The 5 Most Shocking Best Actress Oscar Wins And The History-Making New Champion

The landscape of Academy Award history was dramatically reshaped in 2025. The "Best Actress in a Leading Role" category, always a lightning rod for debate and celebration, crowned a new, unexpected champion at the 97th Academy Awards, providing a fresh, immediate talking point in the ongoing narrative of Hollywood's highest honor.

As of late 2025, the most recent winner is Mikey Madison for her transformative role in the critically acclaimed film *Anora*. This victory, which occurred at the 97th Academy Awards, immediately became one of the most discussed Oscar upsets in recent memory, solidifying her place among the legends of the screen and setting the stage for a new generation of cinematic excellence.

The Newest Golden Statuette: Mikey Madison's Historic Win

The 97th Academy Awards, held in 2025, delivered a stunning surprise in the Best Actress category. The award went to Mikey Madison for her powerful performance in the dark comedy *Anora*.

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Madison, who had previously been known for roles in films like *Once Upon a Time in Hollywood* and the *Scream* franchise, delivered a career-defining turn. Her win was considered a major upset, particularly as she triumphed over veteran Hollywood actress Demi Moore, who was a strong favorite for her performance in another highly-regarded film.

The victory by the relatively young Madison for a film that pushed genre boundaries underscores the Academy's recent trend toward recognizing fresh talent and unconventional roles. It also means that the previous winner, Emma Stone, who won the award at the 96th Academy Awards in 2024 for her role as Bella Baxter in *Poor Things*, held the title for just one year.

Unbreakable Records and All-Time Legends

While the annual Best Actress race is always thrilling, the category is defined by a handful of legendary performers whose records have stood for decades. These actresses form the bedrock of Oscar history, setting benchmarks in longevity, volume of wins, and sheer acting prowess.

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The Four-Time Champion: Katharine Hepburn

The undisputed queen of the category is Katharine Hepburn. She holds the record for the most competitive acting Academy Awards won by any performer, male or female, with a staggering four Best Actress Oscars.

Her wins spanned decades and genres, showcasing an unparalleled versatility:

• *Morning Glory* (1933)
• *Guess Who's Coming to Dinner* (1967)
• *The Lion in Winter* (1968)
• *On Golden Pond* (1981)

Her final win for *On Golden Pond* made her the oldest Best Actress winner at the time, at the age of 76.

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The Modern Masters: McDormand and Streep

Following Hepburn are two modern titans of cinema: Frances McDormand and Meryl Streep.

Frances McDormand is the only other actress to have secured three Best Actress Oscars. Her wins for *Fargo* (1996), *Three Billboards Outside Ebbing, Missouri* (2017), and *Nomadland* (2020) cemented her status as one of the most respected performers of her generation.

Meryl Streep, while "only" having two Best Actress wins (for *Sophie's Choice* and *The Iron Lady*), holds the record for the most acting nominations in Oscar history, with 21 total nominations, 17 of which were in the Best Actress category. Her consistent excellence and longevity make her a perpetual entity in any discussion of Oscar winners.

The Most Shocking Best Actress Oscar Upsets of All Time

The Oscars are not just about recognizing the best; they are also about the drama of the upset. The Best Actress category has provided some of the most genuinely shocking moments in Academy Award history, where the presumed favorite went home empty-handed.

1. Judy Holliday Over Hollywood Royalty (1951)

In 1951, the relatively unknown actress Judy Holliday won Best Actress for her performance in *Born Yesterday*. This was a monumental upset, as she defeated two of the biggest legends in cinema history: Bette Davis (for *All About Eve*) and Gloria Swanson (for *Sunset Boulevard*). Swanson's performance as Norma Desmond is still considered one of the greatest in film, making Holliday's victory a truly stunning moment that defied all expectations.

2. The Unprecedented Tie: Streisand vs. Hepburn (1969)

One of the most bizarre and memorable moments in Oscar history occurred at the 41st Academy Awards. Both Barbra Streisand (for *Funny Girl*) and Katharine Hepburn (for *The Lion in Winter*) received the exact same number of votes, resulting in the first and only tie in the Best Actress category. The sight of two legends sharing the stage is a moment of pure Oscar lore.

3. Olivia Colman’s Emotional Win (2019)

The 91st Academy Awards saw a major shock when Olivia Colman won for her role as Queen Anne in *The Favourite*. She was widely considered the underdog against the heavily favored Glenn Close (for *The Wife*), who had been sweeping nearly every precursor award. Colman’s genuinely surprised and tearful acceptance speech is now an iconic moment of Oscar history.

4. The Youngest Winner: Marlee Matlin (1987)

While not a traditional "upset," Marlee Matlin’s win for *Children of a Lesser God* was historic and unexpected. At just 21 years old, she became the youngest person ever to win the Best Actress Oscar. Her powerful, Oscar-winning performance remains a testament to the fact that talent knows no age.

5. The Latest Shock: Mikey Madison (2025)

As detailed above, Mikey Madison's win for *Anora* at the 97th Academy Awards is the most recent example of a major upset. Her victory over the established favorite, Demi Moore, echoes the kind of unpredictable excitement that has defined the category for decades.

The Legacy of the Best Actress Award

The Academy Award for Best Actress in a Leading Role has always been more than just a trophy; it is a cultural marker. From the pioneering days of Janet Gaynor, the first winner in 1929, to the modern, boundary-pushing performances of today, the award tracks the evolution of cinema and the changing roles of women in film.

The history of the category is a rich tapestry of groundbreaking performances, from dramatic turns like Halle Berry's historic win for *Monster's Ball* (the first and only African-American woman to win Best Actress), to comedic triumphs like Julia Roberts' victory for *Erin Brockovich*.

The annual announcement of the winner does not just celebrate a single performance; it adds a new chapter to a century-long story of talent, ambition, and the enduring power of the female lead on screen. The addition of Mikey Madison to this elite roster ensures that the legacy of the Best Actress Oscar remains vibrant, unpredictable, and forever compelling.