The 5 Most Shocking Best Actress Oscar Wins And The Unbreakable Records That Define Hollywood Royalty

The Academy Award for Best Actress remains the pinnacle of cinematic achievement for female performers, a coveted gold statuette that instantly cements an actress's legacy in Hollywood history. As of the current date in December 2025, the most recent recipient of this prestigious honor is Emma Stone, who secured her second win at the 96th Academy Awards for her transformative role as Bella Baxter in the film *Poor Things*. This category is not just about celebrating the best performance of the year; it is a battleground of star power, critical acclaim, and historical significance, often leading to some of the most discussed upsets and record-breaking moments in the history of the Oscars. The competition in the latest ceremony, which saw Stone triumph over frontrunner Lily Gladstone, perfectly encapsulates the unpredictable and compelling nature of the Best Actress race.

Emma Stone: The Two-Time Best Actress Winner's Profile

Emma Stone's second Academy Award win for *Poor Things* solidifies her position as one of the most versatile and celebrated actresses of her generation. Her career trajectory is marked by a blend of blockbuster success and critically acclaimed independent films, demonstrating an impressive range.

• Full Name: Emily Jean Stone
• Born: November 6, 1988, in Scottsdale, Arizona, U.S.
• Age (as of December 2025): 37
• Major Breakthrough: *Superbad* (2007)
• First Oscar Win: Best Actress for *La La Land* (2016)
• Second Oscar Win: Best Actress for *Poor Things* (2024)
• Total Oscar Nominations: 5 (3 for Best Actress, 1 for Best Supporting Actress, 1 for Best Picture as Producer)
• Key Films: *Easy A*, *The Help*, *Birdman*, *La La Land*, *Cruella*, and *Poor Things*.
• Recent Accolades (for *Poor Things*): Academy Award, Golden Globe, BAFTA Award, and Critics' Choice Award.
• Character in Winning Role: Bella Baxter, a woman brought back to life with the mind of an infant, who embarks on a journey of self-discovery and sexual liberation in Yorgos Lanthimos's fantastical film.

The 2024 Upset: Emma Stone vs. Lily Gladstone's Historic Bid

The 96th Academy Awards Best Actress race was arguably the most closely watched category of the night, pitting the established star Emma Stone against the historical significance of Lily Gladstone. Stone’s win for *Poor Things* was a stunning moment that defined the ceremony.

Lily Gladstone, nominated for her powerful performance as Mollie Burkhart in Martin Scorsese's *Killers of the Flower Moon*, was the strong favorite in the run-up to the Oscars. Her potential win would have been monumental: she would have been the first Native American performer to win a competitive Academy Award for acting.

• The Enduring Legacy Of Haylor 5 Shocking Facts About Harry Styles And Taylor Swifts Relationship 10 Years Later Sf662

However, the Academy ultimately favored Stone's daring, complex, and physically demanding portrayal of Bella Baxter. Her performance was a total transformation, charting the character’s evolution from an infant-minded woman to a fully self-aware, intellectual being. The win highlighted the Academy's appreciation for performances that involve significant physical and emotional risk, especially within a director's demanding vision like that of Yorgos Lanthimos. Stone's victory was a reminder that the "frontrunner" status is never guaranteed on Oscar night, adding to the category's legacy of dramatic upsets.

Unbreakable Records and the Most Decorated Actresses

To truly understand the prestige of the Best Actress Oscar, one must look at the women who have set the gold standard. These records represent not only acting excellence but also enduring careers that have shaped cinematic history, establishing a high benchmark of topical authority for the award.

Katharine Hepburn: The Four-Time Record Holder

The undisputed queen of the Best Actress category is Katharine Hepburn. She holds the unbreakable record for the most acting wins by any performer, male or female, with four Oscar statuettes.

• The Unseen Story Jessica Simpsons Battle For Privacy And Body Image In A Digital Age Mlvqa

• *Morning Glory* (1934)
• *Guess Who's Coming to Dinner* (1968)
• *The Lion in Winter* (1969) (Tied with Barbra Streisand)
• *On Golden Pond* (1982)

Her final win for *On Golden Pond* at the age of 74 also made her one of the oldest winners in the category, demonstrating a career that spanned decades of critical success.

The Modern Masters: McDormand and Streep

Frances McDormand is the closest contemporary challenger to Hepburn's record, having secured three wins for performances in *Fargo* (1997), *Three Billboards Outside Ebbing, Missouri* (2018), and *Nomadland* (2021).

Meryl Streep, while holding 'only' two Best Actress Oscars (for *Sophie's Choice* and *The Iron Lady*), holds the record for the most acting nominations of any performer, with an astonishing 21 total nominations, 17 of which were in the Best Actress category.

• Shania Twains Bold Statement Why The Star Chose Nude Photoshoots At 57 Qf9cg

The 5 Most Shocking Best Actress Oscar Wins of All Time

The Best Actress category is famous for its "bloodbath" races, where the perceived frontrunner often loses to a surprising dark horse. These moments contribute significantly to the award's lore and generate immense curiosity among film enthusiasts.

1. Olivia Colman for *The Favourite* (2019): Colman's win over Glenn Close (*The Wife*) was one of the most stunning upsets in recent memory. Close was a near-unanimous favorite, having swept all the major precursor awards, making Colman's emotional acceptance speech a truly viral moment.
2. Grace Kelly for *The Country Girl* (1955): Kelly's victory over Judy Garland, who was nominated for her career-defining comeback role in *A Star is Born*, is still debated by film historians as one of the category's biggest robberies.
3. The Tie: Barbra Streisand and Katharine Hepburn (1969): While not a single win, the 41st Academy Awards resulted in an unprecedented—and incredibly shocking—tie for Best Actress. Streisand won for *Funny Girl* and Hepburn for *The Lion in Winter*. Streisand's iconic "Hello, Gorgeous!" acceptance line is etched in Oscar history.
4. Marlee Matlin for *Children of a Lesser God* (1987): At 21, Matlin became the youngest person to win Best Actress, and the only deaf performer to ever win a competitive acting Oscar. Her win was a surprise that broke barriers and demonstrated the Academy's willingness to honor truly groundbreaking performances.
5. Emma Stone for *Poor Things* (2024): While Stone is a major star, her victory over the heavily favored Lily Gladstone was a genuine upset that dominated the post-show conversation. It proved that sometimes, the late-breaking critical momentum for a transformative role can overcome a season-long narrative.

The Enduring Legacy of the Best Actress Oscar

The Academy Award for Best Actress is more than just a trophy; it is a cultural touchstone that reflects the evolving role of women in cinema and society. From Janet Gaynor, the first winner for films released in the 1927/1928 film season, to Emma Stone's triumph in 2024, the category has tracked the history of Hollywood.

The competition is fierce, the debates are endless, and the historical records set by legends like Katharine Hepburn and Meryl Streep continue to inspire new generations of performers. As the industry moves forward, the Best Actress award will remain a powerful symbol of artistic achievement, celebrating the versatility, depth, and sheer talent required to become one of the world's most acclaimed film stars.