I’ve won money on the Oscars for four years straight. Let me tell you how it’s done.
Cynically. That’s the first and most important element. Stop reading now if you’re looking for insights into film-making, or acting, or virtuosity on the silver screen. None of that bullshit here. Just cold hard calculation.
It is better if you don’t see the movies. Let me repeat: when gambling on the Oscars, it works in your favour to not have seen the films in question. When you bet money, sentimentality is put to one side. Your subjective opinion is irrelevant. There is no deserving in gambling, and by god there is no deserving when it comes to the Oscars, if the results are anything to go by.
The only time I lose money on the Oscars (or to be precise, lose some individual bets – I’ve 
never actually lost money on the event as a whole) is when I bet on what deserves to win. Exhibit A: Mad Max Fury Road, which won 6 Oscars, but none of the majors (film, director, cinematography) which it self-evidently deserved.
Certainly more than, what bullshit beat it that year? Spotlight? The Revenant? Good lord.
The criteria for picking winners at the Oscars are as follows: perceived quality, hugs, and politics. Not in that order.
Perceived quality I don’t need to explain, other than to say if Rotten Tomatoes rates it and the luvvies on twitter rave about it, then it has sufficient quality.
‘Hugs’ is the expression I heard an Hollywood insider use, referring to the ground game of advocacy around the awards. Apparently, winning an Oscar is akin to winning a political campaign. Really good campaigns can help turn an Oscar in one’s favour, and selective leaks of dirt against other front runners can kill their chances.
For example, Eddie Redmayne (Theory of Everything) apparently charmed the voters so thoroughly he stole the prize from Michael Keaton (Birdman). Russell Crowe had won every lead-up award to the Oscars (BAFTA, Golden Globe, Screen Actors Guild, etc.) for A Beautiful Mind, but threw a phone at someone’s head, so didn’t win the big one. Spotlight’s victory was, in part, based on a lavishly funded ground game.
Politics. Well. Here’s the thing. The voters aren’t you or I. The voters are limousine liberals living in Hollywood. They are the one per cent. When betting on the Oscars, you have to put yourself in their shoes. The question is not: what’s the best movie? The 
question is: what does a fatuous American living in Los Angeles, with a limited grasp of the real world, think is the best movie? Sometimes these align with reality, mostly it aligns with a political moment.
So winning money on the Oscars is an attitude and a formula. The attitude is: 1) don’t watch the movie, 2) think like a limousine liberal, and 3) listen to the insiders.
The formula: Perceived quality + plus hugs + plus politics = Oscar.
See, I told you this was cynical.
The bets:
I didn’t have the time or the guts to put my bets up beforehand. I’ll take the plunge next year. The size of the bets will appear timid and insignificant to regular gamblers; non-gamblers tend to be gobsmacked when I tell them I’ve spent money on such an unseemly activity.
As they readjust their two hundred dollar vintage t-shirt and tuck into a fifty dollar breakfast of smashed avocado, quince, and a macchiato.
“Such a waste, Tim,” they say, as they distractedly glance at their thousand dollar iPhone X, wondering if their blog post extolling the virtues of Porg cosplay has received any hits.
I made 22 bets totalling 248.50. Broadly, they were in three categories: favourites, good bets on longshots, and bad bets on longshots.
Favourites:
- Blade Runner 2049 – Cinematography $50 @ $1.30 = Win $65
This was betting with my opinion, sure – because the cinematography in Blade Runner 2049 was brilliant – but it was also political. Roger Deakins had been nominated 13 times for this award and never won. He was favourite. It was his time.
- Blade Runner 2049 – Visual Effects 42.20 @ $1.72 = Win $72.60
This was also betting with my opinion. Blade Runner 2049 was slight favourite, though of course I hadn’t seen any of the other nominated films (except Star Wars: The Last Jedi, which deserves to win nothing but a place in the dust bin of history). But there was no political reason to vote for any of the others, so I went with my heart.
- Get Out – Screenplay 20 @ 3.5 = Win $70
Get Out had an excellent, highly original screenplay. In fact, the way Jordan Peele managed to show white liberals acting weird towards a token black person could be exactly the way they’d behave if they were planning to remove that black person’s brain in order to take possession of their body. Well, actually, that was genius.
But that’s not the point, is it? The point is, Get Out has the right politics, in addition to quality. I put money on it when it was behind two other films (Three Billboards and Shape of Water), but it soon narrowed to favourite. This was my favourite bet of the lot.
- Double Bet – Three Billboards (best picture), Del Toro (Best director). $15 @ 2.1 = Lose
Most of the predictions were bending toward another split between director and best film. I thought a compromise might be in the voter’s minds. Wrong, but I don’t dislike this bet.
- Shape of Water – 3 Oscars. $10 @ 2.37 Lose
It won four, in the end. It seemed to me there were a few different ways The Shape Of Water to get to three. Again I don’t hate the bet, but the odds were never great, so the bet was marginal.
Good longshots:
- Double Bet: Three Billboards (best picture), Chamalet (Best Actor). $8.30 @31 = lose
While Gary Oldman was overwhelming favourite, there were some negative stories about him bubbling along in the background, and Timothée Chamalet apparently had a great ground game. At 30 to 1 I don’t mind this bet at all.
- Double Bet: Shape of Water (best picture), Chamalet (best actor). $5 @ 41 = lose
Some reasoning as above, covering my best picture bases.
- Animated Short: Garden Party. $10 @ 6 = Lose
- Documentary Short: Heaven is a Traffic Jam on the 405. $10 @ 8 = Win $80
- Live Action Short: Silent Child. $10 @ 4.33 = Win 43.3
For Garden Party, Heaven is a Traffic Jam on the 405, and Silent Child, I based my bets on an insider’s picks, one who had a habit of getting these correct. None were favourites, either, which I liked. He scored me 2 from 3. Apparently, Academy Voters often don’t watch these, and often bet based on whether they like the title. For example, the 405 is, I’m told, a highway in L.A., which made it an easy pick.
- Film: Ladybird – 6 @ 11 = Lose
- Film: Get Out – 5 @ 15 = Lose
Covering bets just in case the academy decided to go excessively political.
- Double: Film – Shape of Water / Screenplay – Get Out. $9 @5.5 = Win $49.5
I had a good feeling about this bet.
- Acceptance speech (any actor): 3:01 – 4:00 / 10 @3:00 = lose
- Acceptance speech (any actor): 2:01 – 3:00 / 15 @4.33 = Win $64.95
- Acceptance speech (any actor): 1:01 – 2:00 / 5 @6.5 = lose
Like many novelty bets at the Oscars, the company setting the odds had no idea. You get this in politics and entertainment – two areas where the major betting agencies aren’t really investing a lot of their intellectual energy.
Example: a couple of years back twitter was going nuts with the #OscarsSoWhite campaign, and Chris Rock was hosting. There was a bet on his first joke. There were a dozen or so choices over what that joke would be.
The options of ‘black people’ and ‘white people’ where there, both at 15 to 1. Now, of course Chris Rock is going to open his monologue with a joke about one of those two. Of course. And he did. And I got paid.
Last year, Leonardo De Caprio had the longest speech, and that was 2 minutes 20 seconds. I was confident it would come in around this time frame again, but put some safety bets on either side (I’m not sure if the latter is smart or dumb, I don’t bet often enough to know whether professional gamblers would do the same).
Gary fucking Oldman made it close though. Umm and ahh-ed all the way to 2 minutes 58 seconds.
Bad (in retrospect) bets:
- Megabet: British bet (Film – Dunkirk, Director – Nolan, Actress – Hawkins, Actor – Oldman)
@5 @126
This was never going to win, But it was risking 5 bucks for over 600, and I couldn’t help myself. 
- Dunkirk: Film – $10 @ 26 = Lose
Never going to win, but I’m a sucker for long shots. Oh, and Dunkirk was the best film I watched last year (outside of Blade Runner 2049), which, as I keep saying, is irrelevant.
- Nolan: Director – 5 @3.5 = Lose
Made the mistake of betting with my honest opinion here.
- Dafoe: Supporting Actor – 5 @4.5 = Lose
I made this bet before I realised how strong a favourite was Sam Rockwell – who apparently is also widely admired in Hollywood as a nice guy to work with. Still, at five bucks, not terrible.
Total bet: 248.50
Total won: 449.09
I didn’t watch the Oscars. As a rule I don’t enjoy moral lectures from vacuous multimillionaires. My toddler likes ABC for Kids, and I much prefer taking my morality from Sesame Street or Dirt Girl World.
In terms of winning money it is particularly efficient: I don’t have to watch the movies or the ceremony, and I bring home the Benjamins. Well, two, anyway.
Don’t ever change, Hollywood.
I am not a movie review Writer but this article is really entertaining