How to win (and probably lose) some money betting on the 2020 Oscars

It has come to our attention that there is a new way to gamble your money away. Last year, the New Jersey Division of Gaming Enforcement gave sportsbooks the all-clear to accept wagers in NJ on the Oscars and now Indiana has joined the party. Since its inception, The Loop has strived to be the one-stop-shop for betting of all shapes and sizes, thus we wouldn’t be doing our due diligence if we were to scrimp out on film's biggest night now. So buckle up (and pony up) as we break down of the best bets of the 92nd Academy Awards. Let's make some money back on those Super Bowl losses, shall we?

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BEST PICTURE

What once seemed like anyone's game, this race has narrowed drastically over the past month or so. With a late release in NY and LA on Christmas, 1917 has shot up to the top of the list in a way that didn't seem feasible. Before it opened wide, the war epic took home the two biggest prizes at the Golden Globes (Drama and Director) and since then has done a near clean sweep of all of the Guild Awards, which are oftentimes the best forecaster of who succeeds Oscar night. The Sam Mendes one-shot war thriller is clear Oscarbait—male-dominated, showy filmmaking and a World War epic—and with the shortened awards schedule, there doesn't seem to be enough time for another narrative to grab hold. Also, if Mendes can win for American Beauty, he can win for anything. The flies in the ointment are certainly Parasite and Joker. Parasite has the enthusiasm and support of the Screen Actors Guild, the largest contributing body, and Joker has the thinly-veiled social issue narrative that does well among voters. As much as I'd personally enjoy a Bong Joon-ho Parasite victory, Joker's 11 nominations mean that it has full Academy support and it's just chaotic enough that I can see it taking home the big prize if everything falls into place.

Winner: 1917 (-250)

If You Want to Make It Interesting: Joker (+1200)

BEST DIRECTOR

This is a two-horse race and it's pretty crazy that neither of those horses is named Martin Scorsese or Quentin Tarantino. Similar to Best Picture, the 1917 nominee has taken a clear-cut lead heading into the final few weeks. Since 1950, the winner of the Directors Guild of America award for Directing for Feature Film has gone on to win 90% of the time. There have only been seven years where those two have split. This year, Mendes took home the big DGA prize and has created a film that is catnip (shoutout to the abomination that is Cats) for the Oscars. A recent analog to the filmmaking of 1917 is Alejandro Iñárritu's Birdman, which also attempted a one-shot take to the entire movie. That went on to dominate the 2015 Oscars taking home the big two prizes in the same way that I see 1917 sprinting to a big finish. The only legitimate upset pick would be Bong Joon-Ho for Parasite, who has garnered a surplus of support, has become a meme and is doing enough press for two lifetimes. Bong also hasn't won an Oscar before, unlike Mendes. That could be enough to sneak him onto the stage. Now, watch Todd Phillips for Joker win, since I haven't mentioned him.

Winner: Sam Mendes, 1917 (-1250)

If You Want to Make It Interesting: Bong Joon-Ho, Parasite (+500)

BEST ACTOR

This competition ended the second Joaquin Phoenix donned the Joker makeup. Although the lead male actor category is stacked this season—Robert DeNiro, Adam Sandler, Eddie Murphy, and Taron Egerton all missed the cut—seemingly every award has made its way to Phoenix despite the opposition. The Best Actor trophy is usually given not necessarily for the best acting, but the most acting. And no one acted more than Phoenix. Look at the last decade and this section leans heavily into transformations. Since 2010, Rami Malek, Gary Oldman, Matthew McConaughey, Colin Firth, Daniel Day-Lewis and Eddie Redmayne all went the biopic "become a brand-new person" route and were rewarded heavily for it. Phoenix isn't playing a real person, but it's a similar role. The only alternative is Adam Driver, who somehow finds himself on the outside-looking-in. He took home quite a few smaller critics awards, which puts him in a clear second place. I don't see it happening, but if there's a stronger backlash against Joker than the nominations represented, Driver may have a sliver of a chance.

Winner: Joaquin Phoenix, Joker (-5000)

If You Want to Make It Interesting: Adam Driver, Marriage Story (+1000)

BEST ACTRESS

Out of all of the acting categories, this is the one that has the best possibility for an upset. Renée Zellweger has been hogging the Lead Actress prizes from the get-go including the Golden Globe Award, Screen Actors Guild Award, and Critics' Choice Movie Award, but I can see this going a bit haywire at the final moment. Last year, Glenn Close's performance in The Wife was a shoo-in to emerge victoriously and then at the eleventh hour, Olivia Colman swooped in and ended up on the stage for her performance in The Favourite. This season has a similar vibe to me, however, choosing between Zellwegger's fellow nominees is quite difficult. Scarlett Johannson would be my backup pick if she wasn't nominated in another category (Supporting Actress for Jojo Rabbit). I can see her splitting votes between herself. Cynthia Erivo for Harriet and Charlize Theron for Bombshell were both nominated despite muted reactions for their films. I don't see either of them stunning the world on February 9th. The only woman I see with a legitimate shot to take down the lead is Saoirse Ronan in Little Women. Just 25 years old, this is her fourth nomination. The Academy loves her and the reaction to Greta Gerwig missing out on the Best Director category created a bit of chaos in the film community. There's a lot of love for this movie—it has grossed nearly $150 million worldwide—and the Best Actress race has skewed younger over the past decade with wins for Jennifer Lawrence, Natalie Portman, and Emma Stone. I still see Zellwegger at the top, but if anyone is going to shock her, it's Ronan. She's +3300, so putting a few dollars down couldn't hurt.

Winner: Renée Zellweger, Judy (-3335)

If You Want to Make It Interesting: Saoirse Ronan, Little Women (+3300)

Now time for a little intermission!

Remember Invictus? We don't.

BEST SUPPORTING ACTOR

I can't remember a loaded category quite like this one, which includes Brad Pitt, Tom Hanks, Al Pacino, Joe Pesci, and Anthony Hopkins. It's a who's who of white men in Hollywood. With that said, this is the Academy's one chance to ensure a victory for Once Upon a Time...in Hollywood and the way that all of the preceding awards have been going, Pitt will win his first Oscar for acting in the coming weeks. Along with a tremendous performance in Quentin Tarantino's newest movie, this seems like a culmination award more than anything else. People just like Pitt and want to give him awards and he's been rewarding his devotees in spades.

It seems like every award show speech has been a trial run for Pitt with the zenith coming on Academy Awards night. I have very little doubt about this one, but if anyone were to crash Pitt's night, I see it being Tom Hanks. Pacino and Pesci are running for the same movie in The Irishman and Hopkins' performance in The Two Popes was raved about by critics, but less so by general audiences. Hanks is Mr. Dependable and has the star-power and name recognition across a diverse voting body that will keep him close in votes. People also just like Mister Rogers.

Winner: Brad Pitt, Once Upon a Time...in Hollywood (-3335)

If You Want to Make It Interesting: Tom Hanks, A Beautiful Day in the Neighborhood (+3300)

BEST SUPPORTING ACTRESS

The only woman that had the chance to stop the runaway train that is Laura Dern's Marriage Story eventual victory didn't even make the Academy's five-person field. On the release of Hustlers, Jennifer Lopez seemed to be a guarantee at nomination time and a heavy contender for the award, yet she was left off of the short-list. Like Pitt, this feels like a career summit moment for Dern as the other candidates all have heavy dings against them: Margot Robbie was in a disappointing film, Scarlett Johansson will have her votes split with her Best Actress candidacy and Florence Pugh (despite my shouting from various rooftops across New York for her consideration) is too much of a newcomer. The only individual I can see making some noise is Kathy Bates, who has already won a Best Actress award for Misery. The Academy Awards adores her and nominated her for the controversial Richard Jewell. She also has the best odds in a category, where I see her as a definitive second-in-command.

Winner: Laura Dern, Marriage Story (-3335)

If You Want to Make It Interesting: Kathy Bates, Richard Jewell (+5000)

BEST ORIGINAL SCREENPLAY

This may be the most wide-open of the eight major categories and it shows in the odds. There are three movies that all have legitimate shots to take home the gold and two a step behind that still have the adoration and guild-support to cross the finish line first. I've been going back and forth between Once Upon a Time...in Hollywood, Parasite and Marriage Story just while writing this sentence and I'm leaning towards Parasite. South Korea's first movie to be nominated at this ceremony garnered six this year and I think the voters are going to want to celebrate it outside of the International Feature Film category. If it doesn't win either Best Picture or Director, which I don't think it will, I see them giving it screenplay as a commendation. This category is usually viewed as the "cool one" that can nominate and give victories to more thought-provoking and less Oscarbaity material. Get Out and Her are both recent winners and unique films like The Lobster, Ex Machina and Nightcrawler have snuck in during the last decade.

Winner: Bong Joon Ho & Han Jin Won, Parasite (-167)

If You Want to Make It Interesting: Quentin Tarantino, Once Upon a Time...in Hollywood (+130)

BEST ADAPTED SCREENPLAY

The Greta Gerwig snub at Best Director feels like an opportunity for her to finally win her first Oscar. The outroar over her dismissal feels like a rallying cry in this category and Little Women has been leading in the odds game ever since. Since the category's inception in 1928, only seven women have won Best Adapted Screenplay and the Oscars voters' clear affection for Gerwig (nominating her for her first two features) makes me think that they want to reward her where they can. The fly in Little Women's ointment is Jojo Rabbit, the Nazi-dramedy that has been an award attraction since it won the top prize at the Toronto International Film Festival. The film, despite its insane "Hitler as an imaginary friend premise" is grounded and thoughtful enough to sway voters. I can easily see both films taking home the Oscar, but lean slightly towards Gerwig's due to Little Women's overwhelming success and quietly-intricate and complex script.

Winner: Greta Gerwig, Little Women (+160)

If You Want to Make It Less Interesting: Taika Waititi, Jojo Rabbit (-182)

If you've made it this far, thank you. I hope you (and I) win some money. I'm not going to break down my reasoning for the other 16 categories but here are my winners:

Best Animated Feature Film: Toy Story 4 (-200)

Best Cinematography: 1917 (-5000)

Best International Feature Film Parasite (-10000)

Best Production Design Once Upon a Time...in Hollywood (-230)

Best Original Score 1917 (+325)

Best Original Song "Love Me Again" from Rocketman (-1000)

Best Film Editing The Irishman (+600)

Best Documentary Feature American Factory (-250)

Best Animated Short Film Hair Love (-250)

Best Documentary: Short Subject Learning to Skateboard in a Warzone (-1667)

Best Live Action Short Film Brotherhood (-305)

Best Costume Design Little Women (-335)

Best Makeup & Hairstyling Bombshell (-1000)

Best Sound Editing 1917 (-278)

Best Sound Mixing 1917 (-250)

Best Visual Effects Avengers: Endgame (+250)