Supposedly Fun

At this point, we are halfway through this decade of Best Actress winners. Sure, there’s more to come, but there’s nothing wrong with getting ready, right? I’ll keep adding the winners of the Academy Award for Best Actress as they happen and we’ll see what this ranking looks like by the end of the decade. If you’d rather browse completed lists in the meantime, feel free to do so.

First, some notes on how I do this. I will comment on whether or not a win was deserved but worthiness alone cannot impact the ranking. Also, please note that for me, these are fluid lists. As I revisit and rethink the winners, I may decide to move rankings around. My list, my rules.

6. Jessica Chastain, The Eyes of Tammy Faye (2021)

It would be tempting to lob a complaint at Jessica Chastain that is similar to the one I had against Will Smith, the Best Actor winner for this same year. That is to say, it would be tempting to say that while Chastain does a great impression of televangelist Tammy Faye Baker, she doesn’t dive deep into the interior. The difference here is that so much of Tammy Faye really was about the surface–and Jessica Chastain seems to understand that quite well. And there are moments when an almost desperate yearning seems to radiate from her very being, which feels appropriate for the role.

Just like the 2020 Actress race, this was another barnburner. It felt like any of the five nominated actresses had a shot at a win (and at different points of the campaign process were favored to take the whole thing). While Penelope Cruz seemed to be surging toward the finish line, Chastain ultimately emerged with the trophy in hand.

Should have won in 2021: I know she had recently won this category for The Favourite, but Olivia Colman is just. So. Good. in The Lost Daughter.

5. Emma Stone, Poor Things (2023)

I really did not like Poor Things, and I’ve struggled with whether my opinion of the movie has colored my opinion of Emma Stone’s performance in it. I also admit to some residual bitterness about Emma Stone’s Best Actress victory for La La Land. But here’s where I’ve come out on this: Emma Stone really did deserve to win Best Actress for Poor Things. If this had been her first win, I would feel a lot less bitter. But she did deserve this Oscar. Nevertheless, I respond to the higher-ranking performances more.

Should have won in 2023: You could argue that Lily Gladstone should have competed in Best Supporting Actress for Killers of the Flower Moon, but I accept her reasoning that her character is the heart of that movie (even though she is sidelined for a large portion of the film). I originally would have given Gladstone my vote, but I’ve come to peace with the way things played out.

4. Mikey Madison, Anora (2024)

Mikey Madison is in every scene of Anora, so her performance is absolutely essential to the film’s success (it also won Best Picture, Best Director, Best Editing, and Best Original Screenplay). You could make a case that another actress would have done as well, but I was spellbound by Mikey Madison. She perfectly fits Sean Baker’s intention to allow the viewer to graft their own moral to this story of a sex worker who impulsively marries a wealthy (and obnoxious) Russian, only to have his parents disapprove so strongly that they send enforcers to quickly annul the marriage. She doesn’t give anything away, but as the story plays out she perfectly conveys that Anora grabbed onto this marriage out of desperation. She thought this was her happily ever after, and it’s all crashing down on her. All the confidence and swagger she deploys is for show, so no one can see the real, vulnerable Anora lurking underneath the facade of Ani.

It’s a staggering, revelatory performance.

Should have won in 2024: Best Actress was believed to be in the bag for Demi Moore’s raw performance in The Substance. That made Madison’s win one of the most jaw-dropping moments of the night. And while I feel bad for Demi Moore, who was great in The Substance and whose comeback narrative felt earned, I would have voted for Madison over her. Although, to be fair, I have not seen I’m Still Here at the time I am writing this, and I’ve heard from Oscar pundits I tend to listen to that in a just society, this award would have belonged to Fernanda Torres. Until I see that movie and can make a final determination, I’m very comfortable with Madison’s win.

3. Michelle Yeoh, Everything Everywhere All At Once (2022)

Without Michelle Yeoh’s aching, overburdened, and quietly angry mother at the core of Everything Everywhere All At Once, it would be difficult to get the audience to go along for the truly wild ride that the movie is. But everyone in the cast is doing their part to sell the film, not just Yeoh. That’s why this became the first movie to win six (SIX!) of the biggest Oscar categories: Best Picture, Best Supporting Actor, Best Supporting Actress, Best Screenplay, Best Director, and Best Actress for Michelle Yeoh. Yes, Yeoh does a lot of the heavy lifting, but at its heart, Everything is a team effort.

Not that that takes anything away from Michelle Yeoh, who finally earned Academy recognition after decades of solid work that was overlooked–largely because it didn’t fit the type of role the Academy likes to reward. Yeoh is even one of the best Bond Girls ever, for crying out loud.

Everything is the perfect movie to showcase Michelle Yeoh’s range of talents. She gets to be a dramatic actress weighed down by routine, stress, and expectation. She gets to be an action superstar, performing incredible stunts throughout the film. She gets to be a romantic lead as she reconnects with her husband. Most importantly: she gets to be funny without sacrificing any of the other things she’s balancing.

Should have won in 2022: Based on my signature question, you could argue that Cate Blanchett is a better choice because Tár is specifically built around Blanchett’s towering performance (the script was even written for her). And without much of a supporting cast to back her up, Blanchett is more essential to Tár. The movie crumbles without her. And yet, I’m still on team Yeoh.

2. Frances McDormand, Nomadland (2020)

If you want to talk about a performance that is absolutely essential to whether or not a movie works, this has to be it. With a limited supporting cast (mostly comprised of actual nomads who are not actors), McDormand’s only real costar is director Chloe Zhao–the only person who works with McDormand to set the tone of Nomadland. McDormand even helped shape the movie, not just as a producer but as a human who made the nomad community comfortable on a film set–not just as performers but as people willing to share their lives with a film crew. If you take Frances McDormand away from Nomadland, it simply does not work.

Yet it’s surprising to remember that this win nearly didn’t happen.

Best Actress has become one of the best categories in any given Oscar year. At no time was this more true than in 2020, when there was no frontrunner and any one of the nominees could have easily emerged as the winner. Only one nominee, Vanessa Kirby, got through award season without a major televised award. It was a category that was nearly impossible to predict. McDormand, who had won her second Oscar three years earlier, may have gotten an edge here because she starred in the clear Best Picture winner.

Interestingly, McDormand’s second and third Oscars were for performances dealing with grief, yet they couldn’t be more different. Three Billboards, which I called a Garbage Movie, is about grief that is expressed as rage. Nomadland is much quieter. In it, McDormand settles into life in a van-dwelling community of nomads after losing her husband, her job, and her home in quick succession in the economic collapse of 2008. As she weaves from location to location and job to job, McDormand imbues the film with a natural curiosity and kindness. It’s a master class in subtlety–the kind of performance that doesn’t always catch the Academy’s attention but deserves all the recognition it gets.

Should have won in 2020: McDormand was and is my choice. Nomadland wouldn’t be anywhere near the movie it is without her delicate, empathetic work.

1. Jessie Buckley, Hamnet (2025)

The moment you see Hamnet, you know that Jessie Buckley’s performance is an all-time great. She’s radiant and powerful as an independent-minded woman in a time when that was frowned upon, as the wife and love of William Shakespeare, as a fiercely loving and caring mother, and as a woman experiencing the profound grief that comes with the loss of a child. She makes Agnes feel like a real, vibrant person. There’s tremendous depth and nuance supporting the “showier” parts of the role, making this the perfect blend for Oscar bait. Jessie Buckley is incredible in Hamnet, and I’m so glad that she won an Oscar for her work.

Should have won in 2025: In case you couldn’t tell: Jessie Buckley. Full stop.

Other Rankings for the 2020s

Best Picture

Best Actor  •  Best Actress

Best Supporting Actor  • Best Supporting Actress

Best Original Song