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'

Leigh Anne Tuohy looking at her rear view mirror while inside a car in The Blind Side
Image via Warner Bros. Pictures

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 Poster
The Blind Side
PG-13
Biography
Documentary
Drama
sport

The 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
129

Rent on Amazon

23 Kate Winslet – 'The Reader' (2008)

Who Should Have Won: Meryl Streep in 'Doubt'

Kate Winslett sitting in a courtroom in The Reader (2008)
Image via The Weinstein Company

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 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, 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 movie poster
The Reader
R
Drama
Documentary
Romance

Post-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
123

Watch on Prime

22 Nicole Kidman – 'The Hours' (2002)

Who Should Have Won: Renée Zellweger in 'Chicago'

Nicole Kidman as Virginia Woolf in 2002's The Hours.

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 movie poster
The Hours
PG-13
Drama
Documentary

The 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

Rent on Prime

21 Meryl Streep – 'The Iron Lady' (2011)

Who Should Have Won: Viola Davis in 'The Help'

Meryl Streep as Margaret Thatcher, standing in a crowd of people holding signs in The Iron Lady
Image via 20th Century Studios

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 movie poster
The Iron Lady
PG-13
Biography
Documentary
Drama
History

An 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
105

Watch on Peacock

20 Jessica Chastain - 'The Eyes of Tammy Faye' (2021)

Who Should Have Won: Kristen Stewart in 'Spencer'

Tammy Faye Bakker in bed in The Eyes of Tammy Faye
Image via Searchlight Pictures

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 Poster
The Eyes of Tammy Faye
Biography
Drama


An intimate look at the extraordinary rise, fall and redemption of televangelist Tammy Faye Bakker.

Release Date
September 17, 2021
Cast
Jessica Chastain , Vincent D'Onofrio , Andrew Garfield , Cherry Jones , Fredric Lehne , Sam Jaeger
Runtime
126

Rent on Amazon

19 Reese Witherspoon – 'Walk the Line' (2005)

Who Should Have Won: Reese Witherspoon in 'Walk the Line'

Joaquin Phoenix as Johnny Cash walking with Resse Witherspoon as June Carter In Walk The Line
Image via 20th Century Fox

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 movie poster featuring Joaquin Phoenix and Reese Witherspoon
Walk The Line
PG-13
Biography
Documentary
Drama
Romance

A 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
Runtime
136

Watch on Max

18 Frances McDormand – 'Three Billboards Outside Ebbing, Missouri' (2017)

Who Should Have Won: Sally Hawkins in 'The Shape of Water'

Frances McDormand as Mildred Hayes, standing by a billboard and looking sad in Three Billboards Outside Ebbing, Missouri
Image via Fox Searchlight Pictures

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 poster
Three Billboards Outside Ebbing, Missouri
R
Crime
Documentary

A 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
Runtime
115

Rent on Amazon

17 Marion Cotillard – La Vie en Rose (2007)

Who Should Have Won: Elliot Page in 'Juno'

Edith Piaf (Marion Cotillard) sings into a microphone on stage while wearing a black dress and a cross necklace.
Image via Icon Film Distribution

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 poster
La Vie en Rose
PG-13
Biography
Biopic
Music

Biopic 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 minutes

Rent on Amazon

16 Jennifer Lawrence – 'Silver Linings Playbook' (2012)

Who Should Have Won: Jessica Chastain in 'Zero Dark Thirty'

Tifanny and Pat meeting for the first time in Silver Linings Playbook
Image via The Weinstein Company

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 poster
Silver Linings Playbook
R
Comedy
Documentary
Drama
Romance

After 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
Runtime
122

Watch on Netflix

15 Julia Roberts – 'Erin Brockovich' (2000)

Who Should Have Won: Julia Roberts in 'Erin Brockovich'

Julia Roberts as Erin Brockovich sitting at her desk in Erin Brockovich.
Image via Columbia Pictures

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 Film Poster
Erin Brockovich (2000)
R
Biography
Drama

An 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 minutes

Watch on Netflix

14 Julianne Moore – 'Still Alice' (2014)

Who Should Have Won: Rosamund Pike in 'Gone Girl'

Julianne Moore and Kristen Stewart in Still Alice
Image via Sony Pictures Classics

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 poster
Still Alice
PG-13
Drama
Documentary

A 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
101

Watch on Max

13 Hilary Swank – 'Million Dollar Baby' (2004)

Who Should Have Won: Hilary Swank in 'Million Dollar Baby'

Hilary Swank in Million Dollar Baby
Image via New Line Cinema

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 Poster
Million Dollar Baby
PG-13
Drama
Documentary
sport

Frankie, 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
Runtime
132

Rent on Amazon

12 Frances McDormand - 'Nomadland' (2021)

Who Should Have Won: Frances McDormand for 'Nomadland'

Fern smiling and looking at the camera in 'Nomadland'
image via Searchlight Pictures

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
Drama

A woman in her sixties, after losing everything in the Great Recession, embarks on a journey through the American West, living as a van-dwelling modern-day nomad.

Release Date
January 29, 2021
Director
Chloé Zhao
Cast
Frances McDormand , Gay DeForest , Patricia Grier , Linda May , Angela Reyes , Carl R. Hughes
Runtime
108

Watch on Hulu

11 Brie Larson – 'Room' (2015)

Who Should Have Won: Brie Larson in 'Room'

Still of Brie Larson embracing Jacob Tremblay in Room movie

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-poster
Room
R
Drama
Documentary
Thriller

Held 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 minutes

Watch on Max

10 Olivia Colman – 'The Favourite' (2018)

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

Olivia Colman as Queen Anne in The Favourite
Image via Searchlight Pictures

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 movie poster
The Favourite
R
History
Documentary

In 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

Watch on Hulu

9 Renée Zellweger – 'Judy' (2019)

Who Should Have Won: Renée Zellweger in 'Judy'

Judy Garland singing on stage in Judy.
Image via 20th Century Studios

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-13
Drama

Legendary 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
Runtime
118

Watch on Prime

8 Halle Berry – 'Monster's Ball' (2001)

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

Billy Thornton and Halle Berry enjoy some ice cream in Monster's Ball.
image via Lions Gate

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 movie poster
monster's ball
R
Drama
Documentary
Romance

After 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

Watch on Prime

7 Emma Stone – 'La La Land' (2016)

Who Should Have Won: Emma Stone in 'La La Land'

Mia smiling at someone 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-poster
La La Land
PG-13
Musical
Comedy
Documentary
Drama
Romance

While 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

Rent on Amazon

6 Michelle Yeoh — 'Everything Everywhere All at Once' (2022)

Who Should Have Won: Michelle Yeoh in 'Everything Everywhere All at Once'

Evelyn protecting Joy and Waymond in Everything Everywhere All at Once.
Image via A24

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 Black and White Poster
Everything Everywhere All at Once
R
Adventure
Comedy

A 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
Cast
Jenny Slate , Michelle Yeoh , jamie lee curtis , Ke Huy Quan
Runtime
139 minutes

Watch on Netflix

5 Cate Blanchett – 'Blue Jasmine' (2013)

Who Should Have Won: Cate Blanchett in Blue Jasmine

Jasmine French smiling at someone off-camera in Blue Jasmine
Image via Sony Pictures Classics

Yes, Woody Allen sucks and yes, Blue Jasmine is very similar to A Streetcar Named Desire, but holy moly, Cate Blanchett 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 movie poster
blue jasmine
PG-13
Comedy
Documentary
Drama

A 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
98

Rent on Amazon