Ready for the 2020 Oscars? First, I gave you my picks. Now, I want to make you some money. Betting the Oscars is not a typical bet. It’s not like a sports bet where the result is determined live. Oscar bets are voted on by the Academy so essentially, we’re betting on how a group of people voted. It’s not easy, but there are some keys to look for while betting the 2020 Oscars.

  • Use Results From Other Award Shows As Guide – It’s very rare for an award winner to come out of nowhere. Usually, each category has one to three contenders. In most cases, these contenders won awards at major shows like the Golden Globes, SAGs, or BAFTAs. Furthermore, for technical awards, there are guild awards given out for crafts like writing, editing, and cinematography. The more awards won at the guilds, the better the chances of winning an Oscar.
  • Favorites Win A Lot – This doesn’t help when it comes to making money, but it does pay off to pick favorites if you are doing an Oscars pool where you have to pick winners without odds.
  • Look For Bets With The Best Value – The bets I’m suggesting to make are not “locks.” Most of them are underdogs and long shots. They may not win, but it’s your best chance of making money. Try to avoid categories where the favorite is significantly out of reach.
  • Bet At Your Own Risk – I’m not legally obligated to say this, but I’m going to say it anyway. Have fun, but be smart!

*Odds taken from Draftkings at 5:30 PM EST. Subject to change.

My picks do NOT reflect who I believe will win. They reflect the best bet you can make to win the most money.

Best Picture

DK Best Picture 2020

Great value here for the top three spots. 1917 is the favorite because of Best Picture wins at the Golden Globes, BAFTAs, and PGAs. Right on its tail is Parasite, which won the Best Ensemble Award at the SAGs and will win Best International Feature Film. My pick is 1917 because the PGA winner has won 8 of the last 10 Best Pictures at the Oscars. Plus, it has great odds for a frontrunner. I’d bet on both 1917 and Parasite. If you have extra money to blow, sprinkle a little cash on Once Upon a Time in Hollywood. The Academy loves Tarantino and they love movies about Hollywood. 10 to 1 odds make for a great payout.

Bets To Make: 1917 in Best Picture -125 and/or Parasite in Best Picture +150

Every Acting Category

Do you like lighting your money on fire? If so, then you’ll love betting on the acting categories. I’m trying to make a case for any actor not named Renée Zellweger, Joaquin Phoenix, Brad Pitt, and Laura Dern, but I can’t do it with a straight face. All four actors are heavy favorites and have few losses on their resumes this season. Even though I don’t believe this will happen, if I had to pick one upset, it would be Scarlett Johansson in Best Actress. I can’t advise anyone to place a bet on an underdog in any of these categories, but Scar Jo in Marriage Story would be my play.

Bet To Make: Scarlett Johansson in Best Actress +1000

Best Original Screenplay And Best Adapted Screenplay

Two categories, two underdogs that have legitimate shots at winning. Let’s start with original screenplay. Parasite is the favorite because of wins at the WGAs and BAFTAs. However, right on Director Bong’s heels is Mr. Quentin Tarantino. You can never count out Tarantino in the original screenplay category because of his two previous wins for Pulp Fiction and Django Unchained. I would never blame someone for betting on Tarantino. In adapted screenplay, Jojo Rabbit also picked up wins at the WGA and BAFTAs. However, Greta Gerwig wrote the best adaptation of Little Women to date. Do not count her out, but Taika Waititi and Jojo is the best bet to make.

Bets To Make: Once Upon a Time in Hollywood in Best Orginal Screenplay +150 // Jojo Rabbit in Best Adapted Screenplay -177

Best Sound Editing And Best Sound Mixing

DK sound editing mixing Oscars 2020

The 1917 domino starts in the technical categories. If it wins in both sound editing and sound mixing, then 1917 is due for a huge night. That’s a possibility that may end up happening. However, for betting, Ford v Ferrari as a slight underdog in both categories is juicy. Ford v Ferrari is a very loud and effective film. If I had to choose which category Ford v Ferrari will win, I’m going with sound mixing.

Bet To Make: Ford v Ferrari in Best Sound Mixing +125

What are your best bets for the 2020 Oscars? Leave your thoughts in the comments or tweet us, @unafraidshow.

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