RANKING Who Will Win the Oscars, and Who SHOULD Win

By | February 5, 2020

Who Will Win Best Actor…

5. Jonathan Pryce, “The Two Popes”…I’m sure he’s just thrilled to be nominated, and he should be considering this should’ve gone to Eddie Murphy, Adam Sandler, or Christian Bale

4. Antonio Banderas, “Pain and Glory”…This film has a lot of people who absolutely love it, but I’m not sure a lot of Academy voters have even seen this movie, unlike the top three contenders.

3. Leonardo DiCaprio, “Once Upon a Time in Hollywood”…He’d have a lot better chance if he hadn’t won recently for “The Revenant,” and he wasn’t in a category of people who have never won before. Plus, his “Once” co-star Pitt is all but certain to win, and people may feel that’s enough for “Hollywood.”

2. Adam Driver, “Marriage Story”…People like him in this and another 2019 movie (“The Report”), but he’ll just have to wait his turn…

Winner: Joaquin Phoenix, “Joker”…Believe it or not, Phoenix has never won before (nominated for “Gladiator,” “Walk the Line,” and “The Master”), and even if he may be a pain in the ass, he’s been too good for too long not to win in a relatively weak category. This is also who should win, Phoenix is just too memorable, too alive to lose out to any of the listed performances here (although I did enjoy DiCaprio’s vulnerable, insecure actor portrayal, the first time the anxiety has really seeped through for him).

Who Should’ve Been Nominated: Although I do believe Phoenix caught a lucky break by Eddie Murphy, Adam Sandler, Christian Bale, and even Brad Pitt (for “Ad Astra”) not being nominated.

Who Will Win Best Actress…

5. Cynthia Erivo, “Harriet”…Best Actress is historically the least diverse acting category for the Oscars, as Halle Berry remains the only black woman to ever win, and all the nominees were white for the last several years.

4. Charlize Theron, “Bombshell”…Some people would probably say her dead-on Megyn Kelly portrayal should be ranked higher, and is the only legitimate threat to Zellweger’s dominance, but the movie didn’t do well at the box office, and I just don’t think a lot of Academy voters are wanting to reward a sympathetic portrayal of a major Republican. Plus, I believe voters may be more likely to vote for Margot Robbie in the supporting category if they really want to honor a “Bombshell” performance.

3. Scarlett Johansson, “Marriage Story”…Like Phoenix, Johansson has also never won, and actually never even been nominated before this year (snubbed for “Lost in Translation,” and “Match Point”) where she’s nominated twice. This seems like her better bet for a win, and the film is certainly widely seen (nominated for Best Picture)–but most seem to think it’s more Driver’s movie than hers.

2. Saoirse Ronan, “Little Women”…Unlike Johansson, there’s ample evidence that the Academy likes Ronan (she’s been nominated for “Atonement,” “Brooklyn,” and “Ladybird”), and it’s unusual someone would’ve been nominated 4 times when they’re only 25 and never won. If the Academy weren’t hell-bent on rewarding Zellweger’s slightly fuzzy, vague performance as Judy Garland, I’d say Ronan would easily be the favorite.

Winner: Renee Zellweger, “Judy”…There just doesn’t seem to be any way to prevent this from happening, even if Zellweger doesn’t really dig deep enough to let you inside her portrayal, and always seems a bit out-of-focus.

Who Should Win: Saoirse Ronan, although I have no doubt she’ll eventually win, why not reward her this year? “Little Women,” is a big-hearted, traditional Oscar movie so warm and cozy, it’s practically a blanket, and Ronan is the best performance in it. Both “Judy” and “Little Women” are old-fashioned and traditional, but only one is well-made. [And unfortunately I haven’t seen “Harriet,” but Theron was also excellent in “Bombshell.”]

Who Should’ve Been Nominated: I would’ve loved to have seen Jesse Buckley (“Wild Rose”), Tessa Thompson (“Little Woods”), Elizabeth Moss (“Her Smell”), and Meryl Streep (“The Laundromat,” her most experimental performance in years) nominated, even though I didn’t really expect them to be.

Who Will Win Best Supporting Actor…

5. Anthony Hopkins, “The Two Popes”…He’s very, very lucky just to be nominated. And given that “Popes” is generating the excitement of a wet fart with audiences, and Hopkins isn’t even campaigning, I wonder if Oscar voters wish they’d nominated Jamie Foxx (“Just Mercy”) instead.

4. Tom Hanks, “It’s a Beautiful Day in the Neighborhood”…Hanks may also be thanking his lucky stars he didn’t get snubbed again. Somehow, one of the only actors ever to win Best Actor two years in a row (“Philadelphia,” “Forrest Gump”) hasn’t been nominated in nearly 20 years, and has been snubbed many times in that period (“Sully,” “Captain Phillips,” “The Post,” “Saving Mr. Banks,” and my favorite “Road to Peredition” were all prognosticated to net him a nomination).

2. [Tie] Joe Pesci “The Irishman,” and Al Pacino “The Irishman”…The fact that I can’t decide which has the better chance (Pesci is more critically acclaimed, Pacino is more the heart of the movie) should tell you why neither one has a great shot at upsetting Brad Pitt. Even if they weren’t there splitting votes for each other, “Irishman”‘s momentum seems to have passed, and both actors have won before.

Winner: Brad Pitt, “Once Upon a Time in Hollywood”…Despite three previous nominations as an actor (“12 Monkeys,” “Benjamin Button,” and “Moneyball”), Pitt has never won as an actor (he won as producer of “12 Years a Slave”) unlike every one else in this category. Sunday night looks to remedy that. Pitt’s won every pre-Oscars indicator, he’s universally well-liked (unlike Phoenix), and has given gracious acceptance speeches (also unlike Phoenix). Also, “Once” is nominated in many major categories (Best Picture, Best Director, Best Screenplay, Best Actor) and this seems like its best chance of a win. Everything is going in his direction to the point I would bet money on it, and say this is easily the safest prediction of the major categories.

Pitt also should win even though I enjoyed Pesci and Pacino in “The Irishman.” But Pitt’s Cliff Booth is just too iconic, too cool, too relaxed and enjoyable–it’s a textbook case of an actor perfectly aligning with a role.

Who Should’ve Been Nominated: Although I would’ve loved to have seen Kelvin Harrison (“Waves”), Shia LeBeouf (“Honeyboy”), and Tommy Lee Jones (“Ad Astra”) be nominated, the only snub in this category that really and truly kills me is Willem Dafoe in “The Lighthouse,” probably my favorite performance from an actor this year. It is a class in great acting, and a Goddamn, crying-out-loud shame the Academy decided to go with Hopkins instead.

Who Will Win Best Supporting Actress…

5. Kathy Bates, “Richard Jewell”…Bates has won this category before (she’s the only nominee who’s won before), and many were surprised she was nominated at all for a film that critics and audiences alike don’t seem to be responding to. Also, there’s a belief that “Jewell” is Eastwood’s closet defense of Trump (it’s about a man hounded by the media and the FBI), and are–obviously–not eager to reward that.

4. Florence Pugh, “Little Women”…If people are going to vote for a “Little Women” performance, it would more likely be Ronan’s, but this isn’t a bad result for Pugh–her first nomination, and a sign of things to come.

3. Scarlett Johansson, “Jojo Rabbit”…”Rabbit” may be a stronger movie than many voters realize. [It scored a surprise Best Picture nomination and has done so at some of the other Pre-Oscar awards indicators.] And if people feel Johansson deserves to win for one of her two nominations (weirdly enough, actors don’t typically win in the years they have performances nominated in lead and supporting categories), and Zellweger is a lock for Best Actress, they may vote for her here. But I suspect that’s an unlikely outcome.

2. Margot Robbie, “Bombshell”…Many people would be surprised to see Robbie as my pick to upset Dern, but she was great in two separate 2019 movies, is widely liked, and her “Bombshell” character is fictional, so people wouldn’t necessarily be rewarding a real-life Republican (unlike with Theron). The #MeToo movement may have just struck enough of a cord with female voters—who don’t really like “Marriage Story” anyway—to feel Robbie’s degradation at the hands of Roger Ailes closely mirrors their own experiences. Robbie winning for this performance may be the ultimate way to send a message.

Winner: Laura Dern, “Marriage Story”…Although my gut is telling me something will go wrong here (Dern is the softest frontrunner in the acting categories and Oscar likes to throw one curveball a year), the other nominees aren’t strong. [She definitely dodged a bullet by Jennifer Lopez not being nominated.] I still think this is the most competitive Oscar acting category, but (right now) it’s hard to see which young ingenue out of Pugh, Johansson, and Robbie has the best chance at beating her, which may lead to vote splitting. And Dern is widely liked (for good reason), and never won before.

Who Should Win: Margot Robbie, although I love Dern as an actress, her role in “Marriage Story” isn’t really meaty enough to win an Oscar. What is that character’s inner-life? Does she even exist outside of her work for Johansson? We don’t see it, if she does. But Robbie gets a light-hearted lesbian liaison with Kate McKinnon, harassed by John Lithgow’s disgusting media tycoon/tyrant, discusses her philosophy and politics (which might contradict with what she does in the moment), and is just an all-around better developed character and more layered performance.

Who Should’ve Been Nominated: Although I would’ve loved to have seen Julia Fox (“Uncut Gems”) or Taylor Russell nominated for her nuanced, sensitive, quietly spellbinding work in “Waves,” the real snub is–of course–Jennifer Lopez in “Hustlers.” Many expected her to be nominated, as actually was the Best Supporting Actress of the year in a performance that is ferocious, calculating, mesmerizing (you can’t take your eyes off her), and mildly villainous, unlike anything we’ve seen from her before. It would’ve been one of the rare times when the actual “Best” goes to the actual best performance.

Who Will Win Best Director…

5. Todd Phillips, “Joker”…Although Phillips actually fully deserves this nomination (he’s never made a drama before, and this is easily the biggest stretch directing-wise out of this category), he’ll be a divisive choice in a category that has indie darlings (“Parasite”), living legends (Scorsese, Tarantino), and a technically difficult war movie (“1917”).

4. Bong Joon Ho, “Parasite”…Even if this movie has a devoted cult of fans that are ready to throw awards at it, I still think the competition is a little bit too stiff for Ho to breakthrough here, especially since he’ll more likely win in the screenplay and foreign film categories…and especially since the most famous director alive not named Steven Spielberg (Quentin Tarantino) is nominated, has never won, and still isn’t the favorite.

3. Martin Scorsese, “The Irishman”…Really, this is the movie he should be winning for instead of “The Departed,” but enthusiasm for this seems to have cooled considerably. Even though a lot of the older voters will vote for Scorsese, even some of those are reluctant to award a Netflix film that received a practically-non-existent theatrical release.

2. Quentin Tarantino, “Once Upon a Time in Hollywood”…Believe it or not, Tarantino has never won Best Director before (only nominated for “Inglorious Basterds” and “Pulp Fiction”). He has said he’ll only make 10 movies, and this is the 9th–so Oscar voters may not get another chance. That being said, the frontrunner for this is clearly…

Winner: Sam Mendes, “1917”…The tricky one-shot cinematography (the movie is designed to look like it’s all one take) is clearly the stand out. People like to recognize directors of movies that look technically difficult to pull off (“Gravity,” “The Revenant”). The Director’s Guild awarded him (their winners almost always overlap with the Academy’s), but I still believe Tarantino has an outside chance here.

Who Should Win: When I posted this very thing a few things (“Who Will Nominated for Oscars and Who SHOULD Be”), Mendes was actually the only one of these I picked as someone who should be nominated. At the time, I had just seen–and been completely swept up by–“1917” and even though I still do think it’s a great movie, “Joker” and “Once Upon a Time in Hollywood” grabbed me more. Phillips had a command of “Joker” that nothing he had done before would lead you to believe he possessed, he was beyond capable–pulling you like gravity through a dark world he had total control over. “Once” was also a case of a director who was perfectly relaxed and at the height of his powers. Honestly, I’d be happy if any of these three won.

Who Should’ve Been Nominated: I would’ve loved to have seen Gurinder Chadha (“Blinded By the Light,” an underrated musical that gets you inside the power music has to move people in a way few musicals understand), Trey Edward Shults (“Waves,” pulling off an experience I’ve never had with a movie before), and especially James Gray (“Ad Astra,” combining an intimate family drama with vast space adventure to get a futuristic Greek tragedy) all nominated. But I think Robert Eggers (“The Lighthouse”) is a showing a great example of a director’s movie, creating a mood like no other. And I’m at least hoping it’ll win Best Cinematography.

Who Will Win Best Picture…

9. “Ford vs. Ferrari”…Even though I loved this movie (it was one of my top 20 of the year) and it’s actually become underrated by critics and awards shows alike, there’s no doing that the momentum seems to have stalled out–pun intended. It’s not nominated in any other major category, and Christian Bale was snubbed for Best Actor, signaling soft overall support.

8. “Jojo Rabbit”…Many (like myself) are very surprised that this movie is as popular as it is, and would’ve rather seen “Knives Out,” “The Farewell,” or (my pick) “Ad Astra” nominated instead. If voters want a war movie, “1917” certainly seems more likely and prestige dark comedies are also well-represented with “Marriage Story” and “Once Upon a Time in Hollywood.” Thanks “Jojo,” but we’re good…

7. “Little Women”…While some may vote for this just to make up for Greta Gerwig’s perceived snub for Best Director, if voters are really and truly being honest with themselves that wasn’t much of an actual snub. “Little Women” is much more old-fashioned than many of the actual top Oscar contenders. It’s very hard to watch it and then “Joker,” “Once,” “1917,” “Parasite,” “The Irishman” and even “Jojo Rabbit” and say “now this is daring filmmaking I haven’t seen before!”

6. “A Marriage Story”…A movie that many people don’t like that much, and unlike other movies that received blowback on social media (“Joker,” “Hollywood”), “Marriage” has a very soft base of support to make up for that. Like Gerwig, Noah Baumbach wasn’t nominated for Best Director and this seems like a very competitive year for a movie that wasn’t nominated in that category to slip into the top spot.

5. “Parasite”…The cult behind this movie is strong, but the competition is just too strong this year. Plus, “Parasite” is a favorite for Best Original Screenplay and Best Foreign Film. Many may think “that’s enough.”

The real race is the top 4, as theoretically any of these movies could win…

4. “The Irishman”…A lot of older Academy voters will be voting for this impressive, somber epic, but I feel general support is soft. [Despite a lot of nominations, it’s unlikely to win in a major category.] I do think this is a much better movie than “The Departed,” but since Scorsese won Best Director and Picture for that, voters may feel “enough” for the gangster epics. [And some older voters still aren’t comfortable with the idea of “Best Film” winner being released almost exclusively on Netflix.] It still wouldn’t surprise me at all if this wound up winning though.

3. “Joker”…There is a massive disconnect between Twitter hashtags and Oscar voters. Many in social media would probably be shocked that I’m ranking this movie’s odds higher than “Parasite” or “Little Women,” but I actually should be ranking it higher still. It has massive box office (first R-rated movie EVER to gross a billion dollars), a devoted following, and also received the most number of nominations this year–despite tech-heavy movies like “1917” and “The Irishman” probably should’ve gotten more due to their more complicated technical aspects. That signals a lot of support for this movie. And “Greenbook” was universally despised by the Twitterati and still won last year, perhaps as a blowback to the social media reactions. Really the only thing holding it back is that a lot of older voters may not go for it like they did “Greenbook,” and a quick look back at Oscar history shows they haven’t been favoring violent, edgier movies since the late-2000s (“The Departed,” “The Hurt Locker,” “No Country for Old Men”). Can the last movie of the 2010’s break that pattern?

2. “Once Upon a Time in Hollywood”…Just like Tarantino has never won Best Director, no film he’s made has won Best Picture either. This would seem to be the year. This is a widely liked movie, most of the most negative social media reactions have gone to “Joker” (seen as more divisive), it’s a massive box office hit, and–unlike “The Irishman”–it’s a triumphant example of mature, adult movies still having an audience that wants to watch them in a movie theater. The only thing giving me pause about this winning is that it did not win “Best Comedy” at the Golden Globes (beaten by “Rocketman” is a bit pitiful) or Best Cast at the Screen Actors Guild Awards. Those were awards where “1917” wasn’t even nominated, and it still didn’t win. That may indicate softer overall support, but (unlike “Joker”) I could actually see this playing relatively well with older voters–who are perhaps nostalgic for the period represented here.

Winner by a nose: “1917”…Although I feel an upset in my gut (remember when no one thought “Moonlight” could beat “La La Land”), there’s no denying this is the frontrunner with huge wins for Best Drama at the Golden Globes, Best Film at the BAFTAs, and Best Movie at the Producer’s Guild Awards. [Although people mistakenly think the PGA is the ultimate indicator of Best Picture, they picked “La La Land” and “The Big Short” recently when the Academy did not.] Although to me those wins are explained by the Golden Globes and BAFTAs favoring British movies more than the Academy does, and the PGA just going with whatever it thinks will win. The biggest thing helping “1917” (a movie that has only one female in its massive ensemble) is that the other three frontrunners are seen as even more sexist, and possibly more violent. It’s not everyday a war movie made up entirely of tracking shots is seen as the “safe” choice, but it just might be.

Who Should Win: Out of the nominees given, “Joker” and “Once Upon a Time” were my favorites–sue me Twitter. “Hollywood” is just an enjoyable, excellent experience all the way through, that manages to show the exact moment when Hollywood was changing, the country turned on the “hippies” (the Manson murders), the 60’s became the 70’s, and how all that could’ve been averted if the Manson murders never happened, stopping DiCaprio’s aging cowboy from becoming a Republican like Tom Selleck or Clint Eastwood. [The final shot of Cliff leaving in the ambulance, unable to follow DiCaprio’s vulnerable leading man into the New Hollywood is a perfect callback to “The Searchers”.] And “Joker” speaks perfectly to the moment we’re in in a way that something like “1917” just simply does not.

What Should’ve Been Nominated: None of my top 5 of the year were nominated–“Waves,” “American Factory” (although of course that has a great chance of winning Best Documentary), “Dark Waters,” “The Lighthouse,” and the underrated “Ad Astra,” the best film of 2019.

That’s all the categories I feel like going in-depth on, although I sure hope “The Lighthouse” wins Best Cinematography, and “American Factory” wins Best Documentary. Also, if “1917” loses Best Picture–and I heartily suspect it might–then I’ll be kicking myself come Sunday night for not trusting my instincts.

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