve seen 20 times or more (hell, I saw The Dark Knight three times in theaters alone).

Seeing it once in theaters was enough to know that I liked the movie enough for it to make the list. I slid it in at №90, because it didn’t feel right to rank it super highly having seen it only once. As I re-watched it earlier this week, I realized, 90 is too low. I love this movie. If and when I make a new copy of my list, Once Upon A Time In Hollywood will be at least 30 or 40 spots higher.

(I’m going to talk a bit about the ending of the movie towards the end of this post. If you aren’t interested in having the ending spoiled for you, stop reading at the break.)

It’s not Quentin Tarantino’s tightest script — that would probably be Resevoir Dogs. It’s not his most eye-popping visual take — that’s probably Kill Bill. It’s not his most innovative storytelling — that would be Pulp Fiction. It’s not his most ambitious tightrope walk — that’s probably Django Unchained. And it’s not his best overall movie — I’d vote for Inglorious Basterds there. But what Once Upon In Hollywood does is blend a number of famous Tarantino tropes together such that it feels more like a Tarantino movie than anything he’s done since the 90s.

The movie bounces back and forth between a fascinating character study of Leonardo DiCaprio’s character and Brad Pitt’s character (and their friendship), and a gushing love letter to the golden age of Hollywood.

It’s that last component that keeps the movie interesting for me. It struggles with pacing, and it’s probably 20 minutes too long, but the scenes that don’t really contribute to the plot are scenes that really capture the tone and the feeling that Tarantino is trying to create. Here’s Brad Pitt just driving around Los Angeles. In fact, there’s probably 10 or 12 minutes of the movie that is just people in cars driving around with no dialogue of consequence. Tarantino spends a lot of time selling the idea that these are characters (mostly) just going about their everyday lives in Hollywood in 1969. This gets hammered home when you contrast Rick Dalton’s (Leo) storyline with Sharon Tate’s (Margot Robbie). Rick Dalton is a fictional actor who is doing his best to get through a tough moment in his career, whereas Sharon Tate, who in real-life 1969 is a few months away from being brutally murdered by members of the Manson Family, here just exists as a bubbly 26-year old actress having a good time. She goes to a party at the Playboy Mansion. She goes to buy a book for her husband. She stops at a movie theater to watch herself in The Wrecking Crew. The fake character is having a hard time. The real character is just having the time of her life.

During development to build buzz, Once Upon A Time In Hollywood was described as a Tarantino movie about the Manson Family murders, the same way that Inglorious Basterds was about World War II. That’s not really what the movie is at all. Members of the Manson Family appear intermittently, and the fictional DiCaprio/Pitt storyline weaves itself into the true Manson storyline to some extent, but for the most part, the Mansons are on the periphery. I was a little surprised by that the first time I saw it, but as I re-watched it, I was glad that they aren’t the focus.

The movie received some criticism for its portrayal of Sharon Tate. She has very few lines of dialogue, and ultimately, her presence in the movie doesn’t contribute to the plot in any meaningful way until the last 20 minutes of a 160-minute movie. To some extent, I think those are valid criticisms, but that’s not the way I see her role in the movie. The movie’s official website describes it as “multiple storylines in a modern fairy tale tribute to the final moments of Hollywood’s golden age.” It seems that Tarantino feels that the golden age of Hollywood ended the night Sharon Tate was murdered, which is a cut-off line that seems as reasonable to me as any other. If that’s the case, then it makes a lot of sense to me that the Tate parts of the movie are just getting to follow her around and spend time with her. It doesn’t matter that she’s not advancing the plot, that’s what the fictional storyline is for.

I found Robbie’s performance to be pretty strong as Tate, but it was clearly overshadowed by both DiCaprio and Pitt, who were each spectacular. DiCaprio hasn’t really played a down-on-his-luck sad sack before — he’s almost always the coolest guy in the room. His random speech impediment is fantastic, and his struggle to remember his lines is always just funny enough to keep a slow scene moving. Pitt was the high point of the movie for me — finally winning a long-deserved Oscar. A description of Pitt that I’ve always liked is that he’s a character actor trapped in the body of a leading man. Pitt has always had the ability to carry a movie on his own (like Moneyball or World War Z) and it usually turns out fine, but for my money, Pitt is at his best playing a weird character in an ensemble cast (Inglorious Basterds, Burn After Reading, Ocean’s) or as a sidekick to another great actor (Fight Club, Seven, here).

There are also a number of great Easter eggs hidden throughout the movie:

Brad Pitt’s car is a blue Volkswagen Karmann Ghia convertible, the same car that Uma Thurman drove in Kill Bill Vol. 2 (and according to a few sources, they used the same exact car).
Pitt’s character is rumored to have killed his wife. In a short flashback scene on a boat (which leaves the point ambiguous, but clearly hints one way), it’s revealed that her name was Natalie — a likely homage to Natalie Wood, who drowned under mysterious circumstances in 1981. Wood’s husband, Robert Wagner, was suspected but never charged in the case.
The book that Sharon Tate buys for her husband is Tess of the D’Urbervilles, which Roman Polanski would adapt into the movie Tess (1979) as a tribute to Tate.
Timothy Olyphant plays James Stacy, the real-life lead actor of Lancer. Olyphant is known for his portrayal of Western-esque lawmen in both Deadwood and Justified. In Olyphant’s final scene, he’s shown getting onto a motorcycle, a sad homage to Stacy’s motorcycle accident in 1973 that killed his passenger and left him disabled.
My personal favorite — one of the fake Spaghetti Westerns that Leo’s character stars in was directed by real-life director Antonio Margareti. That name, however, might be better known as one of the assumed names the Americans use to gain entrance to the premier of Nation’s Pride in Inglorious Basterds.

And then there’s the last 20 minutes.

The first time I saw the movie, I kept glancing at my watch.

Not because the movie was long and dragging (it’s long, but I didn’t mind), but because I was on edge. The longer the movie went, the more anxious I felt about watching what I assumed would be the climax or an otherwise pivotal moment in the movie — the members of the Manson Family brutally murdering Sharon Tate and the other people in the house on Cielo Drive.

It never occurred to me that Tarantino would provide a revisionist version of history, same as he did in Inglorious Basterds. The first two-plus hours felt so different from Basterds (in terms of how much of the movie was meant to feel real) that I just didn’t see it coming. I was expecting to see Tate get murdered, and I was expecting to feel really uncomfortable with it. Tarantino subverted that story rather beautifully with the idea to have the Manson Family call an audible at the last second and invade Leonardo DiCaprio’s house, and to have world-class stuntman/war hero Brad Pitt (and his trusty Pit Bull) save the day.

It’s classic Tarantino. The violence is gratuitous (even by Tarantino’s standards — I’m usually not turned off by it, but I had to watch through my fingers at a few points) but still manages to be surprisingly funny at times. The aftermath of the skirmish is heartfelt and cathartic. It leaves you in a slightly different mood than the ending of Basterds does. In Basterds, you get to witness the cathartic destruction of Hitler and the Nazi regime, and its satisfying, mostly because the Allies won the war anyway in real life. Tarantino took a win and made it more emphatic. The ending to Hollywood isn’t quite the same. After Brad Pitt leaves in the ambulance, assuring Leo that everything is okay, we see Leo walk up the driveway to Tate’s house for a drink, and we’re happy. But we have to confront the fact that this isn’t reality. Tate, three of her friends, and her unborn child were the victims of a brutal attack by a violent cult of psychopaths. It’s a much more melancholy feeling.

As I continue to re-watch Once Upon A Time In Hollywood over the years to come, I suspect it will catch up with the other Tarantino movies I have on my list (three of which crack the Top 40). Having seen it only once before finalizing my list, I didn’t want to accidentally put it too high. It turns out I put it too low. I’ll leave it at №90 for now — good enough to get in, good enough to climb higher, but with just two viewings over the last year, there just isn’t enough history and nostalgia attached to it yet to put it much higher. But I have a feeling it will find its way into the Top 50 at some point down the road.

(For a refresher on the project, I introduced it in a Facebook Post on Day 1)

Here’s our progress on the list so far:

6. The Fugitive

7. The Dark Knight

9. Saving Private Ryan

11. The Big Short

13. Lord of the Rings: The Fellowship of the Ring

17. Ocean’s 11

18. Air Force One

21. The Other Guys

22. Remember The Titans

24. Apollo 13