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The Best Bets When Gambling On The 2020 Oscars

It has finally arrived. The Super Bowl of Hollywood. The Academy Awards (the Oscars if you're not a snob) are finally here. But what is going to win? What movies and stars are the favorites? What nominees have the best shot at pulling the upset? What is worth betting on? I am going to try and answer it all...

MAJOR DISCLAIMER: None of these are locks! Predicting award shows can be difficult, betting on them is even harder. The goal with this guide is to help give you the best bets to make a nice penny off of the award show. Think “low risk, high reward” when it comes to the Oscars. The odds are crazy high in some categories, so a light sprinkle is usually all you need. As always, bet with caution, nothing is a sure thing.

Each category will be broken down in terms of value and what I find to be a nominee worthy of throwing some money at. To arrive at my determined values, I am using other awards show nominations and victories, thoughts from Barstool's own RearAd (a movie award show gambling man), thoughts from Walt Hickey, who runs a fantastic analytics model for awards season over at Numlock, and the Oscars matchup-voting model used (here) by James England.

REMINDER: Tune in to our Oscars Livestream Contest (PFT Commenter, Marty Mush, Feits, KenJac and myself) on Sunday to help decide the punishment for the contest's loser...

Let's cut right to the chase and dive into what you should be looking at for Oscars Sunday...

2019 FAVORITE: Roma (-310)
2019 ACTUAL WINNER: Green Book (+340)

This year's Best Picture race is absolutely thrilling.

What was at one point a three-horse race is down two with the favorite '1917' and 'Parasite', the movie with all of the momentum. '1917' has won the majority of the precursor awards (mostly the Producers Guild win it had) and is the clear favorite, but the odds are actually pretty nice at -200. Meanwhile, 'Parasite' is close behind with some big wins of its own. A reminder that an upset happened in this category last year and the odds were quite similar when 'Green Book' toppled 'Roma'.

This is the analytics breakdown from Walt Hickey in regards to the "resume" for each of the Best Picture nominees...

You can also see that 'Once Upon a Time in Hollywood' has some solid value heading into the Oscars, but I would focus all efforts and bets on the top two choices.

The process in which the Academy votes for Best Picture is complicated, so I'll go back to Walt Hickey, who put together a very good breakdown of how it works and why this race is so wide open...

When I talk to folks about how the Oscar voting shakes out, the question tends to be something like, “I know 1917 won a lot, but I really like Parasite and I think that a lot of the Academy probably also does, and I wonder if the weird voting thing that they do means that the movie I like has a shot?”

Ranked choice is a process where people rank the Oscar movies on their ballot. The votes are all counted up, and if one movie has more than 50 percent of votes, that movie wins. If a movie doesn’t have 50 percent of votes, all the ballots that voted for the movie with the lowest votes get moved to their second choice. Then the process repeats until some movie breaks 50 percent.

The objective is to find the film most amenable to the largest number of people. As a result, it’s nice but not all that critical to get a massive pile of #1 rankings. Realistically, a nine-nominee field is not getting settled on the first ballot. What competitive movies need is to simply be ranked better than their top rivals. Last year, the fact is that a majority of the Academy ranked Green Book above Roma. It’s that simple. (via Numlock)

My favorite description of the Best Picture category is when people say it is basically "Least Disliked Picture." If you're really interested in the process even further, this is another great run-through of how it all works…

For me, there's just a vibe with 'Parasite' and the way people in Hollywood talk about it has me thinking it fits the bill for how the Best Picture voting works. The line has moved heavily in the favor of the movie this past week as well. Rear Ad is also on the 'Parasite' train with me on Sunday…

There's no question about what the Best Picture of 2019 is. The only question is will PARASITE be properly rewarded Sunday night. Due to prior particular wins on the awards circuit, 1917 is the favorite but the odds are hardly insurmountable (see: CRASH 2006 Oscars). And while 1917 is incredible filmmaking, I don't know that it's an incredible film; I don't think it was an industry-rattling war film like APOCALYPSE NOW or SAVING PRIVATE RYAN. I'm on PARASITE +400 to win Best Picture. Hopefully, the Academy isn't as scared of subtitles as Joe Six Pack is. (Either way, just don't let it be JOKER.)

Meanwhile, Walt Hickey sees both sides of the coin having value but wants to make sure you factor in the directors…

In terms of value, this feels pretty fairly priced. Something like a two-thirds chance of a 1917 win seems fair to me given the risks of how the voting is handled, but this was a short season and 1917 mopped up at all the right times, given its recent momentum that may even be underpriced. If you're bearish on 1917, keep your powder dry; in that case the real wager for you is in director where the money is better, because if Parasite topples 1917, we'll know it because Bong's beating Mendes. If you're bullish on 1917, I think you can actually hedge this one pretty well by buying both Bong and 1917, because a split decision seems tough given how essential the direction is for each of these works and the odds are better in direction.

There are a few ways to play Best Picture, but I have been on 'Parasite' all awards season and won't be backing off heading into the weekend.

2019 FAVORITE: Glenn Close, 'The Wife' (-480)
2019 ACTUAL WINNER: Olivia Colman, 'The Favourite' (+440)

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This major category also had an upset last year when Olivia Colman shocked everyone and beat out Glenn Close for the win. I actually had this category as a major value play last year, but this year the category is almost a near-lock for the favorite. Reneé Zellweger has won basically every award for her role in 'Judy' and you should expect to see her on the stage Sunday night. With that said, Walt Hickey brings up a good point as to why Scarlett Johansson isn't the worst nominee to take a chance on…

On one hand, Zellweger's functionally swept. On the other, Best Actress is insane, and Marriage story has been seen by a lot more people than Judy. +1000 isn't great, but if you want to roll the dice on a longshot in acting categories your best bet is probably ScarJo, a dual nominee, and Best Actress, where she's not competing against a dominant costar. Again, Zellweger's the favorite, but there's so little viable angles in the acting categories so if you're feeling particularly risk-happy that's my best pick for you.

With two nominations, the Academy and the people who nominate the categories clearly love Johansson, so it isn't totally crazy to think she might pull an upset in one of her two categories. James England's Oscars rankings further reinforce the point that people just simply didn't see 'Judy' (they didn't see 'The Wife' with Glenn Close last year either… except for Barstool's own Rone, he loved the movie), meaning Johansson might be less of an underdog than we think. Rear Ad also sees some potential here…

Renée Zellweger (-2500) seemingly wrapped up Best Actress once JUDY dropped. While people rave about the role, nobody raved about the movie so I wonder if that might open the door for Charlize Theron (+2500) or Scarlett Johansson (+1000).

Tough! This category isn't a priority of mine, but the reasonings to not totally ignore it are fairly justifiable. If we are going to see a shocking upset on Sunday night, this might be the spot.

2019 FAVORITE: Rami Malek, 'Bohemian Rhapsody' (-500)
2019 ACTUAL WINNER: Rami Malek, 'Bohemian Rhapsody' (-500)

ME: Do not waste your time.

WALT:

I don't see much of a play here, Driver is great but has been throwing up blanks all season and +1000 isn't enough to get me interested.

REAR AD:

The acting categories all feel like foregone conclusions and that stinks because it takes away so much suspense from the show. When fucking Leo is +5000 for Best Actor, then you know Joaquin is pretty much a slam dunk (also, the -5000 for Phoenix is kind of a giveaway). If there is going to be a spoiler here, it'll be from an also-deserving Adam Driver (+1500).

This isn't even a contest anymore. I guess in a crazy world Adam Driver still has a chance, but Joaquin Phoenix is as big of a sure-thing as it gets when it comes to the Oscars.

2019 FAVORITE: Regina King, 'If Beale Street Could Talk' (-280)
2019 ACTUAL WINNER: Regina King, 'If Beale Street Could Talk' (-280)

Laura Dern has won every award leading up to the Oscars so we have a pretty clear foregone conclusion on our hands. The acting categories are sort of boring this year, especially in this category and everyone knows it. From Rear Ad…

Laura Dern (-2500) also feels like a foregone conclusion and while I'm a big fan of her work, her performance didn't scream "Oscar" while I watched it. BOMBSHELL sort of came-and-went so I don't know if Margot Robbie (+1400) has much momentum. I don't have any action here but at +6600, I'd throw a couple of shits and giggles shekels on Kathy Bates just because I'm a sucker for huge odds.

…to Walt Hickey (who summed up both supporting categories)…

Both of [the Supporting categories] are basically cooked, Dern and Pitt have done all the politics perfectly for years of buildup and have had flawless seasons. Not saying these are as good as savings accounts, but they're not worth it.

I will note that the same logic I used for Best Actress does also apply here because I can't totally rule out Scarlett Johansson and her two nominations. James England's model actually has Florence Pugh at the top of the list, but I can't see anyone other than Johansson pulling what would be an absolutely stunning upset.

2019 FAVORITE: Mahershala Ali, 'Green Book' (-370)
2019 ACTUAL WINNER: Mahershala Ali, 'Green Book' (-370)

Rinse, lather, repeat with the male side of the Supporting acting category. Brad Pitt has been unbeatable and even fired up some legendary speeches…

Rear Ad is a little more optimistic about this category going a different way…

Brad Pitt is the chalk (-4000) going against titans like Pesci, Pacino, Hanks, and Hopkins. And Pitt was fantastic in the role. But I wouldn't be surprised if Pesci steals it with his brilliant, understated performance so he's worth a small taste at +1700.

I just don't see it. This whole campaign has felt a lot like that of J.K. Simmons for 'Whiplash' a few years back. Best Supporting Actor is traditionally the first award of the night and I expected Pitt to be the first to make a speech. If anything crazy goes down, this could be the spot for 'The Irishman' to make its mark. I'll favor Al Pacino here just due to the size of the odds, but if you're going to take a big risk, Joe Pesci would be worth it as well.

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2019 FAVORITE: Alfonso Cuaron, 'Roma' (-1350)
2019 ACTUAL WINNER: Alfonso Cuaron, 'Roma' (-1350)

Okay folks, now we have a little something to play with here!

The line has moved a ton for 'Parasite' director Bong Joon Ho over the last few days, even though all previous award shows this year make Sam Mendes a near-lock for the award. The last time a winner of Best Director did not also win the top prize at the Directors Guild of America Award was in 2012 when the Oscars didn't even nominate Ben Affleck for 'Argo'. History is very much on the side Mendes, and I would expect him to win, but I am absolutely taking a chance on Bong Joon Ho. Rear Ad is doing the same…

Sam Mendes is the chalk (-600) for Director and is certainly deserving for his work. But I'm the conductor on the PARASITE train so I'm on the Bong (+400).

Walt Hickey also has a good theory and method if you think Bong Joon Ho can challenge Mendes…

If you want to make a gamble in Best Picture, this is where you should actually be doing it. If you want to bet on Parasite, you should bet on Bong here instead, the +325 is better than the +275 you'd get in Best Picture. If you think that the only possible contenders for the Oscar are Parasite and 1917, and if you think that the longstanding trend of best picture is linked to best director, there is a play here; Consider what would happen if you bet $150 on 1917 and $70 on Bong.

The hype train for 'Parasite' is really hard to ignore in all categories. Just look at the standing ovation the cast got at the Screen Actor Guild Awards before they won the top prize…

Just like it did with Best Picture, James England's model also favors 'Parasite' in this category. I would strike now before the odds continue to even up…

2019 FAVORITE: 'Spider-Man: Into the Spider-Verse', (-1200)
2019 ACTUAL WINNER: 'Spider-Man: Into the Spider-Verse', (-1200)

I can't remember the last time the Best Animated Feature race was this wide-open, especially with a major Pixar property like 'Toy Story 4' in the mix. There aren't many nominees on the board from Netflix that look like they have a strong shot, so 'Klaus' from the streaming company could be worth a play in this category.

While I have a hard time seeing Pixar losing this category with Woody and Buzz as their representatives, it is worth noting that 'Missing Link' won at the Golden Globes. While that whacky show doesn't really predict the Oscars, having it sit here with +800 odds is tough to pass up. Walt Hickey agrees…

That's an outstanding price for Missing Link, winner of the Golden Globe. Nobody is good at foreseeing animation prizes, no precursor is predictive, and the studio LAIKA has been throwing themselves at this wall for years. I'll take that price.

This is the most wide-open category of the night and without much to base your selection on, it's a total crapshoot. But don't turn away from a solid amount of value plays from the animated field.

2019 FAVORITE: 'Free Solo'
2019 ACTUAL WINNER: 'Free Solo'

I am personally very surprised that 'American Factory' isn't an even stronger favorite due to the Netflix angle and the fact that it is the first movie produced by Higher Ground Productions, former President Barack Obama and Michelle Obama's production company. Because of the line being at -265, I think it's worth giving a strong look at 'Honeyland', a movie causing a lot of buzz in Hollywood (Matt Bomer, in an interview with Lights Camera Barstool, even mentioned it as one of his favorite movies of 2019).

Walt Hickey agrees with me on the "bee movie"…

Literally nobody knows what's going to happen in Doc, not even oddsmakers, not even documentarians. Anything's possible here, I'd take those Honeyland odds.

If you don't want to get too crazy but still some juicy odds, 'For Samais probably worth a look in this category.

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2019 FAVORITE: 'The Favourite' (-210)
2019 ACTUAL WINNER: 'Green Book' (+190)

It's hard for me to go against 'Parasite' in any category where it is deemed the "favorite," especially with favorable odds at -265 right now. Following its win at the Writers Guild of America Awards, Bong Joon Ho probably has a win here. You could make a case for 'Once Upon a Time in Hollywood' and Quentin Tarantino here considering this might be a bit of a consolation prize for the love-letter to Hollywood assuming it doesn't win Best Picture.

Walt Hickey doesn't see much value here…

These categories are much harder to predict and could go either way, I don't see a lot of plays in either, and the prices are set really well so I don't see an angle.

'Green Book' pulled the upset last year and it is a fairly unpredictable category. I think if you're dying to put your name on every category, there are two clear plays here, but this isn't the sexiest option of the night.

2019 FAVORITE: 'BlacKkKlansman' (-370)
2019 ACTUAL WINNER: 'BlacKkKlansman' (-370)

The favorite in this category did win in 2019 as Spike Lee won for 'BlacKkKlansman' and I think this year's front-runner 'Jojo Rabbit' is a pretty strong bet. I mean, who wouldn't want to see 'Thor: Ragnarok' director Taika Waititi on stage?

With that said, I still see value in possibly sprinkling something on Greta Gerwig and 'Little Women' and 'The Irishman'. The reason? I don't trust Oscars voters. I've seen tweets and comments about voters not loving 'Jojo Rabbit' and the very lovely "film twitter" has been up in arms about the movie at times. Now, this likely won't have a heavy impact on the writing side of things here, but it is enough to give me some pause.

Walt Hickey disagrees and sees little-to-no value…

I don't like any of these prices, except maybe the Irishman as a longshot?

Use caution, but there is a small upset vibe with this category.

--
How about some of the other categories…

SOUND MIXING & EDITING: I think sprinkling 'Ford v Ferrari'  (+150 in Editing, +175 in Mixing) in these categories is worth it, '1917' is the favorite in each individual category and I could see the movies splitting this award. It's worth noting that there have been plenty of times where the same movie will take both awards.

BEST VISUAL EFFECTS: While the technical aspect of '1917' is its strongest sellest point outside of Cinematography (a lock in that category, by the way… shoutout Roger Deakins), the same can be said for the de-aging effects from 'The Irishman'. There's a chance Scorsese's Netflix epic could get shutout of the Oscars if it doesn't grab a win in this category. At +550, it might be worth a thought in regards to entering this category.

BEST PRODUCTION DESIGN: I don’t think any movie is a lock in this category so the lines of 'Once Upon a Time in Hollywood' (-167), '1917' (+200) and 'Parasite' (+375) all look pretty damn attractive. If 'Parasite' has a night where it cleans up, it makes sense that this would be one of the categories, and the same can be said about '1917'.

BEST FILM EDITING: The lines in the Film Editing category are also pretty intriguing with 'Parasite' (-110) and 'Ford v Ferrari' (-106). Overall, the technical categories have the best competitions at the Oscars this year.

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Let's recap my favorite plays of the night…

Huge thank you to Rear Ad and Walt Hickey for their input (read Walt's Oscars breakdowns, they're excellent) into gambling on this year's show.

As always play at your own risk and see you on Sunday night for the Oscars.