2020 Official Speakeasy Oscars Predictions

The Oscars are this Sunday. It’s Hollywood’s biggest night. I would know…I live right next to the Dolby Theater where they are held. And so I’m here to give you my official picks. Here are all of my picks and they can help you win some money. If you want to know why I say that, I only picked two wrong last year. But I’ll also breakdown Best Picture and the acting categories (which seem to be locks).

Best Picture

Pick: 1917

So why 1917? Simply put: It’s the best picture out of all the nominees. My personal favorite out of all of the nominees is JoJo Rabbit. But that’s one ting people forget about the “Best Picture” category: It’s not about your favorite film. It’s about the production and how it makes a film so good. While the other nominees have great stories, 1917 really does the best at putting everything together. From the action sequences to the one-shot feel of the film, the producers of the film really made you feel like you were in the trenches during this battle of World War I. If I had to pick a dark horse, it would be Parasite. Why? Simply put if you removed the subtitles from the film, you could still understand what was going on because of the visual cues and how the scenes were shot. But in the end, 1917 will likely win

Best Actor

Pick: Joaquin Phoenix, Joker

I’m going to keep this one brief. Joaquin Phoenix will win. He’s won every award this award season for his portrayal of the Joker in Joker. He’s always been an actor the turns into his character. But the recognition he’s received dates back to last summer in Cannes when Joker won the award for best film at the annual film festival. Simply put, there is no dark horse in this race. This is a lock if I’ve ever seen one

Best Actress

Pick: Renée Zellweger, Judy

So there’s something that the Academy and all other groups that do award shows love: Hollywood. Judy is a biopic of Hollywood starlet Judy Garland, who is famous for the roles of Dorothy in The Wizard of Oz, Meet Me in St. Louis, and the original A Star Is Born. Renée Zellweger is very much associated with the Oscars already and has won the award for “Best Supporting Actress” for her role in Cold Mountain back in 2004 and nominated two other times before this year. The Academy loved her then and loves her now. She’ll win her 2nd Oscar.

Best Supporting Actor

Pick: Brad Pitt, Once Upon A Time in Hollywood

Simply put, it’s Brad’s time. He’s been a Hollywood icon for years. He technically already has an Oscar for being a producer on 12 Years A Slave when it won “Best Picture” in 2014. But he’s been nominated three times for Best Actor/Supporting Actor and probably could have been nominated a few more times. But Once Upon A Time in Hollywood really was one of Pitt’s best roles. It helps being good friends with your co-star, Leonardo DiCaprio. Yet, you can tell that Quentin Tarantino wrote the part of Cliff Boon for Brad Pitt; and Brad Pitt knocked it out of the park!

Best Supporting Actress

Pick: Laura Dern, Marriage Story

Pretty much take what I said about Brad Pitt and replace his name with Laura Dern. While Netflix has won a couple of Oscars, this will be their big one and it couldn’t happen to a better person. We’ve had so many great films and shows with Laura Dern and she’s won so many awards in her career. But this is only her third Oscar nomination and probably should have been nominated for more in the past. It’s her time as well. Marriage Story is not an easy film to watch. But Dern really took in the role of being a divorce lawyer and made it her own. What we are left with from Marriage Story is the critical acclaim with the nominations (Scarlett Johannson and Adam Driver were both nominated for “Best Actress/Actor,” along with “Best Picture” for the film) and memes, which I’m sure you’ve seen. But Laura Dern is really who stands out in this film and she’ll finally get her Oscar for it.

Tune into the 92nd Academy Awards this Sunday LIVE at 8pm EST/5pm PST on ABC

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