Nicolas Cage's Oscar often feels like a fluke when you look at his career as a whole. He went all-in for Leaving Las Vegas, but that kind of extreme, high-volume acting isn't for everyone. The win now seems like the Academy rewarding a single moment of dramatic frenzy rather than recognizing a consistently great actor. | © MGM
Art Carney's Oscar is really a career achievement award given for a minor, sentimental role. He's fine in Harry and Tonto, but the film itself is so slight that his performance never truly stands out. It's especially hard to justify when you remember he beat Al Pacino and Jack Nicholson at the absolute peak of their powers. | © 20th Century Studios
Cher’s Oscar often gets brushed off as the Academy being charmed by a superstar stepping outside her lane. Sure, she’s magnetic in Moonstruck, but the win has always carried a whiff of novelty, like voters were rewarding her for being a convincing actress rather than the best actress. In a year heavy with dramatic performances, giving the trophy to a romantic comedy felt like choosing a fun diversion over substantial acting. | © MGM
That Oscar for Jerry Maguire is the kind you get for having one incredibly loud, memorable moment that defines a film. Gooding Jr. is all energetic charm in the role, but there's not much going on beneath the surface. Given how his career panned out afterwards, the win just seems like the Academy fell for a flashy bit of crowd-pleasing rather than honoring truly great acting. | © Sony Pictures Releasing
It's almost frustrating that Gary Oldman's Oscar came for Darkest Hour. After a career of transformative roles, his win was for a safe impersonation of Winston Churchill. In a year with bold work from actors like Timothée Chalamet and Daniel Kaluuya, rewarding such a by-the-numbers bit of Oscar bait felt like the Academy finally giving him a trophy for all the wrong reasons. | © Focus Features
Halle Berry’s Oscar is historic, but that very fact complicates how people see the win. Her performance is intense, but the role itself is so narrowly written that it doesn't offer much beyond its heavy moments. It often feels like the Academy was honoring a symbolic breakthrough, not necessarily the most substantial acting that year. | © Lionsgate Films
Tom Hanks' back-to-back Oscar for Forrest Gump now feels like overkill. He's undeniably likable in the part, but the mannered voice makes it feel like a one-note character piece next to the complex work of his competitors. Watching it today, you can't help but think Morgan Freeman in Shawshank or John Travolta in Pulp Fiction were just robbed. | © Paramount Pictures
Few wins are as synonymous with Oscar politics as Gwyneth Paltrow's for Shakespeare in Love. She's perfectly charming in the role, but the performance feels slight compared to the career-defining work the Best Actress award usually honors. The victory has aged into a case study in how a well-timed narrative and a studio's aggressive push can overshadow actual talent, forever overshadowed by the fact that it beat Cate Blanchett in Elizabeth. | © Universal Studios
When people talk about Oscar misfires, Rami Malek winning for Bohemian Rhapsody is often the first that comes to mind. The performance is a distracting imitation, all exaggerated, that never connects with Freddie Mercury. It’s the rare case where voters seemed to reward the idea of a challenging biopic role over what was actually on screen, making Bradley Cooper’s loss for A Star is Born feel especially baffling. | © 20th Century Studios
The Academy has a well-known soft spot for biopics, and Redmayne’s Oscar is proof of that. He delivered an all-in physical transformation for The Theory of Everything, yet the performance can feel like a series of calculated Oscar clips rather than a lived-in character. When you remember he beat Michael Keaton's career-reviving turn in Birdman, the win starts to look more like a reward for playing the Oscar game correctly. | © Focus Features
The Oscar for The Blind Side is often cited as a prime example of the Academy rewarding a likeable star in a crowd-pleasing story. Bullock’s performance is charming, but it leans so heavily on her natural charisma that it never really pushes into more challenging territory. Given how the film’s simplistic take on its subject has aged, the win now feels more like a celebration of Hollywood sentiment. | © Warner Bros. Pictures
Roberto Benigni is the ultimate example of Oscar voters rewarding a film's overwhelming heart rather than a nuanced performance. His broad style in Life Is Beautiful was a huge gamble, it either moves you deeply or feels completely over-the-top. That unforgettable awards night sprint just cemented the idea that the Academy fell for emotion of it all, making it a perennially debated pick. | © Miramax Films
Kim Basinger's win for L.A. Confidential often gets tagged as the safe choice in a stacked cast. She was perfectly good, but in a film brimming with more complex characters, her quieter role never truly dominated the conversation. Looking back, it feels like the Academy picked a moment of solid work from a beloved film, rather than awarding a performance that would resonate for years. | © Warner Bros. Pictures
Jared Leto winning for Dallas Buyers Club is what happens when voters confuse a drastic physical change with a deep performance. He leaned hard into tics and intensity, but it often played more like a showy stunt than real character work. After a string of divisive roles since, that Oscar now looks less like a career milestone and more like a prize for commitment to a single, flashy bit. | © Focus Features
Some Oscar wins age like fine wine, others like milk left in the sun. For every acclaimed performance that earns a trophy, there’s a winner that leaves audiences scratching their heads. These are the actors whose Oscar victories remain the hardest to defend.
