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The Gauntlet’s Academy Awards picks

By Troy Hasselman and Matthew Herring, February 7 2020 —

The Academy Awards are upon us with the show taking place this coming Sunday night. In anticipation of this, myself and my trusted Arts Assistant — Matthew Herring — are unveiling our Oscar’s picks. We’re taking a look through all of the major categories and making a guess as to who will win each award and who should win each award. We analyzed, we checked the betting odds, but mostly we got mad about Adam Sandler getting snubbed for his performance in Uncut Gems. 

Best Picture



Jojo Rabbit

The Irishman

Ford V Ferrari

Little Women


Marriage Story

Once Upon a Time… In Hollywood

Who will win 

Matthew’s Pick: The Irishman

I’ll admit it. I haven’t seen The Irishman, nor do I have any intent in enduring 210 minutes of mafia-related drama and inconsistent de-aging technology. However, as one of the most acclaimed directors of all time — and even though the odds aren’t looking great for it winning — Martin Scorsese has never won a Best Picture Oscar, and they’ve got to give it to him eventually, right? Though I won’t be happy if this wins, at least it’s not Joker

Troy’s Pick: 1917 

In what will be an anticlimactic end to an awards season in one of the most impressive years for movies in recent memory, Sam Mendes’ style-over-substance war-drama 1917 is more than likely going to walk away with the Best Picture award. While the one-shot concept of the film is interesting and Roger Deakins’ cinematography is as brilliant as always, the movie ultimately doesn’t have anything to say that hasn’t been already said by countless other Academy Award Winners. Based off the predictable nature of what kind of movie wins Oscars, and it’s previous wins at the Golden Globes, BAFTA’s and SAG Awards 1917 is as sure of a lock as it can get for a winner. 

Who should win

Matthew’s Pick: Parasite

Parasite is crazy. After having the pleasure of watching it on three separate occasions, I’m pretty confident in saying that Parasite is the best movie ever made. Every moment is exhilarating as you wonder what twist could possibly be thrown at you next. No movie has ever had me rocking back and forth on the edge of my seat with anxiety like Parasite — though Uncut Gems is close, which by the way, is not nominated for any Oscars that year. Huh!

Troy’s Pick: Parasite

There’s no other movie in 2019 that captured what living in that year felt like more than Parasite did. Bong Joon-Ho’s class allegory is a harsh depiction of our times, but also a perfectly made movie. The plot is an ingenious tension-filled roller coaster ride that changes in tone on a dime and is sheer entertainment throughout while being near pitch-perfectly acted, shot, written, set and directed. While I wouldn’t place any bets on it to win, Parasite is the movie most deserving of the Best Picture title.

Best Actor in a leading Role

Antonio Banderas – Pain and Glory

Leonardo DiCaprio – Once Upon a Time… In Hollywood

Adam Driver – Marriage Story

Joaquin Phoenix – Joker

Jonathan Pryce – The Two Popes

Who will win

Matthew’s pick: Joaquin Phoenix – Joker

We all know that Joker is going to win at least one of the big awards, whether we like it or not. It doesn’t deserve any of these awards, but I guess if you’re going to give it anything, give Joaquin Phoenix Best Actor.

Troy’s pick: Joaquin Phoenix – Joker

While Joker itself spun it’s plot out in so many different directions that its message became meaningless and it has also spanned one of the most insufferable conversations surrounding a movie that I’ve ever seen, Joaquin Phoenix has been nearly universally hailed for his performance and has taken home awards already from the Golden Globes, BAFTAs and SAG Awards. No reason to think he won’t add an Oscar to that list.

Who should win

Matthew’s Pick: Leonardo DiCaprio – Once Upon a Time… In Hollywood

While Leonardo DiCaprio’s performance in Once Upon a Time… In Hollywood is great, his performance is overshadowed by the roles of Choi Woo-shik and Adam Sandler in Parasite and Uncut Gems respectively. This outcome is fine, but come on, did you see Adam Sandler?

Troy’s Pick: Joaquin Phoenix – Joker

 I didn’t like Joker, but Joaquin Phoenix is brilliant in Joker because he is brilliant in everything. I’m not really blown away by anyone that was nominated in this category this year, so I’d be happy to see Phoenix win it out of any of the nominees and I can just pretend that he’s winning it for The Master. His acceptance speeches have all been interesting at the other award shows and the Oscars will give him his biggest platform yet to say something eccentric and cutting. Though this category is ultimately meaningless considering that the best performance of 2019 — Adam Sandler in Uncut Gems — wasn’t even nominated.

Best Actor in a Supporting Role

Tom Hanks – A Beautiful Day in the Neighborhood

Anthony Hopkins – The Two Popes

Al Pacino – The Irishman

Joe Pesci – The Irishman

Brad Pitt – Once Upon a Time… In Hollywood

Who will win

Matthew’s pick: Brad Pitt – Once Upon a Time… in Hollywood

It feels wrong to categorize Brad Pitt’s role in Once Upon a Time… In Hollywood as a supporting actor. His role in the movie is equally as important as Leonardo DiCaprio’s, but hey, he qualifies for the supporting actor role. Get that bread, Brad.

Troy’s pick: Brad Pitt – Once Upon a Time … In Hollywood

While Brad Pitt has won an Oscar for producing past Best Picture winner 12 Years a Slave, he’s never won an acting Oscar which is shocking to me. He’s Brad Pitt! You would have figured he’d have one by now. But it looks like this weekend is his time considering all of the other awards he’s won this season.

Who Should Win

Matthew’s Pick: Brad Pitt – Once Upon a Time… In Hollywood

See above.

Troy’s Pick: Brad Pitt – Once Upon a Time… In Hollywood

Brad Pitt is great in Once Upon A Time… in Hollywood and he fully deserves for this to be the movie he finally gets his acting Oscar for. His speeches have been funny at all of the award shows and every Oscar is basically a lifetime achievement award anyways. Why not? 

Best Actress in a Leading Role

Cynthia Erivo – Harriet

Scarlett Johansson – Marriage Story

Saoirse Ronan – Little Women

Charlize Theron – Bombshell

Renée Zellweger – Judy

Who will win

Matthew’s pick: Renée Zellweger – Judy

According to my Letterboxd account, The Bee Movie is the only Renée Zellweger film I’ve ever seen. I’m sure her role in Judy is great, hence the Best Actress nomination, but in my mind she will forever be engrained as the human woman who dated bee Jerry Seinfeld. Anyway, I checked the odds and it looks like she is going to win this category.

Troy’s pick: Renée Zellwegger – Judy

I actually saw Judy when it was making the festival rounds in the autumn and my thoughts on the movie were “Renée Zellwegger is probably going to win an Oscar for this,” and I haven’t thought of the movie since. I scarcely remember a detail from Judy but if all the other award ceremonies and the betting markets are an indication, I was probably right in my assessment. 

Who should win

Matthew’s pick: Saoirse Ronan – Little Women

It’s tough to articulate why Saoirse Ronan is so good in Little Women without simply pointing to the movie and demanding that you watch it. Maybe it’s the chemistry between director Greta Gerwig and Ronan, or maybe it’s the moment where she pleads with Timothée Chalamet that she does not love him. No matter what it is, it’s great.

Troy’s Pick: Saoirse Ronan – Little Women

Little Women is a ridiculously charming movie and Saoirse Ronan is ridiculously charming in it. Like Joaquin Phoenix, she is great in everything she does and she has the accolades to prove it, considering this is her fourth nomination at 25 years old. She will eventually win an Oscar, but as for all great actors it will come a few decades into her career unless she fast tracks herself by playing the Joker or starring in a war movie in the next year.

Best Actress in a Supporting Role

Kathy Bates – Richard Jewell

Laura Dern – Marriage Story

Scarlett Johansson – Jojo Rabbit

Florence Pugh – Little Women

Margot Robbie – Bombshell

Who will win

Matthew’s pick: Laura Dern – Marriage Story

Laura Dern is fine in Marriage Story. She plays a pivotal role in the movie, but doesn’t stick out in my memory like some of the other nominees for Supporting Actress. I’d be fine if she won, as she adds a lot to the intense emotional drama of Marriage Story, but she’s definitely not my first pick. Anyways, I was thinking, and you could probably swap the Randy Newman-composed soundtracks of Marriage Story and Toy Story 4 and you wouldn’t be able to notice a difference. 

Troy’s Pick: Laura Dern – Marriage Story

Laura Dern is the best and she’s the odds-on favourite to win the Best Supporting Actress Oscar. Though I liked Marriage Story well enough, hers will be yet another case of an amazing actor that doesn’t receive recognition from the Academy until they are decades into their career. Though I would prefer if she won for Blue Velvet or Wild At Heart or this show-stealing cameo on her daughter’s Tik-Tok account, I’ll be happy to see her recognized.

Who should win

Matthew’s pick: Florence Pugh – Little Women

With her starring role in Midsommar, it’s absurd that this is the only category that Florence Pugh is nominated in. Thankfully, Pugh is just as brilliant in Little Women. Playing the misunderstanding but loving sister Amy, Pugh perfectly encapsulates the family drama of the movie.

Troy’s pick: Florence Pugh – Little Women

Florence Pugh is the MVP of 2019. She brought a sympathetic turn to the historically maligned role of Amy March in Little Women, not to mention her terrifying and devastating star-turn in Ari Aster’s horror-opus Midsommar. She just turned 24 last month and is ergo too young for an Oscar but I know who really deserves the statue on Sunday night.

Best Original Screenplay

Rian Johnson – Knives Out

Noah Baumbach – Marriage Story

Sam Mendes & Kristy Wilson – Cairns – 1917

Quentin Tarantino – Once Upon a Time… In Hollywood

Bong Joon-Ho & Han Jin Won – Parasite

Who will win

Matthew’s pick: Bong Joon-Ho & Han Jin Won – Parasite

Maybe I’m being optimistic, but with the cultural impact Parasite has had with American audiences, it has to win at least one award. It’s deeply satisfying watching Ki-Woo and his family con their way into riches, and with all its twists and turns throughout its runtime, Parasite is the clear contender for original screenplay.

Troy’s pick: Quentin Tarantino – Once Upon a Time… In Hollywood

The Academy loves Quentin Tarantino’s writing, which isn’t news considering this is his fourth nomination for this award and will be his third win if my prediction is correct. Once Upon a Time in Hollywood does all of the old Tarantino tricks exceptionally well. Flashbacks and non-linear timelines? Check. Endless historical and cultural references? Check. Twist ending? Check. Feet? Check. For that, I believe he will be rewarded.

Who should win

Matthew’s pick: Bong Joon-Ho & Han Jin WonParasite

See above.

Troy’s pick: Bong Joon-Ho & Han Jin Won – Parasite

Parasite is a genius-level plot that keeps you guessing as to what is happening next for its entire runtime, but aside from being a ride there are ample amounts of subtext, along with humor and heart without becoming overly sentimental. While it would be amazing to see Bong Joon-Ho and Han Jin Won win, I think that it’s just too much of an ask from the Academy. Like asking them to nominate Adam Sandler for Uncut Gems.

Best Adapted Screenplay

Taika Waititi – Jojo Rabbit

Greta Gerwig – Little Women

Steve Zaillian – The Irishman

Anthony McCarten – The Two Popes

Todd Phillips & Scott Silver – Joker

Who will win

Matthew’s pick: Taika Waititi – Jojo Rabbit

Jojo Rabbit doesn’t scream ‘Oscar winner’ to me, but hey, that’s what the betting websites say. I don’t have any strong thoughts about this one. It’ll be cool if it wins, but the position really deserves to go to Little Women. What a movie.

Troy’s pick: Steven Zaillian – The Irishman

The Irishman got 10 nominations and has to win at least one of the major categories, the screenplay of the Irishman is as good of a part of the movie as any to be recognized, and there is a lot of good in that movie. The acting awards seem to be more or less knotted up, so I’m going to put a win for The Irishman here.

Who should win

Matthew’s pick: Greta Gerwig – Little Women

It’s a shame that Little Women isn’t getting more recognition this year. If there were a “Movie That Made Matthew Shed the Most Tears” category, this would definitely be the number one nominee. Shamefully — and I hang my head low when I say this — I have never read Little Women. What I do know is that Greta Gerwig made a damn good movie.

Troy’s pick: Greta Gerwig – Little Women

Greta Gerwig managed to parse Louisa May Alcott’s over 700-page source material into a tidy two hour film while losing none of the emotional punch and charm that has made the novel such a touchstone over 150 years after its original publication. The shifting timelines of the film tie its plotline together as it follows the March sisters through their childhood and into adulthood and back again and made Little Women into something that was completely undeniable.

Best Director

Martin Scorcese – The Irishman

Bong Joon–Ho – Parasite

Quentin Tarantino – Once Upon a Time… In Hollywood

Todd Phillips – Joker

Sam Mendes – 1917

Who will win

Matthew’s pick: Sam Mendes – 1917

The Oscars love war movies, what can I say? Combine that love and admiration for war with a film that is brilliantly edited to look like one continuous shot, and the result is a clear winner for Best Director.

Troy’s pick: Sam Mendes – 1917

Though making the movie one-shot is certainly a good idea, I still believe what is well executed in this movie lies with its cinematography. Nevertheless, it’s swept every other award and when a movie does well most credit ends up going to the director, so congratulations Sam Mendes. I still don’t think you deserve it.

Who should win

Matthew’s pick: Bong Joon-ho – Parasite

Bong Joon-ho’s biggest accomplishment with Parasite is how effortlessly he is able to portray the grim realities of living in poverty and the extremes individuals are willing to go to better the losing hand that was given to them. Joon-ho uses every trick up his sleeve to communicate the absurd and frankly disgusting juxtaposition between the upper-class and lower-class people. Rarely does a foreign movie have the level of success in North America as Parasite has had, and I think that speaks to the brilliant directing that was able to make it an international success.

Troy’s pick: Bong Joon-Ho – Parasite

Matthew pretty much hits the nail right on the head for why I also think he should win Best Director so I will take this opportunity to say one last time that Adam Sandler was robbed for his performance in Uncut Gems.

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