2019 was a great year for film. It gave us "Parasite," "Marriage Story," "Jojo Rabbit" and "Little Women," among others. And while I wanted either of the first two to win Best Picture, I was almost certain that the Oscar would go to "Once Upon a Time… in Hollywood" — not because it was the best film of the year, but because I (thought) I knew a thing or two about the academy.
Best Picture has always been a wildcard. Not only does it have adifferent voting system than the other categories (i.e., preferential balloting), but it also allows all members of the academy to vote, unlike specific categories such as Best Director or Best Editing. In other words, you don’t have to be an acclaimed director to vote for Best Picture.
As a result, Best Picture is often awarded to the most politically relevant and popular film of the year — not necessarily the best. This is why we occasionally get Best Picture winners like "Green Book" (2018) and “Crash” (2004). It’s also worth noting that people love watching themselves on the screen, especially those who work in Hollywood. That’s why films like "La La Land" (2016) and "Mank" (2020) score countless nominations, despite their arguably mediocre subject matter.
This is where "Once Upon a Time... in Hollywood" comes in. Was it the most critically acclaimed film of the year? No. A lot of people liked the film, but not as much as other nominees. But like I said, universal likeability doesn’t matter here because, at the end of the day, it’s Hollywood people who get to pick the winner — not average Joes. Considering that the title of this movie has “Hollywood” in it, I was pretty confident that it would take home the Oscar.
I should also mention that the Oscars love films that feel like old-school Hollywood. "Green Book," despite not being a great film, felt like an old-school Hollywood road-trip film. The same can be said about "The Shape of Water" (2017), which brought a modern twist to old-school romance.
"Once Upon a Time… in Hollywood" was the most old-school Hollywood film of the bunch. For a lot of people who work and live in LA, this film served as a nostalgia trip that accurately captured the energy of the city. Sure, the runtime was long and the first two acts were slow, but when you’re watching the place you’re from on the big screen, you don’t really care.
Finally, despite creating some of the best films of all time, a Quentin Tarantino film has never won Best Picture. He’s long overdue, and all of Hollywood knows it. Did I think this was the first film he should've won for? Absolutely not. But it would’ve made a lot of sense. "Once Upon a Time... in Hollywood" felt like a culmination of his career.
All and all, "Once Upon a Time… in Hollywood" has this quality where it will make a good amount of people happy and a good amount of people pissed. Considering that it was Tarantino’s (perhaps last) love letter to Hollywood, it should’ve won the Oscar for Best Picture.