Five actors who desperately crave the Oscar they’ll never win
We can all sit here and pretend they’re not, but let’s be honest, the Oscars are the pinnacle of the film world.
There are plenty of other honours that probably mean more in terms of actually good films or actually good performances. A film winning the Palme d’Or at Cannes Film Festival, for example, feels more likely to be representative of actual good art than a ‘Best Picture’ nomination, but when we’re talking about the big leagues and about the top dogs of Hollywood, nothing speaks to status or ranking quite like one of the gold guys.
However, they’re also a strange and fickle thing. Throughout the awards’ history, there have been plenty of controversies about the way the voting body actually runs, and plenty of almost criminal underevaluations of films and performances, so rightfully, plenty of people are cynical about it all. There are plenty of actors who really, truly deserve to win who never have, but also, when it comes to looking forwards to the new generation of stars, it feels easy to spot the names who seem destined to one day win.
Yet no one really admits they want to. In 2026, Timothée Chalamet was a rare example of a star being outright about wanting to take home a trophy. Though he didn’t in the end, it feels inevitable that one day he will be, given how many times he’s already been nominated for his young age. However, the flip side to that is the tragic names where it feels pretty clear that no matter how hungry they are, it’s simply not in the cards for them to take home a victory.
Five actors who will never win an Oscar:
Ethan Hawke
Ethan Hawke deserves an Oscar. Decades into his career, he remains one of the most booked and busiest men in Hollywood and each and every time, he delivers greatness. The issue is that overwhelmingly, Hawke deserved an Oscar: past tense.
Part of the Oscars issue is that often, they seem to overlook someone’s opus. It will forever feel strange that Leonardo DiCaprio eventually won for The Revenant and not any of his far better projects when he was younger. Part of the problem with awards seasons happening year on year is that the greatness of a performance sometimes takes a while. Sometimes a person’s absolute best work can pass by unappreciated by these bodies, and then after that, the actor feels doomed to never really be able to catch up.
I’d argue that happened to Ethan Hawke several times over. If he was going to win an Oscar, he should have won it for Dead Poets Society, or his performances across the Before trilogy, and the nomination in 2026 for his Richard Linklater return felt like an acknowledgement of that.
But still, Hawke was a rare name that was willing to admit that he wanted it. “Embarrassingly enough, it means a lot,” he told the LA Times, “I’ve dedicated my life to this profession, and our culture places a high value on that. And it means a lot to me”. Yet sadly, I don’t see it on the cards for him, except maybe a token lifetime achievement retrospective award down the line.
Steve Carrell
This one makes me sad.
Like Hawke, Carrell, I’d argue, deserves an Oscar. By now, it is basically impossible to imagine modern comedy without Carrell, as his list of titles, from Bruce Almighty to The 40-Year-Old Virgin, defines that classic 2000s vibe of laughs.
But beyond that, Carrel has also delivered some serious and staggering performances. His role in Little Miss Sunshine was proof that he could, but then it was 2014’s Foxcatcher and 2018’s Beautiful Boy that went even beyond expectations.
In an interview on SBIFF, recalling the morning he got the nomination for Foxcatcher as he ran up and down the stairs with excitement, you can see the glimmer in his face of how much he wanted it. But also, there’s the sad acceptance that it always seems completely impossible for funny men to be recognised by the serious body. The fact that his devastating performance in Beautiful Boy wasn’t even considered feels like proof that Carrell is written off as nothing but a laugh.
It’s a feat that no one but Robin Williams has ever really managed to pull off, and so no matter how worthy Carrell is, it doesn’t feel like he’ll ever make the transition from jokester to Oscar winner.
Cynthia Erivo and Ariana Grande
We’re treating these two as a package deal because their desperation was one.
During the first Wicked press tour, it felt like you couldn’t breathe without Cynthia Erivo and Ariana Grande being there, crying, holding hands, gushing about how much Wicked meant, how hard each other worked, how much of a dream it all was and so on. They were everywhere, in every outlet, and all of it seemed to be culminating towards the Oscars.
Wicked did get nominated for a lot, including a ‘Best Actress’ and ‘Best Supporting Actress’ nomination for both of the stars. However, was anyone surprised when both lost? No.
Obviously, both are talented, but they both feel talented in different realms rather than the true movie focus of the Oscars. Grande was impressive as Glinda, but only because her hunger and love for the role shone through. Erivo was impressive because she is clearly made to be a musical theatre star, and that’s why I think she’ll never get the gold man.
Erivo is only an Oscar away from the coveted EGOT, but her performance as Elphaba and their insufferable press tour reeked of that desire. The fact that neither actor nor the film itself earned any nominations for the sequel proved that to me, as the follow-up film, which should have been its emotional climax, their desires flopped.
Ashley Benson
“My goal is to win an Oscar, and I’m going to take the steps to get there,” said poor, sweet, delusional Ashley Benson.
Back in 2013, when she shared her goal with Teen Vogue, perhaps it felt realistic. At the time, she was the ultimate queen of the teen scene thanks to her role in Pretty Little Liars, and then her bursting into the world of features in the cult favourite Spring Breakers, starring alongside a cast of other child stars and ex-Disney kids in a film that felt purpose-built to pop the innocent perceptions and move them into grown-up roles.
But over a decade on, Benson’s career clearly hasn’t gone the way she hoped. There are projects on her filmography that didn’t even make an impression big enough for someone to make a Wikipedia page for them, so unless something changes and she’s miraculously cast in some incredible role that completely reintroduces her, it doesn’t feel likely.
Bradley Cooper
Nothing smacks of desperately wanting to win an Oscar more than passionately talking about how much you don’t want to win an Oscar.
In 2013, he claimed, “I don’t want to win an Oscar”, which came conveniently after he’d missed out for the ‘Best Supporting Actor’ trophy for Silver Lining Playbook, and he doubled down, adding, “It would change nothing. Nothing. The things in my life that aren’t fulfilled would not be fulfilled.”
In 2020, he went in again, this time after missing out on three awards for A Star Is Born, now saying the trophy would be “utterly meaningless”. But the question is, if Cooper really, really doesn’t want an Oscar, why does he keep making such intensely Oscar–baity films, like 2024’s blatant Maestro?
The problem now is that it’s exactly Cooper’s pathetic desperation, masked by repeatedly bad-mouthing the event, which will keep him from getting one. Sure, there have been moments in his career where maybe he should have bagged it, but isn’t it much more fun watching him constantly throw his toys out of the pram?
