So here is a dumb little exercise I decided to tackle for no reason. Following the end of the Oscars on Sunday, I started to look back on the Best Picture winners of recent years. And, honestly, I was pleasantly surprised. As much as we like to complain about the movies that win Academy Awards, the truth is that the winners are rarely genuinely bad. If anything, we get angry because they choose the wrong kind of good movie, consistently showing affection for solid, inoffensive, B-plus material while passing by more ambitious, bolder fare. Anyway, for kicks and giggles, I decided to rank every Best Picture winner since the turn of the century, explain my verdict, and then provide my choice for the nominee that should have won that year. I’ve also decided to divide the winners into three tiers: the years when the Academy chose well, the years when the Academy chose a good movie instead of a great one, and the years where they just plain blew it. Now, let’s get started.
Great Job, Academy!

1) The Departed (2006)
The challengers: Babel, Letters from Iwo Jima, Little Miss Sunshine, The Queen
The winner: This might be a somewhat controversial number one, since many seem to think of The Departed as a weaker Martin Scorsese film and that it only won the Picture and Director awards because he hadn’t before. Hogwash, says I. The Departed is one of my favorite Scorsese films, an entertaining and cynical crime epic about a town that revolves around one crime boss (Jack Nicholson) and two men (Matt Damon and Leonardo DiCaprio) who find themselves trapped on sides of the law where they don’t belong (or maybe they do). Admittedly, my love of this movie may be due in part to my age when I saw it, and it was something of a Scorsese gateway drug early in my movie loving career. If it was the 10th movie of his that I saw, would I love it as much? Maybe not, but as it stands, it will forever hold a special place in my heart.
Who should have won: Nailed it!

2) No Country for Old Men (2007)
The challengers: Atonement, Juno, Michael Clayton, There Will Be Blood
The winner: In hindsight, this is a fairly unusual Best Picture winner by modern Academy standards. On a plot level, it’s a pretty standard suspense thriller, and it all leads up to an impossibly bleak and deliberately unsatisfying ending. However, not even the Oscars could ignore a film as impeccably crafted as this. This may go down as one of the most agonizingly tense films of the 21st century, and every scene feels as though it has the potential to end in bloodshed. (They often do.) This is thanks to the Coen brothers’ typically chilly tone, which has never been used to greater effect, and a legendary performance by Javier Bardem in the role of Anton Chigurh.
Who should have won: As great as No Country is, Paul Thomas Anderson’s There Will Be Blood is every bit as good, if not better. Even so, that’s not me saying that it should have won over the Coens’ film, but it would have been just as deserving. So, either way, it’s hard to give this winner anything but a thumbs up. 2007 was a pretty good year.

3) 12 Years a Slave (2013)
The challengers: American Hustle, Captain Phillips, Dallas Buyers Club, Gravity, Her, Nebraska, Philomena, The Wolf of Wall Street
The winner: Every once in a while, the obvious Best Picture choice turns out to be the correct one. Such was the case last year, when Steve McQueen’s towering 12 Years a Slave entered the Oscar race in pole position, was able to hold off surges from the likes of American Hustle and Gravity, and ultimately came away with the top prize. If only things like this always went according to plan.
Who should have won: Nailed it! (Yes, you may recall I technically placed The Wolf of Wall Street higher on my end-of-the-year list. But 12 Years was much more deserving of this award. Don’t ask me to explain my logic.)

4) The Lord of the Rings: The Return of the King (2004)
The challengers: Lost in Translation, Master and Commander: The Far Side of the World, Mystic River, Seabiscuit
The winner: This year was another instance of the Academy bending their preferences to honor a filmmaking achievement that could not be overlooked. The first two installments in Peter Jackson’s spectacular Lord of the Rings trilogy were both nominated for Best Picture, and with the third and final chapter, the Academy decided to shower Jackson and his crew with nonstop love. The Return of the King came out the ceremony with a staggering 11 wins, and there’s no question the Academy was awarding the entire trilogy more than they were this final chapter by itself. As disappointing as the Hobbit trilogy may have been, the whole Lord of the Rings saga remains one of the great accomplishments in cinematic history, and it should be remembered as such.
Who should have won: Nailed it!

5) The Hurt Locker (2009)
The challengers: Avatar, The Blind Side, District 9, An Education, Inglourious Basterds, Precious, A Serious Man, Up, Up in the Air
The winner: This was the first year in which the Academy jumped to 10 nominees, and it’s hard to be sure exactly what effect that had on the final result. This also turned out to be one of the more intriguing races in recent memory; a battle between James Cameron’s record-shattering, $250 million sci-fi colossus Avatar and Kathryn Bigelow’s $15 million psychological war drama The Hurt Locker, starring some no-name punk named Jeremy Renner. In a rather stunning turn, Bigelow’s film came out of the ceremony the big winner, and it’s a rare case of the Academy choosing to rally behind the little guy as opposed to the ultra-successful behemoth.
Who should have won: The Hurt Locker is swell, but the best movie to come out of 2009 was Quentin Tarantino’s Inglourious Basterds. I am one of the few that believes Basterds might be Tarantino’s best work; filled wall-to-wall with brilliantly tense scenes and unforgettable performances. Like much of his output, it’s a wildly entertaining movie that’s also preoccupied with being a movie, and its best moments explore the power of cinema both as a means of entertainment and propaganda.
Above-Average Job, Academy!

6) Argo (2012)
The challengers: Amour, Beasts of the Southern Wild, Django Unchained, Les Misérables, Life of Pi, Lincoln, Silver Linings Playbook, Zero Dark Thirty
The winner: Ben Affleck’s Argo is a fine example of what mainstream prestige cinema can aspire to be. It’s thrilling, entertaining, funny, and generally very intelligent in the way it tells its story. The story of how it won Best Picture is also fairly interesting, since the sudden wave of support seemed to almost be a violent reaction to Affleck getting snubbed for Best Director. When his name was not on the list of nominees, most prognosticators assumed his film was dead in the water, but when the ceremony came around, Argo left on top.
Who should have won: In the couple years since this ceremony, the Best Picture nominee that has stuck with me most is Zero Dark Thirty, Kathryn Bigelow’s deliberate exploration of post-9/11 American intelligence that culminates in the killing of Osama bin Laden in Pakistan. I’ve revisited it several times in the years since, and it leaves a cumulative impact that none of the other nominees can touch.

7) Million Dollar Baby (2004)
The challengers: The Aviator, Finding Neverland, Ray, Sideways
The winner: Million Dollar Baby came out at the tail end of a strong stretch for Clint Eastwood the director, a run that would come to a close with the terrific Letters from Iwo Jima. It’s not a movie at the forefront of anyone’s mind these days, but for the curious, it is more than worth revisiting. Also, despite the whole “winning Best Actress” thing, I feel like Hilary Swank never quite got a fair shake in the years since. She’s great, and we don’t see enough of her onscreen.
Who should have won: Honesty time! Of the other nominees, I have only seen The Aviator, which is quite good. But so is Million Dollar Baby. So I’ll give myself an “incomplete” on this one.

8) The King’s Speech (2010)
The challengers: 127 Hours, Black Swan, The Fighter, Inception, The Kids are All Right, The Social Network, Toy Story 3, True Grit, Winter’s Bone
The winner: Here is a year that perfectly illustrates the Oscar problem. Upon its release in 2010, The Social Network was rightfully hailed as one of the best films of the year, and it wound up at or near the top of nearly every critic list. Then The King’s Speech came out, a genuinely entertaining and more blatantly Oscar-friendly film that had the awards-hungry weight of the Weinstein machine behind it. The Academy bought what the Weinsteins were selling, and it wound up winning big on Oscar night. As a result, even though I liked The King’s Speech a whole lot, I began to resent it. It’s a reminder of how dumb awards are. For one, quality almost never has anything to do with it, and on the other hand, it can create negative feelings toward films that don’t necessarily deserve it. There’s no reason to hate The King’s Speech, but for a couple months, that’s precisely what happened to me.
Who should have won: The Social Network, in case you couldn’t tell.

9) A Beautiful Mind (2001)
The challengers: Gosford Park, In the Bedroom, The Lord of the Rings: The Fellowship of the Ring, Moulin Rouge!
The winner: Among critics, here is a film that gets a lot of mud thrown at it. And, honestly, I haven’t watched it since high school, at which point it was shown in two (2) different classes within a few months of each other. (In hindsight, good work, teachers!) But darn it all, I loved it a lot. I’m sure if I watched it today, my brain might not be too kind to it, so this placement on the list is something of an estimate. It’s lower than 17-year-old me would have placed it, but slightly higher than what 23-year-old me might think. Also, I’m always happy to stand up for Ron Howard, who makes conventional, crowd-pleasing films, but typically does it really well.
Who should have won: Another year with a couple of glaring omissions on my part, since I have not seen Gosford Park or In the Bedroom. (I was 10, leave me alone.) As good as Lord of the Rings is, I’m not sure this first installment is worthy of my retroactive Oscar, and I don’t really remember much of Moulin Rouge! So, I’ll give myself another “incomplete.” This is the kind of expert analysis you come here for, right?

10) Chicago (2002)
The challengers: Gangs of New York, The Hours, The Lord of the Rings: The Two Towers, The Pianist
The winner: It’s been a rough go for Rob Marshall since the massive success of Chicago, and even though it is the first film he ever made, it remains his best by a wide margin. Even so, it comes off as more of an entertaining diversion than a great piece of filmmaking, with a few fantastic numbers stuffed in between stretches that can feel redundant and rushed. All that said, it still might be one of the best musicals to come out of Hollywood since the turn of the century, but that only illuminates how low that bar is these days.
Who should have won: I’m much more comfortable awarding my retroactive Oscar to The Lord of the Rings: The Two Towers, which saw Peter Jackson’s trilogy really kick into high gear.

11) Gladiator (2000)
The challengers: Chocolat, Crouching Tiger Hidden Dragon, Erin Brockovich, Traffic
The winner: Most years, the Academy doesn’t seem terribly keen on historical epics like Ridley Scott’s Gladiator, which turned out to be the first Best Picture winner of the 21st century. Even though it was only 15 years ago, this feels like a different time for the Academy Awards, when audience popularity played a much bigger role in choosing what films to honor. These days, I’m not sure films like Gladiator or 1997’s Titanic would have a prayer. Both are engrossing entertainments on a grand scale, but it seems like a stretch to suggest either were the best to come out of their respective years.
Who should have won: Steven Soderbergh won the Best Director award this year for Traffic, and in my opinion his War on Drugs drama should have walked away with Best Picture as well. By the way, this movie made almost $125 million domestic when it came out in 2000. Would it have a prayer of doing that today? Almost certainly not.

12) Slumdog Millionaire (2008)
The challengers: The Curious Case of Benjamin Button, Frost/Nixon, Milk, The Reader
The winner: Like many of Danny Boyle’s movies, Slumdog Millionaire is a stylish film that is a whole lot of fun to watch. Also, like many Danny Boyle movies, it doesn’t hold up to very much scrutiny. His fairy tale about a young Indian man finding love (and a bunch of money) on Who Wants to Be a Millionaire? certainly resonated with the moviegoing public, but beyond its feel-good elements it all feels just a little too shallow. I’ve seen this movie a couple times, and I always come away wishing I liked it a little more. As mixed as I am about it, there’s no denying its success was encouraging. How often do $15 million films about poor Indian children become massive hits?
Who should have won: Boy, that’s a lousy group of challengers, huh? You’ve got David Fincher’s worst movie alongside a lot of standard Oscar fare that isn’t terrible, but I yawn just looking at the titles. So, uh, nailed it? Great job, Academy.
Bad Academy!

13) The Artist (2011)
The challengers: The Descendants, Extremely Loud and Incredibly Close, The Help, Hugo, Midnight in Paris, Moneyball, The Tree of Life, War Horse
The winner: There may be no figures in the film world more frustrating than the Weinsteins. On the one hand, they gave us filmmakers like Quentin Tarantino. On the other hand, there’s The Artist, just one of many unremarkable films to come out of their factory with an aggressive Oscar campaign at the ready. Every year they seem to get at least one film nominated, and they do everything short of selling a kidney to try and get it the big prize. It works far too often, and the result is winners like this. The Artist is a spring breeze of a movie that somehow convinced voters (and some critics) that it was important, and whenever something like this happens it can be frustrating to watch.
Who should have won: This was never going to win in a million years, but Terrence Malick’s The Tree of Life is easily the most deserving nominee. The idea that someone could watch this film and The Artist and proceed to give the latter an Academy Award is beyond me.

14) Birdman (2014)
The challengers: American Sniper, Boyhood, The Grand Budapest Hotel, The Imitation Game, Selma, The Theory of Everything, Whiplash
The winner: I ranted about this the other day. I’m not sure that any more virtual ink needs to be spilled.
Who should have won: Boyhood, easily. As with 2013, I may have placed another film higher on my personal best-of list (The Grand Budapest Hotel), but if we’re giving out an award celebrating the best filmmaking in 2014, Linklater’s accomplishment feels like the right winner. Alas.

15) Crash (2005)
The challengers: Brokeback Mountain, Capote, Good Night and Good Luck, Munich
The winner: Yeah, take that, you dead horse! Obviously, this is the choice that 99 bloggers out of 100 would have made, but there’s a reason for that. Crash’s win was a perfect storm of silly for the Academy Awards. The entire world was behind Ang Lee’s Brokeback Mountain. Critics loved it. It was a box office hit. It was explicitly about homosexuality, and approached it in a way most other movies up until that point wouldn’t have dared. Ang Lee won Best Director. Full speed ahead, right? Then, Jack Nicholson walks onstage, gives a take to the audience, and blurts out “Crash.” And with that syllable, the outrage began. (If only Twitter was around for that moment. If only.) As with Birdman, the Academy passed over films that actually said something, and instead chose a film that spends most of its time reminding you that it’s saying something. At great volume.
Who should have won: The obvious choice here is Brokeback Mountain, and I’m not here to disagree. But I do want to give a nice shout out to Steven Spielberg’s Munich, his pitch dark and fascinating film about a Mossad agent who finds himself trapped in a cycle of violent revenge in the wake of the terrorist attacks at the 1972 Olympics. Either would have been a good choice.