12 Times Actors Were Cheated Out Of An Oscar

10. 1997 - Matt Damon, Good Will Hunting

Who Actually Won? Jack Nicholson for As Good As It Gets Jack Nicholson is a cranky old geezer with a heart of gold who won an Academy award for playing a cranky old geezer with a heart of gold, thanks to As Good As It Gets. Not exactly a deserving win, seeing as Nicholson has actually been nominated a whopping twelve times, and won the damn thing four times total. That's overkill. Matt Damon, on the other hand, came out of nowhere with Good Will Hunting, having not only excelled in its starring role but co-written it, too. Deservedly, Damon and Ben Affleck won the Original Screenplay award, and it's almost as if it's due to Damon's nascence in the industry that he was locked out of winning two awards. Criminal, considering how good his portrayal of Will Hunting is; rewatch the "It's not your fault" scene sometime, and compare it to the entire 2 hours and 19 minutes of As Good as It Gets. Then tell me which actor deserved the award.
Contributor

Cinephile since 1993, aged 4, when he saw his very first film in the cinema - Jurassic Park - which is also evidence of damn fine parenting. World champion at Six Degrees of Separation. Lender of DVDs to cheap mates. Connoisseur of Marvel Comics and its Cinematic Universe.