The Oscars mean everything and nothing all at once. At face value, the Oscars are merely trophies handed out by Hollywood to Hollywood. But in practice, actually winning one of these statues can change the course of a performer’s career. It can open doors to exciting new projects, allow an actor to be picky or choosy about what they do next, or, as it's not entirely uncommon, it can turn out not to change a darn thing.
The Best Actress category is perhaps the most interesting of the entire Academy Awards. Often the most competitive, and often the one that attracts the most ardent fascination from hardcore Oscar fans, Best Actress is the most complex of the four main acting categories, a place where ingenues and overdue veterans come to duke it out, with only one winner. A lot of genuinely incredible performances make up this list, including a few that are among the best in the 21st century. Some hold up better than others, but all reflect some of the best actresses working today. Without further ado, here’s every Best Actress Oscar winner of the 21st century, ranked.
26 Sandra Bullock – 'The Blind Side' (2009)
Who Should Have Won: Gabourey Sidibe in 'Precious'
This Oscar win has aged the worst of any on this list. Sandra Bullock is a terrific actress, but her win as a rich white woman who fosters a poor Black child over Gabourey Sidibe’s gut-wrenching turn in Precious – a story by and about members of the Black community – still leaves a bit of a rotten taste in my mouth (and that's even before you get into the lawsuits and questionable conservatorship that came in the years to come with the family at the center of this story.). But it’s not only the juxtaposition that makes this win kind of cringeworthy, but it’s also not even that great of a performance – I wouldn’t even put it in Bullock’s top 5. Again, this is nothing personal against Bullock, who is terrifically talented, but, woof, the Academy sure did get this one wrong.
25 Kate Winslet – 'The Reader' (2008)
Who Should Have Won: Meryl Streep in 'Doubt'
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Here is proof positive that Harvey Weinstein’s influence on the Academy was extremely powerful. Up until the awards season that year, The Reader was a bit of an “also-ran,” and Kate Winslet was considered a stronger candidate for her co-starring role in Sam Mendes’ domestic drama Revolutionary Road. But lo and behold, Weinstein managed not only to get Winslet a Best Actress nomination, but the film itself edged out The Dark Knight for a Best Picture nomination as well. And looking back, Oscar host Hugh Jackman’s opening number about not having seen The Reader kind of says it all. The actress is perfectly fine as a former Nazi concentration camp guard, but The Reader is nowhere near one of Winslet's best performances.
24 Nicole Kidman – 'The Hours' (2002)
Who Should Have Won: Renée Zellweger in 'Chicago'
As Matt Damon says in Ocean’s Thirteen, the nose plays. Nicole Kidman underwent a pretty shocking physical transformation by wearing a false nose to play celebrated author Virginia Woolf in the triptych drama The Hours, and while it’s a very fine nose, her performance is quite solid as well. The film’s structure means Kidman only gets 1/3 the screentime of her co-stars, and I might argue Julianne Moore gives the more memorable performance in the film, but Kidman is good and has a couple of really emotional scenes that played well to the Academy – especially at this particular time, when prestige dramas ruled the roost.
23 Meryl Streep – 'The Iron Lady' (2011)
Who Should Have Won: Viola Davis in 'The Help'
The Iron Lady is a very bad movie, but Meryl Streep – quite possibly the best actor of all time — is pretty good in it. It's a trend you’ll see occurring more than a few times on this list, and it’s not exclusive to the Best Actress category. A great performance is a great performance regardless of the film surrounding it, and Streep nails the bombastic nature of Margaret Thatcher while also showing the controversial Prime Minister’s more emotional side here and there. Still, even though The Help is far from a great film, Viola Davis’ performance there felt a bit more complicated.
22 Jessica Chastain - 'The Eyes of Tammy Faye' (2021)
Who Should Have Won: Kristen Stewart in 'Spencer'
By the time Jessica Chastain won an Oscar for The Eyes of Tammy Faye, she probably should've already had one. Chastain has been doing incredible work throughout the 21st century in films like The Tree of Life, Zero Dark Thirty, and Take Shelter, and the actress was long overdue for a win by 2021. While Chastain's performance as Tammy Faye Bakker might not be her best role, it's a testament to Chastain's talents that she makes this performance not feel like a caricature.
21 Reese Witherspoon – 'Walk the Line' (2005)
Who Should Have Won: Reese Witherspoon in 'Walk the Line'
The casting of Reese Witherspoon as June Carter-Cash was pitch-perfect, and this performance still holds up as a fun, effective turn in the kind of music biopic that became so prevalent it turned into parody (literally, watch Walk Hard). She may not have a scene as intense as the one in which Joaquin Phoenix breaks a sink, but what Witherspoon brings to the role is a sense of confidence and empathy that allows the audience to understand why June stuck with Johnny through thick and thin.
20 Frances McDormand – 'Three Billboards Outside Ebbing, Missouri' (2017)
Who Should Have Won: Sally Hawkins in 'The Shape of Water'
Again, we come to one of the best actresses of all time winning for, well, a perfectly fine movie and performance. Frances McDormand is certainly powerful in Martin McDonagh’s divisive Three Billboards Outside Ebbing, Missouri, and she rattles off McDonagh’s profanity-laden dialogue as if she’s singing a song. The movie itself has kind of faded from memory rather quickly – it very much felt like a story about a very particular, very angry moment in time – but McDormand’s performance is still pretty excellent. And yet, Sally Hawkins’ wordless turn in the Best Picture winner The Shape of Water probably should’ve taken this one.
19 Jennifer Lawrence – 'Silver Linings Playbook' (2012)
Who Should Have Won: Jessica Chastain in 'Zero Dark Thirty'
Speaking of winning for the wrong movies, Jennifer Lawrence’s Oscar win for Silver Linings Playbook felt a bit like her goodwill from Winter’s Bone carrying over. Lawrence is one of the best actresses of her generation, to be sure, but Silver Linings Playbook is one of the more baffling awards contenders in recent memory, as it’s really just a perfectly fine romantic comedy. Still, voters were sparked by David O. Russell’s shift into “prestige” moviemaking, and Lawrence is consistently a phenomenal performer, so it’s not super hard to see why she won.
18 Julia Roberts – 'Erin Brockovich' (2000)
Who Should Have Won: Julia Roberts in 'Erin Brockovich'
Erin Brockovich both feels like the kind of movie they don’t make anymore and is an exciting twist on a well-trodden formula. That’s Steven Soderbergh for you. But Julia Roberts’ performance in this true story about a single mother fighting against a giant energy corporation on behalf of the people who have no means to fight is a fiery mix of moxie and compassion. The film itself holds up tremendously well, and at the time, Roberts was still trying to break out of the rom-com box that Hollywood had put her in. I’d say Erin Brokovich did the trick and gave us one of the most memorable Oscar acceptance speeches in the process.
17 Mikey Madison — 'Anora' (2024)
Who Should Have Won: Demi Moore in 'The Substance'
Sean Baker's Anora is a whirlwind, whipping through ideas and genres with ease, and the only one in this film that makes it from beginning to end is Mikey Madison's title character. It's an impressive ride that Madison has to match the spirit of at every step, be it the almost absurdly comical beginnings that make up the first act, or the devastatingly heartbreaking final moments. But Madison meets Baker's vision every step of the way, showing the young actress' incredible talents in every strange turn this film takes. Madison is a delight, and even when she's making what will clearly be terrible mistakes, we root for her and want the best for her. Anora is likely the first place many people will be introduced to Madison, but after her fantastic performance here, this feels like the beginning of a truly promising career just getting started.