Best Actress Winners of the 21st Century Ranked From Worst to Best

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 could change the course of a performer’s career. It could open doors to exciting new projects, allow an actor to be picky or choosy about what they do next, or – as it not entirely uncommon – it can turn out to not change a darn thing.

With all that in mind, in the wake of revisiting the past two decades of Best Actor Oscar winners, I thought it would be a fun exercise to go back and look at the Best Actress winners of the 21st century and rank each winning performance. In contrast to the Best Actor list, one common thread stood out: the Oscar-winning roles for women are far sadder and far less diverse than the Oscar-winning roles for men. There are outliers to be sure, but 15 of the 20 Oscar-winning roles on this list could fall into the “sad lady” category, contrasted with the Best Actor field which is more diverse in tone, genre, and frankly quality.

That’s not a reflection of the women included on this list, but of Hollywood’s tendency to pigeon-hole female characters into set templates. Things are getting better – as the years go on the roles get a bit more interesting – but it’s still a bit disheartening to see the same type of character over and over and over again.

With that said, there’s still a lot of genuinely incredible performances to be found on this list (and some not-so-incredible). 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.

RELATED: Every Best Actor Winner of the 21st Century Ranked From Worst to Best

20. Sandra Bullock – The Blind Side (2009)

Sandra Bullock The Blind Side
Image via Warner Bros.

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. But it’s not only the juxtaposition that makes this win kind of cringe-worthy, it’s really 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.

19. Kate Winslet – The Reader (2008)

Image via The Weinstein Company

Who Should Have Won: Meryl Streep in Doubt

Here is proof positive Harvey Weinstein’s influence on the Academy was in fact extremely powerful. Up until the awards season that year, The Reader was a bit of an “also-ran” and 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, Oscars host Hugh Jackman’s opening number about not having seen The Reader kind of says it all. Winslet is fine as a former Nazi concentration camp guard, but this is nowhere near one of her best performances.

18. Jennifer Lawrence – Silver Linings Playbook (2012)

Silver Linings Playbook Jennifer Lawrence Bradley Cooper
Image via The Weinstein Company

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 sparked to 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.

17. Nicole Kidman – The Hours (2002)

Nicole Kidman in The Hours
Image via Paramount Pictures

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 tryptic 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 she has a couple of really emotional scenes that played well to the Academy – especially at this particular time, when prestige dramas ruled the roost.

16. Meryl Streep – The Iron Lady (2011)

Image via The Weinstein Company

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. This is 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.

15. Reese Witherspoon – Walk the Line (2005)

Reese Witherspoon Walk the Line
Image via 20th Century Fox

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.

14. Frances McDormand – Three Billboards Outside Ebbing, Missouri (2017)

Image via Fox Searchlight

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 as 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.

13. Marion Cotillard – La Vie en Rose (2007)

Marion Cotillard La Vie En Rose
Image via Icon Film Distribution

Who Should Have Won: Elliot Page in Juno

It’s rare that a non-English performance wins one of the major trophies, but it’s hard to argue with Marion Cotillard’s win for the Édith Piaf biopic La Vie en Rose. Piaf’s life was tragic and sad, and this movie is indeed tragic and sad, but Cotillard finds compelling ways to imbue that sadness with a passion that is abundantly clear in Piaf’s art. Extra points for the retroactive Inception Easter egg.

12. Julia Roberts – Erin Brockovich (2000)

Image via Universal Pictures

Who Should Have Won: Julia Roberts in Erin Brockovich

Erin Brockovich both feels like the kind of movie they don’t make anymore, and 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 romcom box that Hollywood had put her in. I’d says Erin Brokovich did the trick, and gave us one of the most memorable Oscars acceptance speeches in the process.

11. Julianne Moore – Still Alice (2014)

Image via Sony Pictures Classics

Who Should Have Won: Rosamund Pike in Gone Girl

Still Alice had a curious road to the Oscars. The film premiered without a distributor at the 2014 Toronto International Film Festival, and critics hailed Julianne Moore’s performance as one that would almost be guaranteed to win the Oscar if a distributor picked it up. Sony Pictures Classics swooped in, bought it, and that’s exactly what happened – Moore steamrolled the awards season. It’s not hard to see why. She’s one of the best actresses of her generation, and her turn as a woman diagnosed with early on-set Alzheimer’s disease is absolutely devastating. There’s a part of me that still wishes Rosamund Pike had earned more recognition with her nasty turn in Gone Girl, but again, it’s hard to argue too strongly against this win here.

10. Hilary Swank – Million Dollar Baby (2004)

Hilary Swank Million Dollar Baby
Image via Warner Bros.

Who Should Have Won: Hilary Swank in Million Dollar Baby

Million Dollar Baby was an Oscar darling in 2004, picking up awards for Best Picture, Director, Supporting Actor, and of course Actress. And despite problems that folks might have with its twist and final act, Hilary Swank gives one hell of a performance that was wholly deserving of her second Oscar win. Swank plays an amateur boxer with a ton of heart and not a ton of finesse who is taken under the wing of a surly trainer (played by Clint Eastwood). Swank imbues the character with a tremendous amount of heart and fight, up through and including the film’s turn into more emotional territory in which Swank rises to some gut-wrenching challenges. This performance holds up.

9. Brie Larson – Room (2015)

room-brie-larson-jacob tremblay-05
Image via A24 Films

Who Should Have Won: Brie Larson in Room

Brie Larson was still fairly new to the scene when Room came out, having gained notice mostly for turning heads as Envy Adams in Scott Pilgrim vs. the World and for her incredible nuanced dramatic performance in the 2013 indie Short Term 12. But for Larson, there was before Room, and there was after Room. Her turn as a woman held against her will in a shed along with her young son is bold and inspiring and complicated, and Larson navigates the character’s strength in the face of abject hopelessness with ease. Moreover, her chemistry with the young Jacob Tremblay is absolutely terrific.

8. Olivia Colman – The Favourite (2018)

Image via Fox Searchlight

Who Should Have Won: Lady Gaga in A Star Is Born

Olivia Colman is absolutely fantastic in The Favourite… but it’s a supporting role. This is one of those times that the studio saw an easier path to victory in Best Actress than Best Supporting for the film’s showiest performance and took it – and they won! I love The Favourite, but that story is told through Emma Stone’s eyes, and she’s the true lead. But taking this at face value, Colman’s performance as the emotionally stunted Queen Anne is a hoot, vacillating between laugh-out-loud comedy and heartbreaking sadness. Watching Colman here is like watching a great magician at work; you can’t figure out how she does it, but you’re absolutely wowed by the effort and effect.

7. Emma Stone – La La Land (2016)

Image via Summit Entertainment

Who Should Have Won: Emma Stone in La La Land

Yes it’s been memed to death, yes the jazz stuff is silly, but I don’t care, La La Land is a great film and Emma Stone is fantastic in it. A rarity on this list is fictional characters, as the Academy is far more eager to single out impersonations or imitations of real-life people, which makes the degree of difficulty for Stone that much harder. La La Land is a dramatic romance about the many paths ahead of us in life, and what we sacrifice for the paths we choose. Stone’s performance as an aspiring actress who falls in love with an aspiring jazz musician is fully formed, combining lonesomeness and passion and optimism and hopelessness all in one. The film simply doesn’t work if this character doesn’t work, and Stone makes it sing.

6. Renée Zellweger – Judy (2019)

Image via LD Entertainment and Roadside Attractions

Who Should Have Won: Renée Zellweger in Judy

There are plenty of times in Oscar history where a performer or director or film “based on a real person” wins simply for being a solid imitation and reminding audiences of the thing they love (ahem Bohemian Rhapsody ahem). Judy is not one of those films. Renée Zellweger’s performance as Judy Garland towards the end of her life goes beyond imitation. She gets the voice and mannerisms right to be sure, but she also understands the emotions and the history that were driving Garland. There’s intent behind the impersonation, and it makes all the difference.

5. Halle Berry – Monster’s Ball (2001)

Halle Berry Monsters Ball
Image via Lionsgate Films

Who Should Have Won: Halle Berry in Monster’s Ball

Boy Monster’s Ball is simply one of the most depressing movies ever made, isn’t it? To be frank I had not seen this movie before making this list, and it turns out there was a good reason for it – it’s a (kinda) romantic drama in which terrible thing after terrible thing occurs and it is depressing as heck. But Halle Berry’s history-making Oscar-win was well-deserved, as it could not have been easy to fill the role of a waitress who suffers two devastating losses in a short period of time and then falls in love with a racist executioner (I am not kidding this movie is insanely depressing).

4. Helen Mirren – The Queen (2006)

Helen Mirren The Queen
Image via Pathe

Who Should Have Won: Helen Mirren in The Queen

The Queen is kind of a prototype for what screenwriter Peter Morgan would later create with the Netflix series The Crown, but Helen Mirren is so good in it that Imelda Staunton will have some big shoes to fill when it comes time to cover the same events in the Netflix series. What Mirren gets so right here is that the stoicism of Queen Elizabeth II doesn’t necessarily mean she’s unfeeling. But knowing what she went through, where she came from, and how she felt about Princess Diana colors her reaction to Diana’s death, and it’s a testament to Mirren’s strength as a performer that she’s able to convey those complicated emotions through the Queen’s calm and measured demeanor. For once, this is a case of the Academy recognizing that sometimes less is more.

3. Natalie Portman – Black Swan (2010)

Image via Fox Searchlight Pictures

Who Should Have Won: Natalie Portman in Black Swan

Not since Black Swan has a movie as weird as Black Swan done this well in this category, which makes Natalie Portman’s win all the more impactful. Darren Aronofsky’s film is a full-on psychological thriller, drawing inspiration from classic 70s thrillers while expanding into avenues both rich and fantastical to build out this story of a dancer competing for a coveted role in a ballet. Portman navigates Aronofsky’s twisty approach with ease, never quite tipping her hand too hard one way or another, culminating in a jaw-dropping finale during which Portman absolutely sticks the landing.

2. Charlize Theron – Monster (2003)

Image via Paramount Pictures

Who Should Have Won: Charlize Theron in Monster

Every once in a while an actor will give a performance so full-bodied, so possessed that “unrecognizable” ceases to be hyperbolic and becomes literal. That’s what Charlize Theron did in Patty Jenkins’ 2003 crime drama Monster, in which she fully disappeared into the role of serial killer Aileen Wuornos. The performance goes beyond the moniker attached to Wuornos, as Theron digs deep into the character’s psyche to create a complicated, conflicted character with whom we’re able to if not fully empathize, at least understand. It’s an incredibly difficult task to accomplish, and it’s a testament to both Theron and Jenkins that Monster works as well as it does. A truly unforgettable performance.

1. Cate Blanchett – Blue Jasmine (2013)

Image via Sony Pictures Classics

Who Should Have Won: Cate Blanchett in Blue Jasmine

Yes Woody Allen sucks and yes Blue Jasmine is very similar to A Streetcar Named Desire, but holy moly is Cate Blanchett incredible in this movie. Blanchett, again, is one of the best actresses working today, and Blue Jasmine is one of her finest performances yet. She plays a formerly rich socialite who is forced to move to her working class sister’s apartment in San Francisco, boozing her way through a complete and total nervous breakdown. The performance is magnificent, packed with little nuances that make the character all the more rich and full-bodied. At turns hilarious and devastating, this is one of the best onscreen performances of the 21st century full-stop.

KEEP READING: Every Best Picture Oscar Winner Ranked

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