Brit + Co Logo

Only 3 women have won Best Actress twice since 1999—can you name them all?

Every Best Actress Oscar Winner & Their Iconic Gowns Since 1999 (From Gwyneth to Now)

oscars best actressed
Getty

We’re all about celebrating incredible women on-screen and off, so the Best Actress race at the Oscars is one of our favorite categories to watch every awards season. This year’s nominees continue a long legacy of powerhouse performances from women whose work has shaped the film industry for nearly a century.

We’ll find out soon enough whose name will be etched onto the 2026 trophy, but in the meantime, here’s a look back at the Best Actress Academy Award winners of the past 27 years!


Here are the Best Actress Academy Award winners since 1999!

Four women holding Oscars, standing against gold statuettes backdrop.

Getty

This year’s nominees — Jessie Buckley (Hamnet), Rose Byrne (If I Had Legs I’d Kick You), Kate Hudson (Song Sung Blue), Renate Reinsve (Sentimental Value), and Emma Stone (Bugonia) — join these iconic performers as the few lucky and talented enough to earn the big honor. We're so excited to watch the 98th Academy Awards (Oscars 2026) this Sunday, March 15, starting at 7 p.m. ET / 4 p.m. PT, with the red carpet show beginning earlier. The event will be hosted by Conan O'Brien and broadcast on ABC.

Mikey Madison, 2025

Getty

Mikey Madison, 2025

Madison scored her first Oscar for her breakout performance in Anora. Playing the title character—a young sex worker swept into a whirlwind, Cinderella-like romance—she delivered a striking performance that helped the indie film become one of the biggest winners of the night.

Emma Stone, 2024

Getty

Emma Stone, 2024

Stone won her second Oscar for her fearless performance in Poor Things. Playing Bella Baxter, a woman discovering the world on her own terms, Stone delivered a wildly inventive and physically daring performance that became one of the year’s most talked-about roles.

Michelle Yeoh, 2023

Getty

Michelle Yeoh, 2023

Yeoh made history with her Oscar-winning performance in Everything Everywhere All at Once. Her role as Evelyn Wang—a woman navigating family struggles across the multiverse—blended action, comedy, and emotional depth in a truly unforgettable performance.

Jessica Chastain, 2022

Getty

Jessica Chastain, 2022

Chastain earned her first Oscar for her dazzling transformation into televangelist Tammy Faye Bakker in The Eyes of Tammy Faye. Beneath the bold makeup and big hair, she delivered a heartfelt performance that captured Tammy Faye’s empathy and resilience.

Frances McDormand, 2021

Getty

Frances McDormand, 2021

McDormand won her third Oscar for her quietly powerful performance in Nomadland, directed by Chloé Zhao (who also won Best Director that year). Playing a woman navigating life on the road after personal loss, her understated, deeply human role anchored the film’s meditative tone.

\u200bRen\u00e9e Zellweger, 2020

Getty

Renée Zellweger, 2020

Zellweger took home the Oscar for her transformative performance as legendary entertainer Judy Garland in Judy. Her emotional portrayal of the icon’s final years reminded audiences why she’s one of Hollywood’s most compelling actors.

Olivia Colman, 2019

(Photo via Kathy Hutchins/ Shutterstock)

Olivia Colman, 2019

Colman won her first Oscar last year for her royal performance in The Favourite and we couldn't have loved her acceptance speech more.

Frances McDormand, 2018

(Photo via Jeff Kravitz/FilmMagic)

Frances McDormand, 2018

McDormand won her second Best Actress Oscar for her role as Mildred Hayes in Three Billboards Outside Ebbing, Missouri.

Emma Stone, 2017

(Photo via Frazer Harrison/Getty Images)

Emma Stone, 2017

The La La Land star's song-and-dance skills — not to mention her chemistry with costar Ryan Gosling — got the Academy's vote in 2017.

Brie Larson, 2016

(Photo via Jason Merritt/Getty Images)

Brie Larson, 2016

Larson earned raves (and an Oscar) for her moving performance in the 2015 movie Room.

Julianne Moore, 2015

(Photo via Jason Merritt/Getty Images)

Julianne Moore, 2015

After two previous Best Actress nominations for Far From Heaven and The End of the Affair, Moore won the Oscar for Still Alice, in which she played a woman grappling with the devastating effects of early-onset Alzheimer's.

Cate Blanchett, 2014

(Photo via Jason Merritt/Getty Images)

Cate Blanchett, 2014

Blanchett, who also has a Best Supporting Actress Oscar from 2005, won her second Academy Award for Blue Jasmine.

Jennifer Lawrence, 2013

(Photo via Jason Merritt/Getty Images)

Jennifer Lawrence, 2013

Two years after receiving her first Oscar nomination (for Winter's Bone), Lawrence took home a trophy for her work in the David O. Russell romantic dramedy Silver Linings Playbook, which costarred Bradley Cooper.

Meryl Streep, 2012

(Photo via Jason Merritt/Getty Images)

Meryl Streep, 2012

Streep, who has a record 21 Oscar nominations to her name, has won the Best Actress Academy Award twice, including in 2012, for her portrayal of Margaret Thatcher in The Iron Lady.

Natalie Portman, 2011

(Photo via Jason Merritt/Getty Images)

Natalie Portman, 2011

Portman had to go to some pretty dark places for her Oscar-winning turn in 2010's ballet drama Black Swan.

Sandra Bullock, 2010

(Photo via Jason Merritt/Getty Images)

Sandra Bullock, 2010

Bullock won for her portrayal of Leigh Anne Tuohy in The Blind Side, which was based on the true story of NFL player Michael Oher.

Kate Winslet, 2009

(Photo via Jason Merritt/Getty Images)

Kate Winslet, 2009

Winslet has seven Oscar nominations under her belt, including one win for her performance in The Reader, which was based on the 1995 German novel of the same name by Bernhard Schlink.

undefined

(Photo via Vince Bucci/Getty Images)

Marion Cotillard, 2008

Cotillard, who took home the Oscar for her portrayal of Edith Piaf in La Vie en Rose, is the only French actress to win this category for a French-language performance.

Helen Mirren, 2007

(Photo via Vince Bucci/Getty Images)

Helen Mirren, 2007

Mirren was nominated twice for supporting roles — in Gosford Park and The Madness of King George — before she won the Best Actress category for playing Queen Elizabeth II in The Queen.

Reese Witherspoon, 2006

(Photo via Jeff Vespa/WireImage)

Reese Witherspoon, 2006

Witherspoon gave one of the best performances of her career — if not the best — as June Carter in the Johnny Cash biopic Walk the Line.

Hilary Swank, 2005

(Photo via M. Von Holden/FilmMagic)

Hilary Swank, 2005

Swank's win for her portrayal of an aspiring boxer in Clint Eastwood's Million Dollar Baby was her second victory in this category.

Charlize Theron, 2004

(Photo via Jeffrey Mayer/WireImage)

Charlize Theron, 2004

Wonder Woman filmmaker Patty Jenkins directed Theron's Oscar-winning turn in 2003's Monster, a biographical crime drama about serial killer Aileen Wuornos.

Nicole Kidman, 2003

(Photo via Frank Micelotta/Getty Images)

Nicole Kidman, 2003

Kidman gave an Oscar-worthy performance as Virginia Woolf in The Hours, which costarred Meryl Streep and Julianne Moore and was based on Michael Cunningham's Pulitzer Prize-winning novel of the same name.

Halle Berry, 2002

(Photo via Frederick M. Brown/Getty Images)

Halle Berry, 2002

Thanks to her performance in Monster's Ball, Berry made Oscars history by becoming the first Black woman to win the Academy Award for Best Actress.

Julia Roberts, 2001

(Photo via Chris Weeks/Getty Images)

Julia Roberts, 2001

Like a lot of other stars on this list, Roberts won for her portrayal of a real person — in this case, Erin Brockovich, a legal clerk-turned-environment activist who helped to build a massive, multimillion-dollar case against California's Pacific Gas and Electric Company in the early '90s.

Hilary Swank, 2000

(Photo via Kevin Mazur/WireImage)

Hilary Swank, 2000

Swank won the first of her two Oscars in 2000, for the 1999 movie Boys Don't Cry, which was based on the real-life story of Brandon Teena, a transgender man who was raped and murdered in 1993.

Gwyneth Paltrow, 1999

(Photo via Jim Smeal/WireImage)

Gwyneth Paltrow, 1999

Paltrow won over Academy voters with her star-making turn as Viola de Lesseps, William Shakespeare's fictional muse in the romantic period drama Shakespeare in Love.

Follow Brit + Co's coverage of the 98th Academy Awards on TikTok, YouTube and Instagram!

EXPLORE MORE OF BRIT + CO

Selfmade

Selfmade

A business accelerator for early-stage female founders with live workshops, 1:1 mentoring, online courses, and curated business support. Visit

B+C Newsletter

Subscribe to B+C

Get your weekly dose of inspo, pop culture, and creativity — straight to your inbox. Subscribe to the Brit + Co newsletter! Visit