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.
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 pigeonhole 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 are 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.
24 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 cringe-worthy, it’s 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.
The Blind Side
PG-13BiographyDocumentaryDramaSportThe story of Michael Oher, a homeless and traumatized boy who became an All-American football player and first-round NFL draft pick with the help of a caring woman and her family.
Release Date November 20, 2009 Director John Lee Hancock Cast Sandra Bullock , Tim McGraw , Quinton Aaron , Jae Head , Lily Collins , Ray McKinnon Runtime 12923 Kate Winslet – 'The Reader' (2008)
Who Should Have Won: Meryl Streep in 'Doubt'
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Here is proof positive 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 KateWinslet 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.
The Reader
RDramaDocumentaryRomancePost-WWII Germany: Nearly a decade after his affair with an older woman came to a mysterious end, law student Michael Berg re-encounters his former lover as she defends herself in a war-crime trial.
Release Date January 2, 2008 Director Stephen Daldry Cast Ralph Fiennes , Jeanette Hain , David Kross , Kate Winslet , Susanne Lothar , Alissa Wilms Runtime 12322 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 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.
The Hours (2002)
PG-13DramaThe story of how the novel "Mrs. Dalloway" affects three generations of women, all of whom, in one way or another, have had to deal with suicide in their lives.
Release Date December 27, 2002 Director Stephen Daldry Cast Nicole Kidman , Julianne Moore , Meryl Streep , Stephen Dillane , Miranda Richardson , George Loftus Runtime 110 minutes21 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. 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.
The Iron Lady
PG-13BiographyDocumentaryDramaHistoryAn elderly Margaret Thatcher talks to the imagined presence of her recently deceased husband as she struggles to come to terms with his death while scenes from her past life, from girlhood to British prime minister, intervene.
Release Date December 30, 2011 Director Phyllida Lloyd Cast Meryl Streep , Jim Broadbent , Susan Brown , Alice da Cunha , Phoebe Waller-Bridge , Iain Glen Runtime 10520 Jessica Chastain - 'The Eyes of Tammy Faye' (2021)
Who Should Have Won: Kristen Stewart in 'Spencer'
By the time Jessica Chastain won an Oscar in 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.
The Eyes of Tammy Faye
BiographyDrama
An intimate look at the extraordinary rise, fall and redemption of televangelist Tammy Faye Bakker.
19 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.
Walk The Line (2005)
PG-13BiographyDocumentaryDramaRomanceA chronicle of country music legend Johnny Cash's life, from his early days on an Arkansas cotton farm to his rise to fame with Sun Records in Memphis, where he recorded alongside Elvis Presley, Jerry Lee Lewis, and Carl Perkins.
Release Date September 13, 2005 Director James Mangold Cast Joaquin Phoenix , Reese Witherspoon , Ginnifer Goodwin , Robert Patrick , Dallas Roberts , Dan John Miller Runtime 13618 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.
Three Billboards Outside Ebbing, Missouri
RCrimeDocumentaryA mother personally challenges the local authorities to solve her daughter's murder when they fail to catch the culprit.
Release Date December 1, 2017 Director Martin McDonagh Cast Peter Dinklage , Caleb Landry Jones , Woody Harrelson , Sam Rockwell , Abbie Cornish , Kerry Condon Runtime 11517 Marion Cotillard – La Vie en Rose (2007)
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.
La Vie en Rose
PG-13BiographyBiopicMusicBiopic of the iconic French singer Édith Piaf. Raised by her grandmother in a brothel, she was discovered while singing on a street corner at the age of 19. Despite her success, Piaf's life was filled with tragedy.
Release Date June 22, 2007 Director Olivier Dahan Cast Marion Cotillard , Sylvie Testud , Pascal Greggory , Emmanuelle Seigner , Jean-Paul Rouve Runtime 140 minutes16 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 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.
Silver Linings Playbook
RComedyDocumentaryDramaRomanceAfter a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.
Release Date September 8, 2012 Director David O. Russell Cast Jennifer Lawrence , Robert De Niro , Bradley Cooper , Julia Stiles , Chris Tucker , Shea Whigham Runtime 12215 Julia Roberts – 'Erin Brockovich' (2000)
Who Should Have Won: Julia Roberts in 'Erin Brockovich'
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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 say Erin Brokovich did the trick, and gave us one of the most memorable Oscars acceptance speeches in the process.
Erin Brockovich (2000)
RBiographyDramaAn unemployed single mother becomes a legal assistant and almost single-handedly brings down a California power company accused of polluting a city's water supply.
Release Date March 17, 2000 Director Steven Soderbergh Cast Julia Roberts , Albert Finney , David Brisbin , Dawn Didawick Runtime 131 minutes14 Julianne Moore – 'Still Alice' (2014)
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 onset 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.
Still Alice
PG-13DramaDocumentaryA linguistics professor and her family find their bonds tested when she is diagnosed with Alzheimer's Disease.
Release Date December 5, 2014 Director Richard Glatzer , Wash Westmoreland Cast Julianne Moore , Kate Bosworth , Shane McRae , Hunter Parrish , Alec Baldwin , Seth Gilliam Runtime 10113 Hilary Swank – 'Million Dollar Baby' (2004)
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.
Million Dollar Baby
PG-13DramaDocumentarySportFrankie, an ill-tempered old coach, reluctantly agrees to train aspiring boxer Maggie. Impressed with her determination and talent, he helps her become the best, and the two soon form a close bond.
Release Date December 15, 2004 Director Clint Eastwood Cast Clint Eastwood , Hilary Swank , Morgan Freeman , Jay Baruchel , Mike Colter , Lucia Rijker Runtime 13212 Frances McDormand - 'Nomadland' (2021)
Who Should Have Won: Frances McDormand for 'Nomadland'
It's always a lovely surprise when the Academy Awards decide to go with a quieter, more introspective performance, which is exactly what they did in giving Frances McDormand her third Oscar with Nomadland. Chloé Zhao's gorgeous film is all about the beauty of the United States, but also the struggle of trying to get by in a country where many have taken to moving into their cars as a way to get by. Zhao fills her film with real-life nomads, and McDormand fits in perfectly as Fern, who is relatively new to this world of living in her van, but relishes the possibilities and opportunities it grants her. McDormand beautifully captures a feeling and a period in our history in a way that only a few actors could.
Nomadland
DramaFollowing the economic collapse of a company town in Nevada, a woman named Fern decides to sell most of her belongings and purchase a van to live and travel across the country. Along the way, she discovers a community of drifters, embracing the transient lifestyle and forming unbreakable bonds amidst the vast landscapes of America.
Release Date February 19, 2021 Director Chloé Zhao Cast Bob Wells , Swankie , Frances McDormand , Linda May , Derek Endres , David Straitham Runtime 107 Minutes11 Brie Larson – 'Room' (2015)
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 incredibly 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.
Room
RDramaPsychologicalHeld captive for years in an enclosed space, a woman (Brie Larson) and her young son (Jacob Tremblay) finally gain their freedom, allowing the boy to experience the outside world for the first time.
Release Date October 16, 2015 Director Lenny Abrahamson Cast Brie Larson , Megan Park , William H. Macy , Joan Allen , Amanda Brugel , Sean Bridgers Runtime 113 minutes10 Olivia Colman – 'The Favourite' (2018)
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.
The Favourite
RHistoryComedyIn early 18th-century England, the status quo at the court is upset when a new servant arrives and endears herself to a frail Queen Anne.
Release Date November 23, 2018 Director Yorgos Lanthimos Cast Olivia Colman , Rachel Weisz , Emma Delves , Faye Daveney , Emma Stone , Paul Swaine Runtime 120 minutes9 Renée Zellweger – 'Judy' (2019)
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.
Judy
PG-13DramaLegendary performer Judy Garland arrives in London in the winter of 1968 to perform a series of sold-out concerts.
Release Date September 27, 2019 Director Rupert Goold Cast Renée Zellweger , Jessie Buckley , Finn Wittrock , Rufus Sewell , Michael Gambon , Bella Ramsey Runtime 1188 Halle Berry – 'Monster's Ball' (2001)
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 and then falls in love with a racist executioner (I am not kidding this movie is insanely depressing).
monster's ball
RDramaRomanceAfter a family tragedy, a racist prison guard re-examines his attitudes while falling in love with the African-American wife of the last prisoner he executed.
Release Date June 7, 2001 Director Marc Forster Cast Billy Bob Thornton , Halle Berry , Taylor Simpson , Gabrielle Witcher , Heath Ledger , Amber Rules Runtime 111 minutes7 Emma Stone – 'La La Land' (2016)
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.
La La Land
PG-13MusicalDramaRomanceWhile navigating their careers in Los Angeles, a pianist and an actress fall in love while attempting to reconcile their aspirations for the future.
Release Date November 29, 2016 Director Damien Chazelle Cast Ryan Gosling , Emma Stone , Amiée Conn , Terry Walters , Thom Shelton , Cinda Adams Runtime 126 minutes6 Michelle Yeoh — 'Everything Everywhere All at Once' (2022)
Who Should Have Won: Michelle Yeoh in 'Everything Everywhere All at Once'
It's kind of nuts that Michelle Yeoh has never been nominated for an Oscar before, but Everything Everywhere All at Once gave the actress an opportunity to show everything she can do all at once—and the result is one of the best recent Best Actress wins. Yeoh plays Evelyn Wang, who discovers that she can travel between parallel universes while getting audited by the IRS. Yeoh's performance allows her to be an action master, a movie star, a hot-dog-fingered woman, a rock, and most importantly, a mother. Everything Everywhere All at Once asks for Yeoh to do a lot, and she does it all perfectly, while still pointing out just how insane this entire story truly is.
Everything Everywhere All at Once
RAdventureFantasyComedyDramaA middle-aged Chinese immigrant is swept up into an insane adventure in which she alone can save existence by exploring other universes and connecting with the lives she could have led.
Release Date March 25, 2022 Director Daniel Kwan , Daniel Scheinert Cast Jenny Slate , Michelle Yeoh , jamie lee curtis , Ke Huy Quan Runtime 139 minutes5 Cate Blanchett – 'Blue Jasmine' (2013)
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, CateBlanchett is 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.
blue jasmine
PG-13ComedyDocumentaryDramaA New York socialite, deeply troubled and in denial, arrives in San Francisco to impose upon her sister. She looks like a million dollars but isn't bringing money, peace or love.
Release Date August 1, 2013 Director Woody Allen Cast Cate Blanchett , Joy Carlin , Richard Conti , Glen Caspillo , Alec Baldwin , Charlie Tahan Runtime 98ncG1vNJzZmibn6G5qrDEq2Wcp51kr6a%2F02aYnKyimsC0ec6smpqqXay2r7rEq6pmqpGjuKawjGtorKxdmLKvwNSrsGg%3D