Predicting the Oscar Races You Care About


Armed with self-proclaimed expertise and too much free time, we at GWW love the Oscars and the discussions they generate. There are some inherent flaws in labeling movies as “Best,” but nevertheless we get to have debates about great movies and get exposure to a variety of incredible performances. This year, Oscar night presents an odd mix of close races and surefire picks, with a wonderful array of A-List names and talented rising stars. My “expertise” does not extend into the tiny categories that will surely ruin your picks sheet, so I’ll stick to the bigger categories. I’ll give Who Should Win and Who Will Win for each category, though in some cases this may be the same film or performance.

Best Actor
Should Win: Matthew McConaughey, Dallas Buyers Club
Will Win: McConaughey


All five nominees have had much praise bestowed upon them, though Christian Bale and Bruce Dern have not seriously entered the race. Leonardo DiCaprio seems destined to win a couple of these eventually, but I don’t see his Wolf of Wall Street performance and career accomplishments overtaking McConaughey’s haunting depiction of a man battling AIDS and his own prejudices. 12 Years a Slave‘s Chiwetel Ejifor seems to be the most likely man to unseat McConaughey, but I don’t think it will happen. I see Steve McQueen’s triumph being rewarded as a larger work, though it does contain numerous fantastic performances. In short, I’ll be surprised to if we don’t get to hear some “Alright, Alright, Alright” on Sunday night.

Gaunt haunts.

Best Actress
Should Win: Cate Blanchett, Blue Jasmine
Will Win: Blanchett



I mentioned that some races are not too close this time around, and this is one of them. McConaughey is not really a sure thing, but Blanchett seems to be. I think it’s safe to assume Woody Allen’s creepiness won’t affect Blanchett bringing home a statuette, though she will emerge from an incredible list of nominees. You can pretty much pencil in Judi Dench and Meryl Streep every year at this point, and Amy Adams is quickly racking up a remarkable run of Oscar nominations, now with FIVE nominations in the last nine years. She’ll be back for some time to come, and Sandra Bullock already got her (undeserved) Oscar. Blanchett has been cleaning up on the awards circuit, and every sign points towards her leaving with a first leading actress win.

Stop crying, Cate, you’re going to win!

Best Director


Should Win: Alfonso Cuaron, Gravity 

Will Win: Cuaron


Director is a fascinating category this year, filled with the big, Oscar-bait names of Scorsese, Russell, and Payne but with all indications suggesting a showdown between Cuaron’s stunning visual work and Steve McQueen’s heartbreaking 12 Years a Slave. I hope as many voters as possible got to see Gravity on a big screen, though the movie certainly wows regardless. I see McQueen’s work getting some love in other categories (don’t read ahead!), but here Cuaron’s innovation and exploration will prevail.

“No. No, Alfonso. I’m not gunna pull it.”

Best Original Screenplay


Should Win: Her, Spike Jonze

Will Win: American Hustle, Eric Warren Singer and David O. Russell


Jonze’s unique work has earned the big writing prizes at many pre-Oscar shows, including the Golden Globes, but I fear it will get Hustled (pause for laughter) out of the Oscar. This would not be a great tragedy, as Russell and Singer did produce a wonderful script, even if it has led to a somewhat overrated film in my estimation. Dallas Buyers Club will not win here but does deserve a tip of the cap. Also of note, Woody Allen is nominated for Blue Jasmine, but I am pretty sure the chances of him winning are less than those of ___________ (You be the comedian for this one). Both Her and Hustle boast strong scripts, though I wish I could predict a victory for the delightful Jonze. As least he has this.

He’s so normal when captured in stills…

Best Adapted Screenplay


Should Win: 12 Years a Slave, John Ridley

Will Win: 12 Years a Slave


There seems to be a certain level of consensus for this one, with many experts and critics pointing towards Ridley’s work as both deserving and a reward for some voters who did not give the film the nod for Director, Picture, or both. I would like to see The Wolf of Wall Street get a little more credit here, but it’s tough to argue Ridley deserving to take this one home.

Ridley’s script helped several actors produce breathtaking performances.

Best Supporting Actor


Should Win: Jared Leto, Dallas Buyers Club

Will Win: Leto


I must admit Buyers is one of the nominated films I saw most recently, so there may be some recency effect at play, but I think this is the clearest pick of the night. This should be a gimme on your scorecard, as Leto gives one of the more memorable performances in recent years. It probably helps that he’s sort of a crazy person, but Leto reaches a level that solid nominees like Jonah Hill and Bradley Cooper do not, through no fault of their own. This category has many great roles, but Leto should win running away.

Not helping the cause of anti-eating disorder groups, Jared, by going out and winning Oscars.

Best Supporting Actress


Should Win: Lupita Nyong’o, 12 Years a Slave

Will Win: Jennifer Lawrence, American Hustle


I came to these answers through a very scientific coin flip. I see these two ladies as breaking away from the rest of the pack, but from there it’s a tossup. There are those who will shy away from Lawrence because of her victory last year as Best Actress, but I still see her prevailing. Nyong’o seems destined for big things after this impressive performance, but I see Lawrence edging her out for a second straight year with a trophy. Really, though, this race is too close to call. I’m confident in the winner being one of these two, but that’s where the confidence abruptly ends.

Irrelevant? Irrelevant!

Best Animated Feature


Should Win: Frozen

Will Win: Frozen


Despicable Me 2 entertained, and The Wind Rises sent a Miyazaki message, but Frozen seems like a near-lock to give Disney its first ever win for this category (which sounds odd but is, in fact, the case). I have no beef with Frozen here, as the movie entertains on its own and has led to hilarious internet fun. If you watch the movie, good luck getting “Do You Want to Build a Snowman” out of your head. Frozen will not resonate on the level of something like Up, but Disney’s film makes for a solid BAF winner.

I love Olaf.



Best Picture


Should Win: 12 Years a Slave

Will Win: 12 Years a Slave


I appreciate all of the nominees, but time and space are limited, so we’ll focus on just a few. I personally loved The Wolf of Wall Street and Dallas Buyers Club, but found American Hustle to be lacking in cohesion and stability. At the risk of being boring, I don’t see any shockers sneaking into the contention here, as all we’ve heard is a battle between 12 Years a Slave and Gravity. We’ll probably enjoy watching Wolf or Hustle more as time wears on, but McQueen and Cuaron accomplished more than anyone else this year. It can sometimes be difficult to distinguish why a film earns a Directing win but not the night’s big prize, but this year Cuaron does seem to have earned the former despite McQueen’s fuller, richer work. Call it whatever you like — boring, predictable, repetitive — but I expect to see McQueen smiling from ear to ear to end the night, and I’ll be satisfied, and so will he…maybe.
Please note: We hold no responsibility for the success or failure of your Oscar picks. If you win, however, remember where you came from.
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About Author: Brian McMahon

Brian is an author and co-founder of GoodWillWatching. He likes to write and is deathly afraid of bugs. His Great American Novel, not yet titled or existent, will be shocking the world some time or another. He once stayed up for two days straight because of poor information regarding the arrival of Halley’s Comet, which was not due for approximately 57 years. You can follow him @bm1313 on Twitter, or in real life from a safe distance.