Winning Your Oscar Pool in Three Easy Steps

Friend of the site and all around great person Claire McBroom has graced Backlog with her presence, bringing you, dear reader, surefire steps to winning your Oscar pool. Personally, I plan on picking ‘Mad Max: Fury Road’ for everything. I think it is a sound strategy. – Will 

A few years ago, some of my most pop culture-obsessed friends and I started a yearly Oscar pool. None of us are professional entertainment or show biz types, and the stakes are low, but the thrill of the win is an incomparable high.

I should know — I’ve won more pools than any of my friends. I’m not bragging, this is just a statistical fact.

Ok, maybe I am bragging. It feels great.There are lots of reasons why the Oscars don’t actually matter, in the same way that sports don’t actually matter, except to the people who stand to win and make additional millions on top of the millions they already make. Additionally, there’s been a recent cultural meta-narrative examining the relevance of the Oscars, particularly around questions of women and race.


In 86 years of existence, only four female directors have been nominated for an Oscar, and only one — Kathryn Bigelow — has won. Similarly, the ceremony that will be held in 2016 holds the dubious distinction of being the second in a row in which no actors or directors of color are nominated for an award. When the nominations were announced last week, the hashtag #OscarsSoWhite started trending on Twitter within just a few hours.

So, it’s in the spirit that the Oscars really don’t matter, especially given the mostly white, mostly old, mostly male academy, that I reflect on my strategies for winning my yearly Oscar pool.

My goal is that readers might become more savvy awards-season watchers once they start decoding the elaborate dance that goes into securing nominations and awards. There was a time in the not-so-distant past when nobody outside Hollywood was really paying attention to the Oscars.

Today, there’s a cottage industry built around red-carpet watching and Oscar parties, not to mention the fact that ticket sales from films released in that awards sweet spot around the holidays stand to grow from increased exposure. Here’s hoping that if we pay attention and keep watching and commenting and demanding more from our entertainment, the Academy might take notice and change with us.

Or, more realistically, you can pick up some tips and destroy your friends at this year’s Oscar watch party, securing a year of bragging rights. Either way, I’m here to lend a hand. Here are three steps that can help you make smart choices and win this year’s Oscar pool.

Step One: Forget What You Like

I think one of the biggest slip-ups people can make when predicting Oscar winners is choosing actors or films they personally loved, or choosing what they think is objectively the best. If you don’t really want to win an Oscar pool, this is a totally acceptable and fine approach, and you are a beautiful human being. If you want to win, though, you need to separate who should win from who will win.

The Oscars are not about rewarding the objective best, despite all the “bests” you hear in the category names. Rather, they are a highly calculated and complicated mating-ritual between industry insiders and the faces and names we see on the screen, and you have the best shot at getting more predictions right of you choose with your head and not with your heart.

You, transforming into a well-trained, Oscar-picking machine.

Step Two: Know Which Awards (Kind Of) Matter

If you caught this year’s Golden Globe Awards a few weekends ago, you might have picked up on a theme that united most of host Ricky Gervais’s jokes: the Golden Globes REALLY don’t matter.

Tina and Amy also poked gently at the Hollywood Foreign Press Association over the past few years, pointing out that the Golden Globes are little more than an excuse to watch TV stars and movie stars get drunk and mingle in nice clothes.


Beyond their general silliness, though, the Globes are also a pretty bad indicator of who will take home an Oscar later in the season. I don’t believe in copying my picks wholesale from someone else’s list — where’s the fun in that? — but knowing which pre-Oscars awards shows are indicative of which films and actors have the best shot at winning on the big night is a pretty substantial factor in “choosing with your head.”

My general rule of thumb? The Golden Globes, though splashy, simply don’t matter. Nate Silver and his stats nerds over at FiveThirtyEight have crunched the numbers to show that there’s between a 48-49% win rate transferable from the Globes to the Oscars in recent years.

You have much better odds of making correct choices for big awards like Best Picture and Best Director if you pay attention to the considerably less flashy industry guild awards from the Directors Guild of America, the Producers Guild of American, and the Screen Actors Guild.

Step Three: Follow the Gossip

Increasing your number of correct Oscar predictions means you have to develop a familiarity with the gossip engine that powers the awards-season machine. Perhaps the best way to do this is knowing which nominees are actively campaigning for an Oscar, hiring awards consultants and being overly-visible by showing up to the most parties, events, etc.

Many winners of past Oscars have prevailed due in large part to aggressive campaigns. See: the ubiquity of Eddie Redmayne, Anne Hathaway, and Natalie Portman and their subsequent wins in recent years. This year, the most visible campaigner is definitely Leonardo DiCaprio, who many — myself included — believe will win the award for Best Actor at this year’s ceremony.

Leo’s almost guaranteed win has nothing to do with his performance in The Revenant. Rather, Leo will win on the strength of his campaign and the huge amount of money that’s fueling it, as The Wrap reported as early as October.


I don’t think it’s a stretch to assume that a recent resurgence in “Leo’s never won an Oscar” memes could be a benefit of hiring “every awards consultant known to man.” It’s worth noting that some awards campaigns can draw criticism, like Melissa Leo’s infamous “Consider…” ads in 2011.

Melissa Leo, though, went on to win her Oscar, proving that an aggressive campaign is more often than not unbeatable.

So, as you start to make your choices for this year’s Oscars, keep these tips in mind. Stay tuned to Backlog Adventures for additional Oscar info, tips for crafting the rules to your pool, some instances when choosing with your heart can be the correct option, and my picks before the big night.

Claire McBroom just wants to be included. She lives in Cleveland, OH. Find her on Twitter @cmcbroo or @MomsWatchAwards.

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