How did Moonlight win the Best Picture Oscar, when La La Land was not only the strong favorite going in to the evening, but also picked up Best Director? The answer has nothing to do with misadventures surrounding envelopes, and everything to do with the arcane subject of voting systems.
The default mode for “Oscar Movies” is, and always will be, Serious Drama. There are many exceptions, of course, but the overwhelming majority of Best Picture winners are the kind of movies which are considered a Drama by the Golden Globes, rather than a Musical or Comedy. When push comes to shove, musicals and comedies are generally considered lightweight, while the Academy loves to give the Best Picture award to a heavyweight movie.
Against that, of course, is the fact that La La Land is the kind of movie which is almost clinically designed to appeal to nostalgic movie-lovers of a certain age. If you believe in the Magic of Cinema, if you worship Singing in the Rain, if you can’t get that soundtrack out of your head, then La La Land is a breath of fresh air amidst all the dark and depressing fellow nominees like Manchester by the Sea, or Hacksaw Ridge, or, yes, Moonlight.
Thus were the battle lines drawn going in to the voting, in both the Best Director and the Best Picture races. Except there is one enormous and crucial distinction between the two. The Best Director race is first-past-the-post: Whichever director gets the most votes, wins. The Best Picture race, by contrast, uses a single-transferrable-vote system.
Damien Chazelle won the Best Director award for La La Land, getting more votes than Moonlight’s Barry Jenkins. (It’s worth noting that two years ago, when Chazelle’s Whiplash was in the running for Best Picture, it wasn’t even nominated for Best Director.) Still, in a five-way race, it’s highly unlikely that Chazelle got an outright majority of the votes.
It’s highly likely that the Best Picture race turned out the same way – that La La Land got more first-round votes than any other picture, with Moonlight coming in second. But this was a nine-way race decided by single transferrable vote, so the first-round outcome, while interesting, is far from decisive.
In the Best Picture voting, the first-round winner is much less important than the broad consensus. A lot of people loved La La Land; a lot of people hated it, too. So while it surely did very well in the first couple of rounds of voting, it simply lacked the staying power needed to win.
Basically, given the single-transferable-vote system, the thing which mattered is what happened to the votes for pictures like Manchester by the Sea. If that was your favorite movie of the year, or if you originally voted for, say, Fences, then there’s no way that you will have ranked La La Land above Moonlight. As the list got shorter and shorter, then, the vast majority of the votes which originally went to other movies ended up being cast for Moonlight, while La La Land picked up many fewer.
Hence the result: La La Land got a plurality of the votes, but Serious Dramas got a majority. When that happens, La La Land will win a prize like Best Director which is decided in the first round, but, happily for Moonlight, it will lose out for Best Picture.