Once Upon A Time In Hollywood: Predicting Its Oscar Chances

It may have taken seven months, but the film community has its first serious Oscar contender with Quentin Tarantino’s Once Upon a Time in Hollywood. Tarantino’s tribute to the end of the Golden Age in Hollywood has been rumored to be in the Oscar race ever since the film was announced two years ago. Once Leonardo DiCaprio, Brad Pitt, and the prolific ensemble cast were officially announced, the Best Picture hype began to build.

*This article will contain light spoilers.*

Once Upon a Time in Hollywood revolves around the friendship between an aging actor, Rick Dalton (Leonardo DiCaprio), and his stuntman, Cliff Booth (Brad Pitt), in 1969 Los Angeles. The film industry is changing and Dalton and Booth both struggle to adapt to the new times. While this is going on, the major subplot of the film involves Sharon Tate (Margot Robbie), Dalton’s next-door neighbor, and the Manson family and their interactions leading up August 9, 1969, when members of the Manson family murdered Tate and her guests at Tate’s house.

All of Tarantinos’ films include his signature style of extended dialogue sequences, large ensembles, and brutal depictions of violence. Those elements were on full display in Once Upon a Time in Hollywood. However, this film will go down as Tarantino’s most nostalgic and tender film to date. This film is a love letter to the Golden Age of Hollywood. From recreating Hollywood Blvd to the music, clothing, and stars, Tarantino’s Once Upon a Time in Hollywood is as accurate a description of 1969 LA as you’ll ever see on film.

Due to Tarantino’s reputation and a star-studded cast which included DiCaprio, Pitt, and Robbie, Once Upon a Time in Hollywood debuted to $40.3 million at the box office, marking the largest opening of the director’s career. The film has also been well-received from critics with an 84% on Rotten Tomatoes. Now, attention will turn to the 2020 Oscars. The question is not if Once Upon a Time in Hollywood will be nominated for Oscars, but how many Oscar nominations will it receive? Let’s break it down by category.

Best Picture – Yes

There is nothing that the Academy loves more than a film about Hollywood. A film that showcases Hollywood and all it has to offer is a lock for nominations. Add in the fact that it’s a Tarantino film and has “movie stars” in every sense of the word means Once Upon a Time in Hollywood will be in the running for multiple Oscars. For example, take La La Land as another film that highlights Los Angeles. Damien Chazelle’s musical received a record-tying fourteen nominations, winning six categories. Once Upon a Time in Hollywood may not receive that many nominations, but Best Picture is just the first of many nominations.

Best Actor for Leonardo DiCaprio – Yes

In his first film since his Oscar-winning performance in The Revenant, DiCaprio is at his best once again in Once Upon a Time in Hollywood. The way DiCaprio is able to channel an aging star with such intimacy and care is amazing to witness. It’s a sentimental and loving side of DiCaprio we haven’t seen in years. Add Once Upon a Time in Hollywood to his long list of excellent performances.

Best Supporting Actor for Brad Pitt – Yes

Pitt did not have as much screen time or lines as DiCaprio so Sony is most likely going to position Pitt as a supporting actor. That being said, Pitt and DiCaprio have tremendous chemistry. Pitt’s cool, no-nonsense persona blended perfectly with Dalton’s egotistical and conceited mannerisms. Essentially, Pitt was his Rusty character in the Ocean Eleven series. Keep in mind that Pitt is going to push for Best Actor for his performance in Ad Astra, which comes out in September. Could Pitt be a double nominee come Oscar night?

Best Supporting Actress for Margot Robbie – No

This is tricky. I thought Robbie did a solid job with the material she was given. Robbie depicted Sharon Tate as this beautiful, star-in-the-making who was married to one of the hottest directors in Hollywood, Roman Polanski. We know what happens to Tate in real life so it’s hard to watch her onscreen and not think ahead to her encounter with the Manson family. Robbie also does not have many lines. My gut says she won’t receive a nomination, but if Once Upon a Time in Hollywood dominates major categories in award shows prior to the Oscars, I won’t be surprised if the momentum leads to a nomination for Robbie.

Best Director And Best Orginal Screenplay for Quentin Tarantino – Yes

If I had to say which category Tarantino has a better shot in receiving an Oscar nomination, Best Orginal Screenplay over Best Director is the better bet. Tarantino received screenplay nominations for Inglourious Basterds, Pulp Fiction, and Django Unchained, winning for the last two in that list. On the flip side, Tarantino has been nominated twice for Best Director: Pulp Fiction and Django Unchained. Tarantino’s revisionist history in the final act may rub some voters the wrong way, but it shouldn’t stop him from receiving a nomination for screenplay. This should also lead to a directing nomination as well because as I’ve previously stated, this is a softer, more contained version of Tarantino in his homage to 1969 Hollywood. Voters will reward his nostalgic vision.

Other Categories Where Once Upon a Time in Hollywood Will Receive Nominations

• Cinematography
• Production Design
• Film Editing
• Costume Design

If these predictions turn out to be true, Once Upon a Time in Hollywood will receive at least nine Oscar nominations, which would be a career-high for a Tarantino film. It’s not out of the question that the film will receive less than nine or more than nine nominations. However, don’t expect this film to ride off into the Hollywood sunset. Quentin Tarantino’s Once Upon a Time in Hollywood will be a major player in the Oscar race.