The following is judged based on the criteria:
1. THAT'S MY OPINION
2. Overall display of acting talent -- meaning a role that hits the individual actor's strengths
4. The staying power of the performance in popular culture
THIS LIST DOES NOT INCLUDE 2+ TIME WINNERS
Won for "The Hours" (2002) Should have won for "Moulin Rouge!" (2001)
Let's face it, Nicole wasn't taken as seriously as she should have been before her Oscar win. With credits like, Dr. Chase Meridan in "Batman Forever" and fan fave "Practical Magic" it's not hard to see why. However, Nicole's turn as Satine, the headliner of the Moulin Rouge, hit all of Nicole's strong points as a performer. She was funny, she was silly, she made you laugh, she made you ugly cry, she made you a little horny, she made you feel alive. Ultimately, at the 2001 Oscar Ceremony, Halle Berry's historic win (despite the role not aging well on multiple levels, the acting remains iconic) was the correct choice. But it did make Nicole's turn in the following year in "The Hours" seem especially baity with her prosthetic nose. She knew the Academy LOVES a pretty woman in "ugly" make-up. Nicole has yet to take a role as versatile and fun as Satine, and it seems unlikely she'll do so again.
Won for "Fences" (2016) Should have won for "Doubt" (2008)
Oof. Only one other performer has been awarded an Oscar for less than 10 minutes of screen time, Judi Dench. Viola is the most recent performance to join the list of FIVE performances nominated for 8 minutes or less of screen time. This role is the role that put Viola on the map. She plays a complicated, messy, (the now iconic Viola special) yet devoted mother to a boy who may or may not be being abused by a priest. With her limited screen time she absolutely steals the show from the other four nominees from the film. At the ceremony, the Oscar went to Penelope Cruz for "Vicky Christina Barcelona" so you can see how poorly that aged in comparison to Viola's performance.
Won for "Room" (2015) Should have won for "Short Term 12" (2013)
So, the gag is that Brie wasn't even nominated for this performance. She did manage to get nominated, and win, for several Critic Choice awards. If you managed to see "Short Term 12" before you saw "Room" you would know what could have been. The fire and determination and nuance felt a little lacking in comparison to her breakout role. Had she gotten the traction, she would have been up against Cate Blanchett for "Blue Jasmine" and that was a whole lock the entire season so, the academy made good on giving Brie some sort of recognition.
Won for "The Scent of a Woman" (1992) Should have won for "The Godfather: Part II" (1974)
I mean, come on. Even if you know nothing about Al Pacino, you know he played Michael Corleone in the Godfather. This was the film in which Michael fully embraces his role as the new Don of the family and goes full mob boss and wacks a lot of people, including his older brother, Fredo. I haven't seen Scent of a Woman, but I've heard enough jokes that the win is more of a "make-up Oscar" than a legitimate win. Pacino lost to Art Carney for Harry and Tonto, a literal who?
Won for "The Revenant" (2015
Honestly, literally any other movie that Leo was nominated for could have been a better more deserving performance than the "I am vegan and actually got inside a horse" performance. Now, oddly enough, this was another role that wasn't even acknowledged, and it is by far Leo's most consistent performance. Here he still had his youthful looks and leaned into the heart throb yet still serious actor, that we all loved Leo for (until we learned he was gross and the women he dated didn't age with him). "Catch Me if You Can" remains a criminally underrated film for both Leo, Tom and Steven yet spurred a new cultural obsession with Pan Am and the "Carl Hanratty" accent.
Won for "Still Alice" (2014) Should have won for "Boogie Nights" (1997)
Julianne is on the list of any win is the right win, but in terms of pop culture relevance, "Boogie Nights" remains her most iconic role. The movie certainly hasn't aged well, but Moore's Amber Waves is the consistent strong point in the film.
aka not included because I don't want to wank bait
Kate Winslet -- Won for "The Reader" should have won for "Eternal Sunshine of the Spotless Mind"
Sandra Bullock -- Won for "The Blind Side" should have won for "Gravity"
Joaquin Phoenix -- Won for "The Joker" should have won for "Literally Any other Nomination (my personal choice being "Walk the Line")"
Jennifer Lawrence -- not included because it's one of ONTD's talking points that she should have won for "Winter's Bone"
***Final Note: This started out fun, but then got really depressing knowing there was zero diversity of these lists, but I had already done too much HTML to completely waste my time and scrap the idea. :(
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