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My Favorite Oscars Picks On DraftKings

Happy Oscars Sunday to all of those who celebrate!

Over on Draft Kings (available in NJ, IN, MI, LA, CO, MA, & KS), you can bet on tonight's Academy Awards, and, as always, there are some plays worth looking at. When it comes to the Oscars, history is a pretty good indicator, so I will reference the algorithm and method used by my friend Walt Hickey over on as I do every year (all of the bar graphs I post come from that website // thank you as always to Walt for letting me reference them). His model factors in other awards shows and how they've impacted the Oscars race in past years. It isn't a fool proof method, but can give us good insight into the categories, and who might take home Oscar gold. We should also go over the fact that a lot of these are longshots, or hefty underdogs, so make sure to look everything over carefully, and bet responsibly.


This category, the biggest of the night, has become a bit of a runaway this year. OPPENHEIMER is the clear favorite by a country mile, and it losing tonight would be one of the biggest upsets in the history of the Oscars.

With that said, if you're compelled to sprinkle one of the longshots, there are probably three worth looking at here:
- KILLERS OF THE FLOWER MOON (+4000): Second in line based on historical data and indicators, and it's a movie from Martin Scorsese, so it has a legend involved
- BARBIE (+3500): Third in line behind Oppenheimer, and it obviously was the biggest thing in movies for 2023
- THE HOLDOVERS (+3500): At one point seemed like a legit contender, and this feels like a CODA or GREEN BOOK type movie that could surprise and win… but, again, this is a historical favorite out front with OPPENHEIMER

POOR THINGS is also something worth looking at, but if you're going to risk anything here, I just don't see this movie breaking through for an upset. The way the Academy votes for Best Picture is different from all categories…

…and I just can't see this movie (which is fantastic, but a little strange and potentially off-putting for some) as a mainstream pick for the Academy to lift above the widely loved OPPENHEIMER.


Okay, now onto the plays I love…


I LOVE OPPENHEIMER (+240) in this category. Right now AMERICAN FICTION is the very deserving favorite, but we don't have a lot of historical indicators to go off of this year because of one huge reason: the Writer's Guild Association Awards hasn't happened yet. Due to the writer's strike, that award show, which would basically help us dunk home the true favorite, won't happen until April. If OPPENHEIMER has the historic night it is expected to have, I really think an Adapted Screenplay win for Christopher Nolan is in the cards.


This is the best race of the night, hands down. Throughout the Awards season the two have gone back and forth, but a recent win at the SAG Awards pushed LILLY GLADSTONE above EMMA STONE as the favorite. However, I say NOT SO FAST MY FRIEND…

Historical data would indicate that EMMA STONE (+150) is the play here. Based on the Walt Hickey model, Emma Stone is the favorite based on indicators, and I think there's great value in Stone grabbing her second Oscar victory.

This is truly a toss-up though, as last year Cate Blanchett won the BAFTA, and Michelle Yeoh won the SAG Award, with the latter winning at the Oscars. They rewarded the first-time winner over someone who has already won the award, and would they do that in back-to-back years? It's a fascinating category, and easily the most intriguing of the night.


I really don't care for MAESTRO, and it seems a lot like one of those movies that gets a lot of award season buzz, has split reactions from audiences and critics, and then wins zero Oscars. It actually feels a lot like 'American Hustle' from 2013, another Bradley Cooper vehicle. Now, MAESTRO, is far more disliked, and I think it's going to strikeout at the Oscars. This is the category Netflix is apparently pushing for hard, hoping MAESTRO wins, but POOR THINGS (+125) is going to get a lot of love tonight, and the grand style of the movie might get a payoff with this award. Plus money odds for a movie people like far more than the favorite? Count me in.

This seems like an obvious win for BARBIE, and it is the favorite, but if you've seen POOR THINGS (+100), you know the costumes in this movie fly off the screen. This area of awards could be a big run for POOR THINGS, and if it wins Makeup & Hairstyling, I could see it running right into a Costume Design win as well. Just as I said above, this movie as a plus money pick is a no-brainer to sprinkle something on.


BARBIE is likely going to win in this category, anything other than this movie grabbing the win would be a shock. The clear favorite is "What Was I Made For?", which has picked up a few wins this award season, and Billie Eilish and Finneas are looking for their second Oscar victory with the song. However, "I'M JUST KEN" (+450) won already this award season as well, and Ryan Gosling is apparently going to be performing the song with a ton of backup dancers tonight. This is more of a hunch play, but it will be a big social media moment, and this category has had some weird winners and upsets in the past. I just love the +450 odds here.


First off, SPIDER-MAN: ACROSS THE SPIDER-VERSE should've been nominated for Best Picture, and I think it should win this category. But with the legendary Hayao Miyazaki up for the award with THE BOY AND THE HERON (+135), it's an underdog worth looking at. If you're looking for some plus money plays tonight worth taking action on, this one should give you some interest.


Going against OPPENHEIMER as the favorite isn't exactly a suggested tactic for tonight's Oscars, but this category might be an example where it could fall victim to an upset. THE ZONE OF INTEREST (+150) is a movie (a great movie, but brutal story and watch) where the sound is essentially a key component to the storytelling, so it grabbing the upset victory would make a ton of sense, especially after it won the BAFTA for the category. This would be an upset, but not exactly as shocking one.


This is the only play I am throwing out here that isn't plus money, but that's because I do think GODZILLA MINUS ONE (-165) is still a great option. Sometimes you can just tell when there is momentum leading into the Oscars, and the sentiment around this movie is too strong to look away from on the night of the awards. A few weeks ago, this was plus money, and I told people to get in on the action now. It very well might payoff if you got in early!


Now for three plays I think you can think about, if you want to get in on some true dogs…


This is that area of the night where we could see a run for POOR THINGS, but I wouldn't rule out OPPENHEIMER (+1400) for Production Design. The sets built for that movie were massive, whether it be the whole Los Alamos town, the site of the Trinity Test, or the Oval Office. Few movies have won 10 Oscars (Oppenheimer is going to get screwed by them combining the Sound Mixing & Editing awards), and if OPPENHEIMER does it, it will likely be because of an upset in this category.


Over the last few weeks this category has gotten less and less interesting, as Cillian Murphy has grabbed wins at the BAFTA and SAG Awards. 

He's the pretty heavy favorite, especially factoring in the historical data, but there is just something about PAUL GIAMATTI (+600) that might be worth a small play. Giamatti is beloved in the industry, has truly never gotten the proper recognition on the biggest stage, and has had a great award season campaign. This has evolved into what would end up being a huge upset, but I can't pretend I would be blown away if Giamatti snuck in for a surprise win.


There is one reason, person actually, to think about taking KILLERS OF THE FLOWER MOON (+1400) in this category: Thelma Schoonmaker. Martin Scorsese's longtime, iconic editor has won three Oscars in the past, and now has her ninth nomination. This is another category where OPPENHEIMER is the clear favorite, but if you told me there was going to be a wild upset at the Oscars, I would guess this category has potential to be such.

Good luck on any plays you take tonight, and, as always, please bet responsibly.