How ‘Moonlight’ Pulled Off the Biggest, Wildest Oscars Upset Ever

Shocking as it was, the “Moonlight” victory made sense on a night full of wins that were both emotional and political

It was inevitable all season, from September all the way to Oscar night, and then all the way to the moment the producers from “La La Land” stood on the stage of the Academy Awards accepting the award for Best Picture.

And then, suddenly and shockingly, it wasn’t inevitable at all.

Warren Beatty had been given the wrong envelope, or had been given an envelope stuffed with the wrong card, the Oscars had descended into chaos and “Moonlight” had won the Academy Award for Best Picture.

“La La Land” was a prohibitive favorite coming into the night — a fun, audacious musical that ticked off all the boxes that are supposed to appeal to Oscar voters: It had the glamor of “The Artist” and the risk-taking of “Birdman,” and it was about Hollywood, which is Hollywood’s favorite subject.

But somewhere along the way to the coronation of Damien Chazelle’s musical, something else intruded, and “Moonlight” scored the biggest Oscar upset in decades, and then the wildest ending to an Oscar show ever.

The warning signs for “La La Land” had come early in the telecast. “Moonlight” won the first Oscar of the night, Mahershala Ali’s for Best Supporting Actor, and “La La Land” didn’t win its first award until an hour and 45 minutes into the show, after losing in one category in which it was favorite, Best Sound Mixing, and two in which it was supposed to have a strong chance of winning, Best Costume Design and Best Sound Editing.

But “La La Land” rallied late in the show, winning five of the last nine awards, including Best Director for Chazelle. So it made perfect sense when Warren Beatty opened the envelope and Faye Dunaway announced “La La Land” as the winner — except that it was a mistake, and one that shockingly wasn’t corrected until midway through the third “La La Land” acceptance speech.

(Two PricewaterhouseCoopers reps are stationed in the wings of the Oscar stage, with the winners memorized and instructions to stop the show if an incorrect name is ever announced.)

A month ago, in the aftermath of the “La La Land” victory at the all-important Producers Guild Awards, I wrote this: “As the atmosphere grows more charged and partisan, the chances grow that ‘La La Land’ could appear to be a light movie in serious times. Because of that, it might conceivably become a less appealing winner than ‘Moonlight,’ a drama about a young black gay man that could be seen as a statement in favor of tolerance and inclusion …. “

I didn’t expect that it would happen, but it did. And not just for political reasons, but for emotional ones. As dazzling as “La La Land” is, “Moonlight” was a deeply personal but deeply universal story about a search for identity, and it resonated across the spectrum.

So when the inevitable backlash began to grow around the front-runner, as it always does, “Moonlight” was uniquely positioned to take advantage of whatever qualms existed about “La La Land.”

It could also have been helped by the Academy’s preferential system of vote-counting in the Best Picture category, where a film ranked second or third on a large number of ballots could prevail over a more divisive movie.

And “Moonlight” could play the importance card. Look at last year’s race: The bravura filmmaking of “The Revenant” and the exuberant fun of “The Big Short” lost to the sober, meticulous filmmaking of “Spotlight,” which was seen as a more significant story. Or the race in 2013, when the dazzling cinematic achievement of “Gravity” lost to the weightier “12 Years a Slave.”

Oscar voters, it’s safe to say, like important movies. And as an intolerant administration took power in Washington and tried to exclude people, a film about tolerance and inclusion took on added weight and importance, until honoring it took precedence over saluting a vibrant musical.

The “Moonlight” victory felt in tune with much of the night, which contained a string of wins that were both emotional and political, from the “Moonlight” win for adapted screenplay to the documentary-feature victory for “O.J.: Made in America,” and the doc-short win for “The White Helmets.”

The voters, it seemed, were in a serious mood. And so, after the Oscar mess to end all Oscar messes, were the winners.