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.
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. 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. 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.
25Sandra 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 Bullockis a terrific actress, but her win as a rich white woman who fosters a poor Black child overGabourey Sidibe’s gut-wrenching turn inPrecious– 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 intothe lawsuits and questionable conservatorshipthat 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, 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
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.
24Kate Winslet – ‘The Reader’ (2008)
Who Should Have Won: Meryl Streep in ‘Doubt’
Here is proof positive thatHarvey Weinstein’s influence on the Academy was extremely powerful. Up until the awards season that year,The Readerwas a bit of an “also-ran,” andKateWinsletwas considered a stronger candidate for her co-starring role inSam Mendes’ domestic dramaRevolutionary Road. But lo and behold, Weinstein managed not only to get Winslet a Best Actress nomination, but the film itself edged outThe Dark Knightfor a Best Picture nomination as well. And looking back, Oscar hostHugh Jackman’s opening number about not having seenThe Readerkind of says it all. Winslet isfineas a former Nazi concentration camp guard, butthis is nowhere near one of her best performances.
The Reader
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.
23Nicole Kidman – ‘The Hours’ (2002)
Who Should Have Won: Renée Zellweger in ‘Chicago’
AsMatt Damonsays inOcean’s Thirteen, the nose plays.Nicole Kidmanunderwent a pretty shocking physical transformation by wearing a false nose to play celebrated authorVirginia Woolfin the tryptic dramaThe 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 argueJulianne Mooregives the more memorable performance in the film, but Kidman is good and has a couple ofreally emotional scenes that played well to the Academy– especially at this particular time, when prestige dramas ruled the roost.
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.
22Meryl Streep – ‘The Iron Lady’ (2011)
Who Should Have Won: Viola Davis in ‘The Help’
The Iron Ladyis a very bad movie, butMeryl 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, andStreep nails the bombastic nature of Margaret Thatcherwhile also showing the controversial Prime Minister’s more emotional side here and there. Still, even thoughThe Helpis far from a great film,Viola Davis’ performance there felt a bit more complicated.
The Iron Lady
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.
21Jessica Chastain - ‘The Eyes of Tammy Faye’ (2021)
Who Should Have Won: Kristen Stewart in ‘Spencer’
By the timeJessica Chastainwon an Oscar forThe Eyes of Tammy Faye, she probably should’ve already had one. Chastain has been doing incredible work throughout the 21st century in films likeThe Tree of Life,Zero Dark Thirty, andTake Shelter, and the actress was long overdue for a win by 2021. While Chastain’s performance asTammy Faye Bakkermight not be her best role, it’s a testament to Chastain’s talents thatshe makes this performance not feel like a caricature.
The Eyes of Tammy Faye
An intimate look at the extraordinary rise, fall and redemption of televangelist Tammy Faye Bakker.
20Reese Witherspoon – ‘Walk the Line’ (2005)
Who Should Have Won: Reese Witherspoon in ‘Walk the Line’
The casting ofReese Witherspoonas June Carter-Cash was pitch-perfect, andthis performance still holds up as a fun, effective turnin the kind of music biopic that became so prevalent it turned into parody (literally, watchWalk Hard). She may not have a scene as intense as the one in whichJoaquin Phoenixbreaks 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
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.
19Frances 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 McDormandis certainly powerful inMartin McDonagh’s divisiveThree 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 – butMcDormand’s performance is still pretty excellent. And yet,Sally Hawkins’ wordless turn in the Best Picture winnerThe Shape of Waterprobably should’ve taken this one.
Three Billboards Outside Ebbing, Missouri
A mother personally challenges the local authorities to solve her daughter’s murder when they fail to catch the culprit.
18Jennifer 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 forSilver Linings Playbookfelt a bit like her goodwill fromWinter’s Bonecarrying over. Lawrence is one of the best actresses of her generation, to be sure, butSilver Linings Playbookis one of the more baffling awards contenders in recent memory, as it’s really just a perfectly fine romantic comedy. Still, voters were sparked byDavid O. Russell’s shift into “prestige” moviemaking, andLawrence is consistently a phenomenal performer, so it’s not super hard to see why she won.
Silver Linings Playbook
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.
17Julia Roberts – ‘Erin Brockovich’ (2000)
Who Should Have Won: Julia Roberts in ‘Erin Brockovich’
Erin Brockovichboth feels like the kind of movie they don’t make anymore and an exciting twist on a well-trodden formula. That’sSteven Soderberghfor you. ButJulia 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 isa 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 sayErin Brokovichdid the trick and gave usone of the most memorable Oscar acceptance speechesin the process.
Erin Brockovich
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.
16Mikey Madison — ‘Anora’ (2024)
Who Should Have Won: Demi Moore in ‘The Substance’
Sean Baker’sAnorais a whirlwind, whipping through ideas and genres with ease, and the only one in this film that makes it from beginning to end isMikey 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 to 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.Anorais likely the first place many people will be introduced to Madison, but after her fantastic performance here, this feels likethe beginning of a truly promising career just getting started.
Anora follows a young sex worker from Brooklyn who impulsively marries the son of a Russian oligarch, igniting a potential fairy tale. Upon learning of the union, his influential parents travel to New York to annul the marriage, jeopardizing her unexpected chance at a new beginning.
