People who won an Oscar for the "wrong" film

[DiBiase is Good]

So, Leonardo DiCaprio finally has an Oscar. Although some people have suggested that he might not have deserved it this year and one of his other nominated performances should have been the one that he won.
What are your choices for people (be it Actors, Actresses, Directors, Writers) who have won an Oscar but should have won it for a previous or later nomination? It doesn't have to in the same category, so you can say instead of winning Best Actor tonight, DiCaprio should have won Supporting Actor for What's Eating Gilbert Grape.

I'll say Martin Scorsese winning for The Departed. He should have won for Goodfellas or Raging Bull.
Steven Spielberg winning for Saving Private Ryan. He should have won for E.T. (His other win for Schindler's List was deserving)
Jeff Bridges should have won for True Grit, not Crazy Heart.
Judi Dench should have won for Mrs. Brown instead of Shakespeare in Love.
Al Pacino should have won for just about any other nomination instead of Scent of a Woman. (If I had to pick a couple it would be The Godfather Part II or Dog Day Afternoon.

[Citizen Snips Has Left]

Denzel Washington for Training Day instead of Malcolm X

Charlie Chaplin for either Best Actor, Best Screenplay or Best Picture for The Great Dictator instead of Best Score for Limelight

[bibboid]

Paul Newman should have won the Oscar for The Hustler. The academy didn't give him a non-honorary Oscar until The Color of Money.

[Milkman Norm]

Russell Crowe should have won for The Insider instead of Gladiator.

[Bob Schlapowitz]

Al Pacino for Scent of a Woman instead of Godfather (and Part II).

Whoopi Goldberg for Ghost instead of The Color Purple.

[Mozenrath]

I assume we're just talking their best work in a vacuum, not having to debate what it was up against?

[pegasuswarrior]

Feb 29, 2016 3:29:10 GMT -5 Milkman Norm said:

Russell Crowe should have won for The Insider instead of Gladiator.

Boom! That's my go-to selection. And that includes what it was up against at the time.

Another poster just made the most valid post that nails a pet peeve of mine. People say shoulda shoulda shoulda all the time, but they don't look at the work they were up against in those years a lot of times. Not saying that the Oscars get it right every year. I'm just saying hindsight about this kind of topic works a lot of times only with blinders on.

[DiBiase is Good]

Feb 29, 2016 6:53:41 GMT -5 Mozenrath said:

I assume we're just talking their best work in a vacuum, not having to debate what it was up against?

As it's hypothetical, I would say it's up to you if you want to factor in actual winners. Like, I can agree that Russell Crowe should have won for The Insider instead of Gladiator without then having to debate if his performance in The Insider was better than the actual winner that year (Kevin Spacey in American Beauty).
I could also say something like Sean Penn should have won for Dead Man Walking instead of Mystic River. This then means that Bill Murray could have won for Lost in Translation that year instead.

[revolver86]

Leo should have won for Wolf of Wall St. I thought that was Leo at his best.

[BRV]

I feel like the only person on earth who thought Leonardo DiCaprio's win for "The Revenant" was the first time he was nominated and actually deserved to win.

His three other best actor nominations were for "The Aviator", "Blood Diamond", and "The Wolf of Wall Street". I thought he was perfectly fine in the first two and I've been on record numerous times in saying how I thought "The Wolf of Wall Street" sucked a big bag of asses, so I felt like "The Revenant" was the first time he won the award he truly deserved.

[ibdude]

Denzel Washington should've won Best Actor for Malcolm X. He had a good role, but that shouldn't have been the first time he won the Oscar.

[Ben Wyatt]

Feb 29, 2016 10:44:33 GMT -5 BRV said:

I feel like the only person on earth who thought Leonardo DiCaprio's win for "The Revenant" was the first time he was nominated and actually deserved to win.

His three other best actor nominations were for "The Aviator", "Blood Diamond", and "The Wolf of Wall Street". I thought he was perfectly fine in the first two and I've been on record numerous times in saying how I thought "The Wolf of Wall Street" sucked a big bag of asses, so I felt like "The Revenant" was the first time he won the award he truly deserved.

I'm sure I'm in the minority, but I thought he deserved consideration for "Catch Me if You Can"

[Juice]

Leo last night for sure. The Revenant was great and all, but he was outshined by the competition. That was a "we f***ed up, now here's your statue" if I ever saw one.

[Crimson]

Martin Scorsese getting Best Director for The Departed. He should have won for Raging Bull or GoodFellas.

[Deleted]

Dame Judy Dench.

Nominated in 1997 for Mrs. Brown, heavily favored to win (the notability of the movie led to basically her US film career), lost to Helen Hunt (As Good as It Gets) -- nominated the next year for what seemed like an extended cameo in Shakespeare in Love (2 scenes, I think), won.

[The Tank]

*opens mouth to rant about Sean Penn, then reads the OP completely*

Ah. Something we feel they should've won for instead of just where someone who shouldn't have won won it.

I'll, uh...I'll go bitch about Milk somewhere else, then.

*walks out muttering about Mickey Rourke getting robbed*

[Psy]

Leonardo DiCaprio should have won Best Actor for Critters 3. Well, not really... I just wanted to remind people that he was in it.