1993 - 'Unforgiven' vs. 'The Crying Game'
Rule #1 in Oscar voting: Actors who step behind the camera to become directors, writers, or producers will always be rewarded by the acting branch in Hollywood.
After almost 40 years in the biz, this movie marks Clint Eastwood's first ever Oscar win as the director of "Unforgiven," a traditional western—a Hollywood movie invention made at a time when big screen westerns were riding off into the sunset. You could forgive the Academy for rewarding it with a Best Picture win too.
"The Crying Game" would have to dry its tears as the Best Original Screenplay winner. An Irish movie about an Irish Republican Army volunteer who kidnaps a British soldier and then later falls in love with the soldier's girlfriend... who just so happens to be transgendered... is just not very old school Hollywood.
1996 - 'Braveheart' vs. 'The Usual Suspects'
Mel Gibson was a double winner as producer and director of "Braveheart". Here comes magnificent Mel in a kilt, leading an army of angry Scots in the battle for Scottish independence against the British Crown. Never mind if Hollywood has never heard of the Scottish hero, William Wallace. Revolting against the British sounds... downright American! Give it all the awards!
"The Usual Suspects" won the consolation prize of Best Original Screenplay. Sure, "Braveheart" was spectacle. But "The Usual Suspect" still holds up as an ingenious big screen puzzle employing one of the most unreliable narrators of all-time. Who was the mysterious and sinister Keyser Soze? Why, it was the snivelling, pathetic Verbal Kint, this whole time. It's as plain as a crowded bulletin board.
1997 - 'The English Patient' vs. 'Fargo'
Um, did the Academy not listen to Elaine Benes? (See the "Seinfeld" season 8 episode "The English Patient".) "'The English Patient' sucked!" Actually, it didn't. And it's exactly that kind of sprawling, messy love story that the Academy loves. Bonus points for setting it during the Second World War with an international cast. Who knows if Elaine could have swayed voters if she had more time? The movie would win Best Picture only 11 days after the titular "Seinfeld" episode aired.
However, "Fargo", the Best Original Screenplay winner, still sends shivers from the frozen North Dakota twenty years later. Not only does it remain a Coen brothers masterpiece, it introduced us to one of the most-beloved female lead characters of all-time, the pregnant and perceptive cop, Marge Gunderson. And it inspired three more seasons of award-winning television! The problem is that it's a dark comedy. Hollywood never gives the big prize to a comedy—especially not a dark comedy with quirky accents, clueless criminals, and a misused woodchipper.
1998 - 'Titanic' vs. Everybody Else
“Good Will Hunting” was the Original Screenplay winner. So once again, see Rule #1 in Oscar voting. Written by Matt Damon and Ben Affleck, Hollywood was more than happy to reward the two young rising stars… who strangely never wrote another movie together. Sooooo…. one and done, guys?
The Adapted Screenplay winner was “L.A. Confidential”. In any other year, a well-crafted and complex film noir about Hollywood celebrity and police corruption starring an amazing cast would go on to win the Best Picture prize.
But nobody, and I mean nobody, was going to sink “Titanic” in 1998. The highest-grossing movie ever (at that time) also tied “Ben Hur” for the most Academy Awards at 11.
However, for our purposes, it also was the first film since 1965’s “The Sound of Music” to win the Best Picture award— without even scoring a screenplay nomination. But who cares about that clumsy dialogue… did you see that big boat go down?!
2001 - 'Gladiator' vs. 'Traffic'
The Best Adapted Screenplay winner, "Traffic," seemed poised to win the Best Picture prize as well. It seemed epic enough with multiple storylines and an international cost. It was topical too with its movie microscope firmly on the failing war against drugs. And it won Best Director (for former indie darling, Steven Soderbergh). And, as already stated, a Best Director win combined with a Best Screenplay win is a pretty potent combination to win Best Picture.
But the Academy wanted more spectacle. How about a former army general sold into slavery who exacts vengeance on a corrupt Roman emperor? Revolting against the Romans sounds... downright American! Plus Oscar winner, Russell Crowe, was magnetic. And rising star, Joaquin Phoenix, was pathetic. And didn't beloved Ridley Scott, the director of "Alien" and "Blade Runner" and "Thelma & Louise," deserve a little love? (The directors didn't think so; but maybe the Academy would?) After all, "are you not entertained?!"
2003 - 'Chicago' vs. 'The Pianist'
Best Adapted Screenplay winner "The Pianist" certainly held the keys to a huge Best Picture victory. After all, it was a harrowing World War II film based on the memoir of a Holocaust survivor. And just like "Gladiator", it had a Best Actor winner in Adrien Brody.
Was it the Roman Polanski factor? He was a producer on the film—AND a wanted fugitive from the US justice system over a long-standing statuary rape conviction. But that couldn't be it. He still won Best Director that night.
So why did "Chicago" win Best Picture? Lest we forget that it came into the night with the most nominations with thirteen. But really, it's about Rule #2 in Oscar voting: Hollywood loves to celebrate itself. Okay, so it's not a movie about moviemaking. But it's a big, brash musical about scandal and fame—and ain't that Hollywood?
2005 - 'Million Dollar Baby' vs. Everybody Else
"Million Dollar Baby" was money in the bank when it came time to announce the Best Picture. Hollywood loves boxing movies and here was a punchy weeper with a twist (the boxer is a woman!) and a tragic ending (she dies in the end!). Hilary Swank won Best Actress. And Clint Eastwood won another Oscar as the Director. And the Paul Haggis screenplay was at least nominated for a Best Adapted Screenplay.
Well, the wine-swilling road trip movie "Sideways" wasn't going to pop the champagne for Best Picture (the Best Adapted Screenplay winner). Much too small.
And you can forget the Best Original Screenplay winner, "Eternal Sunshine of the Spotless Mind." A romantic sci-fi tragicomedy? Starring that Ace Ventura goofball, Jim Carrey? Much too complicated. Too manic. Too heartbreaking. Too... everything.
Never mind that the cult classic is now considered one of the best movies of the past 25 years. Boxing is simple. You punch each other until the bell sounds. That sounds like a winner.
2012 - 'The Artist' vs. Everybody Else
That's right, "The Artist" won Best Picture. Did you see "The Artist"? And if you did, will you ever see it again?
Well, remember, Rule #2 in Oscar voting? That's why it won. Of course the movie about making movies is going to win. It doesn't matter if it's virtually silent. And starring unknowns. And in black and white. And... French (?).
Speaking of French, "Midnight in Paris" is a talkie that actually takes place in France. It was also the Best Original Screenplay winner and the third writing award (and fourth overall) for controversial filmmaker Woody Allen. It follows Rule #2A in Oscar voting: It's a movie about writing movies.
(Our Best Picture money, eight years later, is still on Adapted Screenplay nominee "Moneyball" by the incredible Steven Zaillian ("Schindler's List") and Aaron Sorkin ("The Social Network"). It did the impossible. It made baseball boardroom statistical analysis exciting. And it had Brad Pitt's abundant charm.)
2018 - 'The Shape of Water' vs. 'Get Out'
That's right, "The Shape of Water" won Best Picture. Well, Hollywood does love a love story. Call it an adult fairy tale... with an aquatic leading man-fish. And it won the Best Directing Oscar. And, as we know, Best Director wins often translate to Best Picture wins. I mean, not in recent years... "The Revenant" didn't beat "Spotlight"... And "La La Land" didn't beat "Moonlight"... And "Roma" didn't beat "Green Book"...
Perhaps the best film of the year should have been the mind-bending horror satire "Get Out", the winner of the Best Original Screenplay? Or was it too innovative? Or too "outside the box" (or fish tank)? No, the problem is that it's a horror movie. Hollywood never gives the big prize to a horror movie.
So the Best Picture winner was given to "The Shape of Water". And I guess some things... like falling in love with a scaly sea creature... just can't be explained.