The Oscars are the definitive award for motion pictures, the highest achievement in film. But, the Academy has been known to make some bone-headed decisions in the past giving awards to inferior films or performances while passing up clearly superior fare. These are Oscar's biggest misses.
Two notes on the criteria: first, a "miss" is a blatantly bad call, not a matter of personal preference. For example, looking back, it seems crime that Jack Nicholson didn't win Best Actor for Five Easy Pieces until you remember that was the year George C. Scott won for Patton. Second, it's too much to take all of a year's films into account so I've just looked at the nominees, i.e., the choice that the whole voting body would have had.
In the Heat of the Night beating the Graduate
While perhaps the most obvious miss in this category is Crash beating Brokeback Mountain a few years ago, a result that still has people shaking their heads, the Graduate losing to In the Heat of the Night in 1967 is just as, if not more, egregious. There's a similar problem with the Academy's thinking with both examples: both In the Heat of the Night and Crash are meditations on racism, an easier issue for the Academy to parse than what is being dealt with in Brokeback and the Graduate. In the case of the Graduate, the Academy also ignored a movie that ushered in the culture that would continue to be explored in the movies of the 1970s. It's a particularly stodgy choice.
Robert Redford (Ordinary People) beating Martin Scorsese (Raging Bull)
It's hard to imagine what the Academy was thinking here. Raging Bull is such a powerful film that is told with incredible force and power, the only possible explanation is that the Academy was too scared of it and thus chose the safer work of Redford in the safer film.
Julia Roberts (Erin Brokovich) beating Ellen Burstyn (Requiem for a Dream)
There's no doubt that Erin Brokovich is the kind of film that the Academy loves with its big name star and director, its true story credentials and the general feeling of righteousness that it engenders but Roberts' performance really doesn't compare to what Burstyn does in Requiem. Requiem is a difficult movie to say the least and Burstyn's turn is the heartbreaking center of it.
Another Best Actress
Judy Holliday (Born Yesterday) beating Bette Davis (All About Eve)
Born Yesterday is fine and Judy Holliday is fine in it. However, Bette Davis is masterful in All About Eve, it is an iconic performance that continues to captivate and amaze. It is more than a little astounding that the Academy didn't recognize it at the time.
(*I previously identified this as Best Supporting Actress because I misremembered it. Sorry.)
Humphrey Bogart (the African Queen) beating Marlon Brando (A Streetcar Named Desire)
Bogart's African Queen win is a typical Academy make up call. After they passed his Casablanca performance over for Paul Lukas' Watch on the Rhine performance in 1941, they chose Bogart here out of sentiment and ignored Brando when he was the new guy. Brando would lose two more times before winning for his performance in On the Waterfront in 1954.
Best Supporting Actress
Ethel Barrymore (None but the Lonely Heart) beating Angela Lansbury (Gaslight)
For some reason, the Academy isn't wild about films that would later become noir classics and Angela Lansbury being passed over in Gaslight is just another in a long line of examples of this bias. Also at play here is the sentiment value and giving an award to someone who is part of Hollywood royalty. There's no doubt that Ethel Barrymore is good, but Lansbury in Gaslight is better.
Best Supporting Actor
Tommy Lee Jones (the Fugitive) beating Ralph Fiennes (Schindler's List)
The Academy really loved the Fugitive for some reason, besides Tommy Lee Jones' nomination, it received six Oscar nominations including Best Picture. And while it makes sense that the Academy wasn't going to let Schindler's List sweep the night, Fiennes' performance is far better and much more nuanced than the stock performance Jones delivers. Another contender for biggest miss in this category is Tom Cruise in Magnolia losing to Michael Caine in the Cider House Rules, in what was clearly a sentiment-based vote for a bland performance in a totally forgettable film.
Best Original Screenplay
Pillow Talk beating 400 Blows, North By Northwest and Wild Strawberries
In recent years, the Original Screenplay Oscar has gone to very deserving and generally smaller films that the Academy didn't recognize in larger categories; films like Fargo, Almost Famous and Little Miss Sunshine come to mind immediately. But that wasn't the case in 1959 when the Academy gave the award to the most standard of romantic comedies, Pillow Talk, and passed over three - three! - films that would become all time classics. There's no point in singing the praises of 400 Blows, North By Northwest and Wild Strawberries, it's all been said before. The Academy's thinking here is as mysterious as it is misguided.
Best Adapted Screenplay
Here Comes Mr. Jordan beating the Maltese Falcon
This one is completely ridiculous: the story of a man returned to Earth from Heaven for a second chance somehow beating out the quintessential private eye film based on a classic Dashiell Hammett novel is really and truly insane. The Maltese Falcon is another film that we recognize as a classic and a paragon of the form but the Academy didn't think it was a well written enough for an Oscar, and that's totally nuts. Another example of a noir masterpiece that the Academy passed over came three years later in 1944 when Double Indemnity was beaten out by the clearly inferior Going My Way.
Best Original Song
"You Must Love Me" (Evita) beating "That Thing You Do" (That Thing You Do)
It's really hard to imagine that, at one point, the awards circuit was dominated by the piece of dreck that is Evita but its Oscar win for Best Original Song is the most offensive of its accolades. Not only is "That Thing You Do" the far better song but you hear it around one hundred times during the course of the movie and it never gets annoying because it is a pretty perfect piece of pop music. Not only that, but the film lives and dies by it: if it wasn't a fun, eternally listenable song, the whole movie would collapse in on itself, and "That Thing You Do" sustains the whole time. There are few songs that mean as much to the movie they're in than "That Thing You Do."