30 Oscar losers that should have been Oscar winners

Matt Damon losing to Jack Nicholson – Best Actor (1998)

The Winner

Jack Nicholson, playing Melvin in As Good As It Gets. He’s rude and offensive and takes advantage of the people around him. He’s also emotionally manipulative. But we’re supposed to care about his personal growth instead of praying that these poor supporting characters get away from him.

The Loser

Matt Damon in the role he and Affleck won an Oscar for writing. Will Hunting, a janitor in Boston, turns out to be a mathematical genius. But the real question is whether he can accept his own talent when it takes him farther away from everything he knows.

Why It Was Wrong

Again – I don’t get As Good As It Gets. Again – Jack Nicholson is an undeniable master of his craft. But I find that the Oscar almost always gets tipped to the older, more established entity in the business. Case in point, the previous slide. Kate Winslet was a green teenager who carried off one of the most difficult performances of the year. But she was snubbed in favor of Helen Hunt, who had been acting since she was a child and starring in Mad About You for five years. I think we have a similar situation here.

Damon had been in just a couple of mainstream movies before he wrote his own starring role in Good Will Hunting. But it will be no surprise to hear that Nicholson was already a Hollywood mainstay. He already had two Oscars at the time. Huh…it’s as if the Academy voters would rather go with something they’ve seen before than even consider the greatness of something new. [/heavysnark]

Again, I’m not here to say that Nicholson’s performance wasn’t good. But the emotional intensity of Damon’s work, and the subtlety and nuance with which he carried it off, deserved better. I know he won another one that night for writing, but a double-win would have totally been warranted.