Oscar predictions are for wimps. Sure, your usual fancy-pants film critics have lots of big talk about who they think will win, but if they’re wrong, what do they lose? A big fat nothing.
I, however, am a dangerous man. I live life on the edge. I’m not just talking about who I think will win the Oscars: I’m betting on it.

I wasn’t always so reckless. As a law-abiding citizen, when I lived in jurisdictions where gambling was illegal, I wouldn’t even put money into an office Oscar pool. Of course, it’s the virtuous ones who fall hardest, and so last year, when we moved to the UK where the gambling laws are looser, I went absolutely crazy. I bet (and I shudder to think of it) a full £10 on the Oscars. Yes, I know–it was wildly risky, and I lost £3 when Martin Scorcese lost Best Director. Then, when The Pianist failed to win Best Picture, I lost £4 more. (As a side note, a week earlier, I had had a moment of moral ambivalence when I left the screening of The Pianist and thought, “That’s a remarkably powerful picture–a true testament to the human will to survive. I better go put a few quid on it.”)
But earlier in the evening, Adrian Brody had taken home Best Actor, and my £3 bet on him blossomed into a stunning £27. I was a rich man–but high-rollers like myself aren’t satisfied with a single big haul. So this year, I am betting not merely £10 but a full £16.
In short, those of a nervous disposition or weak heart might want to leave the room before reading the rest of this dispatch.
This year, I don’t see an obviously under-valued winner, like I did last year when most punters were betting against The Pianist winning anything. The odds-on favorite is The Lord Of The Rings: The Return Of The Kings. I think it is indeed the most likely win–but I think the odds aren’t quite as strikingly in its favor as the bookies seem to think.
My theory is that is that the Academy tends to reward movies that you can feel just a little bit superior for liking. If you liked Shakespeare In Love, for example, you can feel smart for really liking something that was all about Shakespeare. If you liked A Beautiful Mind, you can feel smart for having completely understood a movie that was all about a supergenius. The question is, is Return Of The Kings a feel-superior movie? That depends on whether the Academy’s collective consciousness classifies it as “an adaptation of an important literary classic” or “a big fantasy action movie.” There’s a good chance the Academy will see it as the former.
(Note that I’m not making a claim about the psychology of any single voter. As any game theoretician can tell you, a collection of perfectly rational individual behaviors can give rise to a far less rational-seeming macrobehavior. Any generalizations I make are aimed solely at the Academy’s emergent group-mind. By contrast, its individual members all possess a passion for the cinematic art, a commitment to judging each nominee solely on its merits, and an ability to someday stumble across this essay at exactly the moment they’re considering casting a vote for me. Did I mention that they’re all snappy dressers, too?)
In any event, each year there is at least one big surprise winner amongst the major categories. In each category, I’m therefore betting on the most likely spoilers.
For Best Picture, I’ve bet £2 at 50-to-1 odds on Seabiscuit (which is feel-superior because it’s a historical drama about a simpler time); $3 on Master & Commander at 33 to 1 (feel-superior because it’s a seafaring costume drama); and £3 on the likeliest spoiler of them all, Lost In Translation, at 12 to 1 (feel-superior because it’s all artsy and stuff).
For Best Actress, it’s £1 on Whale Rider‘s Keisha Castle-Hughes, at 12 to 1. For one thing, she stars in a film that lets the viewer feel superior to the old-fashioned sexists who stand in her way. For another, she was just so fantastic, at such a young age, that she just might win.
In the same category, I also wagered £1 on Naomi Watts at 11 to 1, and £1 on Diane Keaton at 6 to 1. There’s an alternate theory of Oscar prediction that says it’s all about whose turn it is, and Watts and Keaton have both given remarkable performances in the past that didn’t get them Oscars.
For Best Supporting Actor, I put £1 each on Benicio Del Toro and Ken Watanabe. For Best Supporting Actress, I’ve put £1 on Shoreh Aghdashloo at 8 to 1, and £1 on Marcia Gay Harden at 20 to 1.
I wish I could bet on Best Original Screenplay, because I’m 99% certain that Lost In Translation will take home the Pulp Fiction Memorial “We Don’t Know What Other Award To Give You So We’re Giving You Best Screenplay” award. And Triplets of Belleville is a lock on Best Animated Feature; you can only vote in that category if you’ve seen all three nominees, which means the voters are likely to be die-hard animated film buffs who will dig Belleville’s unique visual world.
So good luck to all the nominees, and remember: it’s not about whether you win or lose. It’s about whether I win or lose by betting on you.