That doesn't necessarily mean they've been the movies you initially expected to win. But it does mean that once they won, you could construct a short, simple, cynical, reductive explanation as to why Hollywood might have chosen them.
Let's consider the past five:
2013 - 12 Years a Slave (political correctness)
2012 - Argo (Hollywood to the rescue!)
2011 - The Artist (classic Hollywood)
2010 - The King's Speech (classic Oscar bait)
2009 - The Hurt Locker (war movie)
You have to go back to Slumdog Millionaire in 2008 to find a movie that Oscar anointed simply because it was a "good movie." This isn't to say that Slumdog is better than those movies, just that you can't immediately summarize the thinking that made it the obvious choice to win, other than its quality. It has no other element that traditionally ensnares an awards body with a particular mindset and a particular tendency to congratulate itself. I'd argue that the two that came before are similarly unusual choices (No Country for Old Men and The Departed), and that you have to go back to Crash in 2005 to get another "typical" best picture winner (important social issue movie).
Well, it's possible that this year will kick off another three years of Oscar iconoclasm.
At this point in the season, you'd have to say that the race boils down to the two B's -- Boyhood and Birdman. The frontrunner had been Boyhood all along I think, but some recent significant wins have caused this website that devotes itself to handicapping the winners (http://www.ropeofsilicon.com/oscar-predictions/best-picture/) to anoint Birdman the new frontrunner.
And either would be a "weird" best picture winner indeed.
On the one hand you have a movie made over the course of 12 years, with virtually no input from Hollywood and featuring a handful of non-professional actors. It doesn't have a traditional narrative, narrative structure or catharsis, and on a technical level it is rather workmanlike. It is a contender primarily because it is believable, relatable and sneakily emotional. It created perhaps the year's most communally shared audience experience. But rarely do you see a movie that closely reproduces a realistic version of life in line for such accolades.
On the other hand you've got a movie that is cynically reducible to one crazy stylistic choice, which is to shoot the entire movie as though it were one shot. While this tends to get film geeks aflutter, it typically does not translate to the type of success with mainstream audiences that Birdman has enjoyed. It does have some classic Oscar credentials by being about the theater (which captures Oscar's desire to celebrate entertainment history) and by involving the redemption of a Hollywood actor (a little bit of the "Hollywood to the rescue" mentality of Argo). But canceling that out is the fact that it's about a guy who played a superhero, and has a title (an abbreviated title, anyway) that sounds like an actual superhero movie. No superhero movie has ever been nominated for best picture.
Either winner would be a celebration of some kind of landmark technical achievement. In fact, the way they were made has been an equal part of the conversation as what they are actually about. In Boyhood, the way it was made and its subject matter are intrinsically linked. In Birdman, they have nothing to do with each other. In both cases, you'd have to say that without the unusual technical approach to making them, they would not be nominated this year (though I do sometimes wonder how many of Birdman's viewers actually notice that there are no visible edits).
Like them or not, these are weird movies. They are made by filmmakers who were thinking way, way outside the box. In most years, both would be the consensus deserving choice that ended up losing to something like The Imitation Game. This year, one will win.
Having had both in my top ten, and one at my #1 spot, I'd honestly be happy to have either carry off the win, which is an unusual position to find myself in. Most years I have a favorite I'm clearly rooting for over a rival I don't find deserving, but not this year. Unless some more conventional movie makes a last gasp at contention, it'll be one of these two -- and I don't see The Imitation Game suddenly coming out of nowhere to seize the zeitgeist. (The Grand Budapest Hotel would also be a good unconventional choice, but I'd have to say it's a longshot at this point, despite tying for the most nominations.)
So what will happen?
If we are to further psychoanalyze Hollywood -- which is the premise this entire post is based on -- I'd have to say that Birdman will emerge. As unconventional as it is, it is definitely more conventional than Boyhood, in the sense of celebrating Hollywood and featuring actors it is time to honor (Michael Keaton has a significant edge over Ethan Hawke in that regard, though Patricia Arquette should definitely win in the best supporting actress category). And if you believe the narrative that the most critically acclaimed film of the year is the one that never wins best picture -- see examples like The Social Network and L.A. Confidential -- then that same fate could easily befall Boyhood.
The thing is, I don't get the sense that Boyhood's most ardent supporters consider whether it wins best picture to be any necessary measure, or perhaps even a desirable measure, of its success. They don't need to have that external validation of the emotional experience they had watching this movie. And even if they do secretly crave that external validation despite being unwilling to admit it, they will be satisfied with Arquette's win. And Richard Linklater seems the best bet to win best director whether his movie wins or not.
I said earlier that I didn't care which movie won, but I obviously did have one ranked higher than the other. Boyhood was only my #8 movie of the year, while Birdman took top honors. So I should be rooting for Birdman to win, right? I actually don't think I am, and here are three reasons:
1) A win for Boyhood would be a much-deserved recognition of the myriad ways Richard Linklater has been expanding our cinematic horizons over the course of his career. Boyhood is not an isolated experiment for Linklater. It is just the latest in a career defined by (mostly successful) experiments.
2) A win for Boyhood would celebrate the movie of the year. I would say Boyhood defined 2014 at the movies, whereas Birdman just happened to come out in 2014.
3) But perhaps most importantly, a win for Boyhood would be the choice that gave me the greatest reassurance that the system is not broken. A win for Boyhood would teach me that just when I thought I had gotten the Oscars all figured out, I had to go back and reconsider all my assumptions. A win for Boyhood would condition me to expect the unexpected in Oscar's future.
Also, it's just a damn fine movie.