Best Actress Oscar-Winners of the 21st Century, Ranked Worst to Best

Meryl Streep is her generation’s greatest actress — hell, she might be the finest actress of several generations. But that doesn’t mean the masters can’t have their missteps; what’s inexcusable is for the Academy not to recognize it as such. As Margaret Thatcher, the former British Prime Minister now coping with old age and inactivity, Streep delivers a caricature where a performance ought to go. The Iron Lady is a shockingly uninspired biopic across the board, failing to grasp this influential, divisive leader’s steeliness or wit, and the script’s lack of insight brings out Streep’s worst quality, flaunting technique over feeling.

One of the dominant storylines of the 2010 Oscar season was the comeback story of Sandra Bullock, the onetime marquee draw who had stumbled in the early 2000s, only to regain her footing thanks to a rom-com hit (The Proposal) and some of the best reviews of her career for The Blind Side. That feel-good narrative fueled her Oscar win, but with perspective it’s clear that her performance as the no-nonsense Leigh Anne Tuohy is little more than a folksy amusement without a lot of depth behind it. And her role actually underlines what’s wrong with the movie: It’s another Hollywood tale of how a privileged white character learns valuable lessons by helping a poor black youth.

From 1999 to 2004, Nicole Kidman was arguably the world’s best actor, working with top-notch fillmakers and lining up a string of career-defining performances: Eyes Wide Shut, Moulin Rouge, The Others, Dogville, Birth. By comparison, the role that won her an Oscar, the melancholy author Virginia Woolf in The Hours, is merely good — flecked with sadness and desperation and steel, but also weighed down by the ponderous solemnity that director Stephen Daldry always brings to his work. In other words, Kidman’s low placement on this list is less an indictment of her performance than an indication of the glassy film for which she won. For plenty of other actors, The Hours would have been their high-water mark.

In a 2005 episode of the Ricky Gervais series Extras, Kate Winslet famously played a satirical, craven version of herself who’s starring in a Holocaust movie because “[you’re] guaranteed an Oscar.” A few years later, she ended up winning an Oscar playing a 1950s German woman who begins a relationship with a teenager (David Kross) … and, oh yeah, was also complicit in the perpetuation of the Holocaust. Was it coincidence? “This was never a Holocaust movie to me,” she said at the time about The Reader. “That’s part of the story and provides something of a backdrop … But to me it was always an extraordinarily unconventional love story.” Fair enough, but its genteel tastefulness was so stuffy that it made it hard to believe that anybody would have been involved with this project except to make a play for awards. Winslet is predictably heartrending in the role, but ultimately it’s a forgettable part in a forgettable film.

When Tammy Faye Bakker was alive, she was often lampooned; the media fixated on her heavily-made-up face and slightly zoned-out demeanor. Jessica Chastain won an Oscar by trying to correct that cultural impression, turning her from a cartoon character into a vulnerable, searching soul, clinging to her dignity while her greedy, philandering husband Jim (Andrew Garfield) focused on building his televangelist empire. One of her generation’s finest actors, Chastain played Tammy Faye with intelligence and compassion, nailing the woman’s eccentricities — not to mention the pain underneath that plastered-on smile and aggressively cheery voice. Academy voters responded to the convincing physical transformation, but The Eyes of Tammy Faye too easily fit the biopic mold, the film more intent on recreating Tammy Faye’s look than really exploring her psyche. As a result, this is one of Chastain’s showiest turns…but far from her best.

What’s strongest about Zellweger’s performance as the doomed Judy Garland is how the two-time Oscar-winner seems to be communicating something about herself within her reverent portrayal of the legendary singer. Judy chronicles Garland’s swan song as, near the end of her life, she traveled to London for a series of concerts designed to be her comeback. Beyond nailing the icon’s inflection and wit, Zellweger articulates the mindset of being a woman working in a sexist entertainment industry. And like The Wizard of Oz star, the actress was trying to prove to her doubters that her best years weren’t behind her. (Garland died at age 47; Zellweger was 50 when she claimed her Judy Oscar.) This is familiar biopic fare in a lot of ways, but the compassion that she brought to the role helps elevate the proceedings. Zellweger seems to be striking a blow for “women of a certain age” who aren’t ready to be put out to pasture — even if, in Garland’s case, an overdose cut her life tragically short.

“Stand By Your Man” was a Tammy Wynette song, but it could have just as easily applied to Walk the Line‘s June Carter, who loved Johnny Cash but feared what his drinking and restlessness might bring to her life. Reese Witherspoon embodies those mixed emotions in this biopic that doubles as a romantic drama, and she does it with a no-bullshit frankness that keeps Joaquin Phoenix’s Cash on his toes. Like several of the Best Actress winners on this list, Witherspoon has been stronger and subtler in other roles, but Walk the Line provided her lively, down-to-earth persona with its most award-worthy platform.

“I don’t know what I did in this life to deserve all this,” Hilary Swank said when accepting her Oscar for Million Dollar Baby. “I’m just a girl from a trailer park who had a dream.” In that way, she was very closely aligned to her character Maggie, who escapes dead-end Missouri to get to Los Angeles to train with Clint Eastwood’s cranky gym owner and become a champion boxer. This was Swank’s second Oscar after 1999’s Boys Don’t Cry, and in both movies she transcends the cliché descriptors usually used to praise her performances: grit, spunk, pluck. The Academy Awards have had a long history of celebrating underdogs, and here Swank honed in on Maggie’s nowhere-else-to-go desperation, barreling through, over and under any obstacle that will keep her from finding some sense of contentment. Which only makes the cruel twist of fate that visits her character all the more senseless and tragic.

Moviegoers had seen Marion Cotillard in films such as Big Fish and A Good Year, but they hadn’t really seen her until she played the momentously troubled Edith Piaf in La Vie en Rose. This is a music biopic that throws chronology out the window, preferring thematic connections to a straight recounting of events, and Cotillard’s performance is equally adventurous, playing the singer as a tumultuous talent whose passions both fed her artistry and destroyed her. Since Rose, Cotillard has often played bewitching, heartbreaking love interests in American films, but the rawness she brought to 2014’s Two Days, One Night proves that Piaf’s fluid pain is something she can access when the right role requires it.

In another time, under different circumstances, maybe Aileen Wuornos’s life wouldn’t have turned out so tragically — maybe she wouldn’t have brought such misery to so many who crossed her path. But this is the world we live in, and Monster unsparingly depicts this serial killer and prostitute in all her torment and anger. But what made you care was Charlize Theron’s eye-opening performance. It’s very easy to dismiss her Oscar win — just one more glamorous actress burying herself in unattractive makeup to prove her dramatic bona fides, right? But that doesn’t explain the depth of anguish Theron brought to the role, the sense of active wrestling within Wuornos’s head as she tries to make a life with a new lover (Christina Ricci) while killing her johns in a misguided attempt to cope with the abuse she suffered as a child. Theron isn’t interested in explaining Wuornos, which makes Monster all the most unsettling: It’s very possible Wuornos herself couldn’t grapple with the mess of demons swirling inside her.

For us folks who’d been following Brie Larson’s career in indie films like Short Term 12 and noticed how she could slyly steal scenes in supporting roles (see Rampart, Don Jon and the Jump Street movies), we knew it would only be a matter of time before she was recognized as a major talent by voters. The surprise was that it happened this quick for the young actress – but really, how many times does a plum role like Room‘s resident hostage/loving mother come around? And how many performers could have lent such grace and maternal grit to the part while also being the perfect screen partner to the equally intense Jacob Tremblay? It was more than a win — it was an A-list coronation for an actress who went on to become one of the biggest MCU superheroes as Captain Marvel.

More than 20 years after winning her first Best Actress prize for Fargo, Frances McDormand returned to the winner’s circle for her portrayal of Mildred Hayes, a mourning mother who wants justice for her slain daughter. Three Billboards Outside Ebbing, Missouri gave the actress a terrific platform for her flinty, no-fucks-given persona. But McDormand never let you forget the character’s terrible anguish — or her gnawing realization that finding her child’s killer can’t possibly heal the mortal wound to her psyche. That she could also make Mildred so funny was merely the icing on the cake. Tough but also surprisingly tender, the performance bravely anchors a movie about our self-destructive need to meet violence with violence — and those rare occasions when we allow compassion and forgiveness to enter into the equation.

When J.Law hysteria was at a fever pitch, it could be easy to forget what inspired all the hoopla in the first place. Revisit Silver Linings Playbook, however, and the reasons for the young actress’s ascension become abundantly clear. Lawrence plays Tiffany, a recent widow who’s mourning her dead husband and battling ongoing issues with depression. That describes the character, but not the way Lawrence portrays her, which is as a combustible, brittle woman who doesn’t know whether she’s coming or going. Tiffany is empowered by her attractiveness and sexuality, but she’s also afraid of what falling in love with a new man (Bradley Cooper) might mean. It’s not often that the movies produce a “troubled” character this layered and vibrant, and Lawrence’s livewire performance typifies what’s so tremendous about her acting. It feels urgent, compelling and lifelike without ever feeling fussed-over or a fluke.

After all the furor died down around La La Land — Was it escapist pap, or a deft, melancholy salute to the challenges of balancing art and love? Was it too much of a back-patting Hollywood throwback in the year of Moonlight? Did Ryan Gosling really save jazz? — what remained was Emma Stone’s performance as Mia. The big screen has been filled with stories of dreamers moving to Los Angeles to make their name, but Stone encapsulated them all in her giddy, dorky enthusiasm and sweet demeanor. Here’s a character whose optimism is boundless, and you fear what will happen if the cruel crush of reality ever knocks her down. It’s not easy to portray an indomitable spirit, but Stone reveals all the courage and faith that go into believing in love and dreams. She puts a song in your heart and a lump in your throat.

“I don’t really think about anything too much,” Olivia Colman told Rolling Stone while trying to explain her approach to playing Queen Anne in Yorgos Lanthimos’ biting, oddly touching period comedy. “My book on acting would be very short.” The English actress may have trouble articulating what she brought to the role, but it was clear enough to anyone who saw how she gave us a foolish, sickly, vulnerable leader who we both mocked and felt inordinately bad for. Colman had made a career in British television as an ace comedienne (Peep Show) and deft dramatic presence (Broadchurch), but it wasn’t until The Favourite that moviegoers — and especially American audiences — got to see her combine both talents. As the object of affection for two very different women (previous Oscar-winners Rachel Weisz and Emma Stone), Queen Anne quickly learns just how lonely it is at the top. But when Colman won the Academy Award in an upset over The Wife‘s Glenn Close, her triumph was joyously received in the room — a culmination of a stellar, still-vibrant career capped by some of the very best work she’s ever done, on the big or small screen.

Because Halle Berry had mostly done comedies and X-Men movies before Monster’s Ball, it’s possible that her Oscar triumph was partly a surprised reaction from some Academy voters that she had such dramatic chops. But that patronizing attitude doesn’t do justice to what’s an exceedingly raw portrayal of Leticia, a working-class Georgian who loses both her husband and son over the course of the film, falling into an ill-advised love affair with Billy Bob Thornton’s racist prison guard. (The buildup to their intense, fumbling sex scene — in which Leticia begs him to “make me feel good” — remains one of the century’s most intimate, visceral mergers of pain and release.) Berry plays her with such wounded pride that it’s almost too much to take, and in a time of #OscarsSoWhite, it’s worth pointing out that she’s still the only African-American to ever win Best Actress.

Undertaking a year of ballet training to prepare for her Black Swan role, Natalie Portman delivers a worst-case/best-case scenario of an artist’s need to push herself beyond her breaking point to make something that lasts. Both the beauty and the madness inherent in pursuing perfection is written all over the actress’s face, resulting in the sort of go-for-broke portrayal that leaves you in thrall, even if you remain fearful that the woman giving the performance might break in the process. But Portman never wavered: In a career that began with the icy confidence witnessed in The Professional, Black Swan was the culmination of the delicate/steely juxtaposition that is often at the heart of the characters she plays. This psychological thriller often risks flying right off the rails, but Portman gives the movie its empathetic grounding.

What does a slow-motion nervous breakdown look like? In our worst nightmares, we fear it resembles Cate Blanchett’s comic/tragic portrayal of the recently widowed Jasmine in Woody Allen’s dark comedy, which stands back with a mixture of restraint and horror as it observes a woman’s painful unraveling. Blanchett has never been one to hide her characters’ tics and mannerisms, but as Jasmine, who is trying to rebuild her life in San Francisco after some unfortunate circumstances in New York, the role requires an endless, fascinating litany of fried nerves, frantic justifications and barely-held-together posturing, combining to dramatize a life inexorably circling the drain. Winning her second Oscar, Blanchett is volcanically funny at times, but we never quite laugh at Jasmine: Her mental collapse is so complete that it’s harrowing to watch.

Often, actors win Oscars for showing their serious side, in the process stripping away the joy and buoyancy that made audiences fall in love with them in the first place. Their suffering — the withholding of the thing that makes them so magnetic — is meant to suggest the lengths they’ll go for their art. And then there’s Michelle Yeoh, who took home Best Actress for finally finding a role that captured all the aspects of her brilliance. Martial-arts mastery mixes with crack comic timing mixes with poignant understatement in her portrayal of Evelyn, an unhappy wife and mother whose bad day goes even more haywire once she learns she’s the chosen one destined to defeat the forces of evil. Everything Everywhere All at Once’s multiverse allowed Yeoh to be many different Evelyns, each of them tapping into another side of the actor’s graceful, deadpan, acrobatic self. In some other universe, Hollywood would have given this Hong Kong-cinema icon a career full of such intricate, rewarding characters. Alas, we live in this one, but it was worth the wait.

Stars matter: Rarely has that been truer than when Julia Roberts locked onto the story of Erin Brockovich, a struggling single mother who helped fight for a small Southern California community that had been slowly poisoned by a Goliath energy corporation. This is not to suggest that Erin Brockovich isn’t a smart, moving tale, but it’s Roberts’ natural likability, brassiness and sex appeal that continually elevate the material. (Indeed, this may be the one Steven Soderbergh film that belongs more to its lead than to the director.) Telling off corporate bigwigs, squaring off with a possible love interest (Aaron Eckhart) and hurling magnificent amounts of attitude at Albert Finney’s befuddled boss, Roberts doesn’t so much embody a role as she perfects her persona.

When Nomadland was announced as Best Picture at the 2021 Academy Awards, director Chloé Zhao ended her acceptance speech by bringing Frances McDormand to the microphone, saying, “Now, I give you … Fern.” McDormand pushed back on that introduction — “No, I’m not, I’m Fran” — but you could understand Zhao’s intention. McDormand, who also served as a producer on Nomadland, was the film’s emotional center; she didn’t just play the movie’s wandering widow so much as imbue the story with its tough-love, no-bullshit sensibility. There’s a raw immediacy to the performance that allows zero sentimentality to sneak through, conveying a character awash in grief but also curiosity and resilience. McDormand doesn’t show us everything about Fern — appropriate for a character so guarded and flinty — but we learn enough. If McDormand never acted again, it would have been a stunning culmination to a singular career. Thankfully, like her character, she’s just kept on truckin’.

The defining quality of Helen Mirren’s performance as Queen Elizabeth II is its stillness. And it’s in that quiet command that the actress sums up all that’s admirable and also antiquated about the British Monarchy: its constant, comforting continued existence, as well as its blinkered myopia. That’s a tricky balance, but Mirren walks it perfectly in The Queen, a seemingly straightforward docudrama about the 1997 death of Princess Diana that peeks behind the curtain to see the inner workings of a woman who had reigned, by that time, for 45 years. Neither a straight facsimile nor a nervy reimagining of one of the world’s most famous public figures, Mirren prefers to let Elizabeth remain a withdrawn, restrained presence, hinting at her casual callousness but also suggesting a queen who’s seen enough history pass to never be surprised by anything that occurs. Mirren has often carried herself with a regal air, but The Queen was her crowning achievement.

In 1995, Julianne Moore, still relatively unknown at the time, essayed one of the great modern film roles in Safe, playing a suburban housewife who’s allergic to the world, a condition that results in her practically disappearing in front of our eyes. Almost 20 years later, now firmly established as one of our best actresses, Moore delivered another astounding performance about a different woman losing herself. Still Alice tells the story of a linguistics professor diagnosed with early-onset Alzheimer’s, and the actress plays her as a bright, poised 50-year-old who quickly learns that her intelligence can’t save her from a disease that will ravage her memory. It’s a performance that’s powerfully internal yet expressed with incredible physicality: The woman’s fear, resignation and anger come through in Moore’s panicked, anguished eyes, but what’s especially remarkable is how she articulates the emptying out of a once-vibrant person. Alice is still there, and yet she’s not, and the star honors the mysteries of a body that’s lost its inner light and yet retained its ineffable soul.