Winning actresses on a roll, took home gold
Since the turn of the century, the Oscars’ best actress category is one that has made quite a bit of history.
In 2002, “Monster’s Ball” lead Halle Berry became the first woman of color to take gold. And just last year, “Everything Everywhere All at Once” star Michelle Yeoh was named the first Asian best actress winner. Other victors have included icons (Meryl Streep, Cate Blanchett, Helen Mirren) plus young performers on the rise (Emma Stone, Jennifer Lawrence, Reese Witherspoon) who are now on the A-list.
Come March 10, Stone will either be a multiple Oscar winner, or a first-timer will join that high-profile company from the lineup of Annette Bening (“Nyad”), Carey Mulligan (“Maestro”), Sandra Hüller (“Anatomy of a Fall”) and Lily Gladstone (“Killers of the Flower Moon”).
Before the next woman is feted at the 96th Academy Awards, we’re ranking every best actress winner of the past 25 years:
25. Renee Zellweger, ‘Judy’ (2020)
The mediocre biopic is lifted by Zellweger’s portrayal of the iconic Judy Garland in the twilight of her career. The two-time Oscar winner captures Garland in showstopper mode and, with spine curved and cigarette in hand, deftly communicates Garland’s deteriorating state and the toll of her struggles with addiction.
24. Nicole Kidman, ‘The Hours’ (2003)
The psychological drama involves a day in the life of a trio of women over three different decades in the 20th century, all connected by Virginia Woolf’s novel “Mrs. Dalloway.” Sporting a prosthetic nose, Kidman plays the 1920s-era Woolf during a dark period, wrestling with her mental health while trying to finish her book.
23. Gwyneth Paltrow, ‘Shakespeare in Love’ (1999)
How did “Shakespeare” beat out “Saving Private Ryan” for best picture, you might ask? It helps that Paltrow is luminous as Viola, a much-needed muse (and secret lover) for William Shakespeare (Joseph Fiennes) as he fights writer’s block to fix “Romeo and Ethel, the Pirate’s Daughter” and make it something more classic.
22. Brie Larson, ‘Room’ (2016)
Before she was a superhero, Larson had a star-making turn as a supermom. Playing a young woman held in captivity for years with her 5-year-old son (Jacob Tremblay), Larson leaves no feeling unturned as she navigates trauma, parenting obstacles, sheer survival and the hard adjustment of returning to a world that moved on.
21. Hilary Swank, ‘Million Dollar Baby’ (2005)
A scrappy and ripped Swank got in the ring with Clint Eastwood (who also
directs) to play a waitress-turned-boxer in a sports drama that was more of a down note than any “Rocky” outing. Swank is feisty in the early rounds, and her portrayal is moving as her character is faced with extreme adversity.
20. Sandra Bullock, ‘The Blind Side’ (2010)
Based on a true story, the football flick showcases a deep playbook of Bullock’s talent: As Leigh Anne Tuohy, who adopts a foster teen who becomes a star lineman, Bullock goes all in on tough love, a bunch of warm hugs but also a mama-bear spirit when it comes to protecting her new charge. And while the real tale ended up being a bit sketchy, at least Bullock’s performance holds up.
19. Cate Blanchett, ‘Blue Jasmine’ (2014)
Blanchett delivers an enjoyably tragicomic turn in Woody Allen’s dramedy as a booze-swilling, Xanax-popping hot mess. Broke and suffering a nervous breakdown, the title character moves in with her sister (Sally Hawkins) and blows up her life, too, affecting relationships and finally ending up with the only person who’ll deal with her.
18. Meryl Streep, ’The Iron Lady’ (2012)
In the Margaret Thatcher biopic, Streep sports a stiff upper lip and no patience for snobby misogyny as England’s first female prime minister. The 21-time Oscar nominee – and arguably the best to ever do it – weaves a vulnerability into her imperious role as Thatcher rises from a lower-class outsider to ruler of the country during the tumultuous 1980s.
17. Julia Roberts, ‘Erin Brockovich’ (2001)
“Pretty Woman” made Roberts a star. This legal fable proved she also could be a thespian. In the true-life story, Roberts melded her comic and dramatic talents as a single mother who takes a stuffy law firm by storm and isn’t afraid to be a little flirty when taking on a utility company responsible for an environmental hazard.
16. Frances McDormand, ‘Nomadland’ (2021)
In Chloé Zhao’s road-trip drama, McDormand brings a mix of unbreakable steeliness, unconventional contentment and subtle vulnerability to Fern, a woman who travels the country and lives out of her white van after she loses her husband and her home.
15. Kate Winslet, ‘The Reader’ (2009)
While not a “Titanic” role per se, this multifaceted part let Winslet go deep in terms of emotion and historical intrigue. Her character Hanna enjoys a summer affair with a teenage boy (David Kross), who some years later is a law student horrified to find his brief love is now on trial for her war crimes as a Nazi guard at Auschwitz.
14. Reese Witherspoon, ‘Walk the Line’ (2006)
From the moment she hits the stage as singer June Carter – who has a meet-cute with future husband Johnny Cash (Joaquin Phoenix) – Witherspoon oozes effervescence. But she also plumbs a more dramatic side of her real-life musical figure, who has to weigh her romantic feelings against Johnny’s various addictions and vices.
13. Marion Cotillard, ‘La Vie en Rose’ (2008)
The French actress became a thing on this side of the Atlantic with her auspicious role in this musical biopic. Cotillard plays singer Edith Piaf with a wild-eyed passion through various episodes in the troubled chanteuse’s life, from musical high points and international fame to love affairs and drug-fueled mania.
12. Halle Berry, ‘Monster’s Ball’ (2002)
Still (and mind-blowingly) the only Black woman to win best actress in Oscar history, Berry de-glammed and got gritty in what remains her most powerful role to date. She plays a widow and troubled soul in a relationship with the corrections officer (Billy Bob Thornton) who, unbeknownst to her, oversaw her husband’s execution.
11. Hilary Swank, ‘Boys Don’t Cry’ (2000)
Swank won her first Oscar for playing Brandon Teena, a real-life transgender man who falls in love with a karaoke singer (Chloë Sevigny) but is the victim of a brutal hate crime. It was a remarkable performance in a romantic tragedy that shined a light on sexual identity years before it became a part of mainstream conversation.
10. Olivia Colman, ‘The Favourite’ (2019)
Director Yorgos Lanthimos blew up the stuffy period piece with this gonzo 18th-century comedy. Opposite talented co-stars such as Emma Stone and Rachel Weisz, Colman is a hoot as England’s mercurial Queen Anne, an insecure, gout-ridden royal who loves bunnies and freaking out on random servants.
9. Jessica Chastain,
‘The Eyes of Tammy Faye’ (2022)
Even with a makeup job and wardrobe that grow gaudier through the biopic, Chastain does a heavenly job playing real-life televangelist Tammy Faye Bakker. Her character sings, cries and endures a Greek tragedy of a downfall, but instead of being a caricature, Chastain finds the soul of a complex, good-hearted woman.
8. Charlize Theron, ‘Monster’ (2004)
In Patty Jenkins’ true-life crime thriller, Theron uncannily impresses as serial killer Aileen Wuornos, a prostitute who robs and kills men so she can provide for her girlfriend. It’s a complete physical embodiment, too, not only with extra weight and prosthetic teeth but also expressing the detailed body language and movements of a disturbed being.
7. Helen Mirren, ‘The Queen’ (2007)
A decade before “The Crown” was a thing, Mirren put her own indelible stamp on Queen Elizabeth II in a gripping historical drama set at the royal family’s darkest hour. In the wake of Princess Diana’s death in 1997, the queen tends to affairs privately yet butts heads with Prime Minister Tony Blair (Michael Sheen), who begs her to address the nation.
6. Emma Stone, ‘La La Land’ (2017)
Damien Chazelle’s old-school Hollywood musical is a romantic two-hander between Gosling’s jazz-loving musician and Stone’s struggling actress. She’s the heart of the piece, though, with a fabulous monologue and an overall performance that nicely taps into the themes of young unexpected love and bittersweet heartbreak.
5. Jennifer Lawrence, ‘Silver Linings Playbook’ (2013)
J.Law gives a sassy and stunning performance in David O. Russell’s joyously offbeat romantic dramedy as a young Philadelphia widow who meets a distressed Eagles fan (Bradley Cooper). They each struggle with mental illness, but a ballroom dance competition allows them to connect and find love and inner peace.
4. Julianne Moore, ‘Still Alice’ (2015)
A never-better Moore gives a top-notch, touching portrayal of a woman dealing with early onset Alzheimer’s in this drama. Playing the title role of a linguistics professor who faces changes and prepares her family for what’s to come as the disease takes hold, Moore navigates the character arc with honesty and heart-tugging empathy.
3. Michelle Yeoh, ‘Everything Everywhere All at Once’ (2023)
The sci-fi family kung fu adventure would have broken our collective brains if not for Yeoh’s heroic and grounded performance. As a laundromat owner who needs to save the multiverse, Yeoh breaks out all her moves, of both the emotional and action-flick varieties, and soars to make this wild tale way more personal than apocalyptic.
2. Frances McDormand, ‘Three Billboards Outside Ebbing, Missouri’ (2018)
“Fargo” fans might disagree, but this is McDormand’s finest (and most fiery) role. In Martin McDonagh’s darkly comic crime drama, she plays a woman whose daughter is raped and burned to death, and while the cops aren’t in a hurry to find justice, this tough mother is ready to torch her entire life if it means catching a killer.
1. Natalie Portman, ‘Black Swan’ (2011)
In Darren Aronofsky’s body horror ballet drama, Portman veers demonic and literally turns into a human swan. That’s dedication, people! Yet the actress brilliantly explores artistic obsession and a descent into madness playing a young ballerina in the lead role of “Swan Lake.” Surrounded by an overbearing mother (Barbara Hershey) and a talented rival (Mila Kunis), she wrestles with letting go of her repressed innocence, and Portman puts on a master class in unleashing one’s inner darkness.